Dating Remarkable Friends

SOLO 65 Josh Gray-Emmer | Remarkable Friends


This week, Peter McGraw repeats one of his favorite Solo episodes, “Dating Friends and Sleeping with Strangers,” as a fitting close to his series on making remarkable friends. The episode reveals some of his early thinking about what makes a good friend. He and his guests, Josh Gray-Emmer and Lily Rains, present tips for developing friendships and building a community. You will learn: 1) how ancient Greek philosophers held friendships in such high esteem that sometimes surpassed romantic partnerships; 2) people’s early reactions to the podcast, and 3) what his guests do on Valentine’s Day.  

Listen to Episode #65 here


Dating Remarkable Friends 

Welcome back to the first repeated episode of Solo, it’s one of my favorites, Dating Friends and Sleeping with Strangers the Valentine’s Day edition. In addition to it being close to Valentine’s Day, a truly hateable holiday, I chose to repeat this episode because it is a fitting close to my extended series on Making Remarkable Friends. In this episode, you’ll get to know Josh, or as I call him DTLA Josh. He puts his friends first. You’ll learn about his unconventional approach to dating and sex, something that he is refreshingly unapologetic about. A lot of things happen in this episode.  

It reveals some of my early thinking about what makes a good friend. My guest and cohost and I present some tips for developing friendship and building community. You’ll learn a fascinating lesson about how ancient Greek philosophers held friendship in such high esteem that often surpasses that of romantic partnerships. In the end, it’s fun to hear about people’s early reaction to the launch of the show. Learn some answers to a couple of reader questions and you can hear about what my guest and cohost do on Valentine’s Day. I hope you enjoy the episode.  

Our guest is Josh Gray-Emmer. Josh is the Founder and CEO of Bridge, a fullservice agency specializing in community engagement, website development, and social media. He’s a veteran of the Sundance Film Festival with a film he wrote and produced premiering there in 1997 when he was eighteen years old. He’s also a resident of downtown LA and the host of the DTLA Dinner Club, a free celebrity chef dinner party focused on building community and not profit. Welcome, Josh. 

Thanks so much for having me. I appreciate it. 

Please welcome our new guest host, Lily Rains. Lily is a storyteller, arts educator, crafter of needlework, and maker of delicious homemade ice cream. Though soloLily loves to be part of an ensemble with a shared goal, be it on a softball field, in an escape room, or getting a play, movie, or television show made. Welcome, Lily. 

I’m glad to be here. 

I met both of you through other people. I met Lily at an event, dinner party called The Dilemma Dinner and she came recommended by one of my I’m Not Joking guest, Nicole Blaine. Nicole Blaine is one of my best because of Nicole. I almost cried in that episode. Josh, I met you through a mutual friend, Darwyn Metzger, who also was a guest on I’m Not Joking. 

I saw he got a shout out in your book.  

He did, in my first book. Josh and I met in DTLA and we were chatting about business and LA and so on. I had mentioned this secret project that I was working on. Josh probed and I was like, “It’s not that secret. I told him about SOLO. I don’t remember exactly the phrase you had.  

I prefer to date my friends and sleep with strangers. 

You said, “This is my life. I date my friends and I sleep with strangers. I said, I’m going to have you on. Here we are. By the way, the tentative title for this, I rarely start with a title, is Dating Friends and Sleeping with Strangers Valentine’s Day Episode.  

That’s what you should do for Valentine’s Day. 

We’re going to return to Valentine’s Day in the bonus material. We’re going to hold off on that. I’m sure Lily already has questions based upon that phrasing of Josh’s life. 

Is the way that you meet people different between becoming friends and becoming lovers? 

Lovers, it’s such a gross word. 

There’s not a good word. Lover is the best word. Hook up? 

Make out?  

Friends with benefits? 

Fuck buddy. Pillow buddy. 

I’ve never heard pillow buddy. 

You haven’t?  

I don’t think I have either. 

You share your pillow with a buddy. 

I’m going to try that next time, “Bro, do you want to be my pillow buddy?  

You’re cute. You look like you don’t have lice. Do you want to come and share a pillow, buddy? 

I’ll let you know how that goes. I’m never actively looking for a hookup with people in real life. I’m looking for friends. I’m looking for new, interesting, and unique people. I strike up random conversations with lots of people for no reason. There are groups of people out there who are like, “Some weirdo tried to talk to me at the coffee shop today.” Every morning, I get up, I walk to a coffee shop two blocks away from here, I read the news, and I have coffee for about an hour or two. I have met, at that coffee shop over the years, quite a few good longterm friends and it’s because they were sitting there and reading an interesting book or I overheard something a conversation they had on a phone. There was a guy there who had a coollooking camera he was playing with and I will strike up conversation, trying to suss out and be like, “You’re interesting. You’re unique in some way. I’m good at keeping and maintaining longterm friendships. For hooking up, I do that online. Thank God for GrindrIt’s unbelievably easy. Straight people don’t have any concept of how easy hooking up on Grindr is. 

We’re going to return to that. I know that the reader is like, Come on, tell me all. 

The reader and me. I’m like, I want to talk. No, not right now. 

We’re going to come back to thatThat idea is interesting to me. When I meet someone in a coffee shop, it’s usually someone I’m attracted to. It’s old school to meet someone in real life. Otherwise, I got my head down and I’m working on my writing or whatever it is and then I’m like, “She’s cute. I don’t know how I’m going to talk to her, given that no one talks to each other anymore 

Being a homo makes it easy. I can gay it up a little bit more to talk to a girl and instantly disarm. Guys as well. I’m not threatening. There are some distinct advantages in life to being homo, especially when it comes to making friends quickly and starting conversations with randosWomen are going to be instantly on guard with a straight dude because they think, “He’s trying to sleep with meWhat do you want? With a gay dude, they’re more intrigued. It’s like, “What’s going on here? 

For me, I can play in the sandbox and I can play on the soccer field. I want to know what game we’re going to get into. If you see me coming with my cleats, you know we’re playing soccer. I can hang out with anybody. I like a lot of people. I like a lot of things about a lot of people. I was told as a younger lady that I am a big flirt.  

You’re still a lady.  

I’m still at will. I’m a woman who seldom acts like a lady that your grandparents would recognize and the definition of ladylike behavior. Anyways, I am my own self. The point that I’m trying to make though is that as I get older, the micro boundaries that you have created so that you can regulate expectations and why you’re connecting with people and if I approach a couple, I usually am a little bit more focused on the woman so that it is less of a threat. That’s interesting that you found a chance to dialup or down. Do you feel that’s inauthentic or do you feel that’s a part of that barrier?  

It’s not inauthentic because it’s the test phaseThey’ll get to know the real me really quick if you pass the test phase. I’m trying the foot in the door and see if you’re cool, see if you’re interesting, what unique thing do you bring to the table. I’m never trying to hide who I am or not be myself because that’s a waste of everybody’s time.  

What does it take to pass the test? I’m asking for Lily. 

I want to be your friend. Can I be your friend? 

We’re friends already. You did it. Not boring, for God’s sake. That’s the only thing. I’ve met many different types of people in my life. Almost all people fall into specific categories. There are maybe twenty categories of people.  

That’s a lot of categories.  

I know. When you’re meeting thousands of people over a lifetime, it’s super intriguing that you can recognize the same type of person in your life over and over again. I would say that half of those categories of people are boring. The other half of those categories of people are fantastic, weird, quirky, interesting, and I want all sorts of them, all of them. All the people in that half, and none of the people in the other half. That’s all I’m looking for. 

You’re looking for an interesting person.  


This is a question that I wanted to get to. I like the fact that you are on the hunt for friends.  


The idea that you date your friends is an especially interesting idea that we’re going to also return to. You’re looking for interesting, intriguing, and a friend. Lily? 

I’m intuitive. If there’s a buzz that happens, that’s what draws me in. It is chemistry. Sometimes I can be stimulated intellectually. Sometimes I can be stimulated in fullon joy child play. I don’t do well looking directly into the sun. The thing that makes me really is sometimes what people want to set me up on a blind date about and that thing goes away.  

I hate any phrase that begins that way. It never ends well.  

Even if it’s platonic. For the most part, I will get along with people. If you set me up to say, “You’re going to love this personThey’re going to love youGo meet this person,” I have an expectation, it dims my light, and I’m not vibing at my authentic frequency. That’s where I say, “Let’s have a secondary focus, a game night, dinner, or a thing.” You can show up and witness each other in space and interacting with others and that’s where I’ll be like, I do want to hang out with you romantically or platonically.  

I almost never hang out with people that I meet in any oneonone situation. I’m always inviting them to a dinner club, which is a great thing to have as a regular thing that I do every Wednesday. Having 30 people over to my home for a celebrity chefstyle free dinner party is an excellent way to bring someone into my world, give them a little taste of my friends, and me without overwhelming them on me. I like dim sum on Sundays. It’s always a big group. I’m always doing something with a group of people. My groups are also different. Not all of my groups cross each other. I’ll think like, “You should join me on Friday for bro drinks.” Every Friday, I have anywhere between and 10 people over, depending on who’s available. It’s all bros. It’s an after-hour drink. 

Were you drinking like Aperol spritzrosé, mimosa, ciders? 

We’ve had girls over to bro drinks. I call it that because it’s super browieIt’s like, “What group thing that I’m doing are you going to most feel comfortable in? I’m doing lots of them. It’s like, “Come join for this. That’s test number one. You eliminate half the people right there because they don’t show up or worst, they say they will, and then they flake. Showing up, my respect level skyrockets. I know it’s hard to show up. It’s hard to do things. I give you a lot of respect for meeting me, saying you’ll do something, and showing up. I realized that’s difficult, especially when you aren’t going to know anyone else there. I promise all of my friends are cool though. 

You’ve done quite a few things in what you were sharing. You’ve created a community center of your life, like a social calendar. You show up for yourself. Your friends show up to be a part of it.  

It’s all consistency. The only way that you’re able to build and maintain longterm friendships is through consistency.  

You’ve filtered many people in different ways. You let the new friend/intimate partner filter through your community.  

Never an intimate partner. I don’t mix those two worlds. 

If I get invited to dim sum. 

I’m not sleeping with you. I’m attracted to dumdums. 

Not dim sums. 

I am not attracted physically to the people I would want to hang out with. I have friends who are also attracted to the same type of people. They’re heterosexuals. There’s this whole thing where they’ve got to go out on dates with them and bring them out to their things. I have the luxury of not doing that and I’m not going to imitate those purely heterosexual patterns. I don’t have to. I’m not going to. 

For me, the person I date and the person who becomes a friend share similar qualities. There’s something about them or something about the circumstance that guides them into one or the other. 

I have been physically attracted to someone that I met before and I was like, “You’re hot. I go over and I talk to them and I start to get to know them. They come meet up for something and they’re smart and interesting. By the end of that first hangout, I’m no longer attracted to them. Now they’ve moved to the friend category, “You’re cool.” 

All of a sudden, you trust their judgment. What is the thing that is now adding to the physical attraction that then turns you off in a chemical way? 

I’m specific on what I’m physically attracted to 

You have a type. 

You’re sexually intimate with somebody.  

I don’t ever want to see them again or talk to them afterward.  

For you, you’re okay with this?  

It’s awesome.  

He’s more than okay with it. He brags about it. 

The sex is amazing. The plentitude of available dumdums out there is staggering. 

In the meantime, I still need to find good dim sum. 

I will show you NBC Seafood in Alhambra where the Chinese people are. I keep them separated. The only time that they crossover is when I happen to have in the past experimented with straight friends. I feel honored that they’re coming to me to try that out. It’s a little worrisome because I want to screw up the friendship. The great thing about most straight dudes is they’ll pretend it never happened right afterward, which is great for me because I’m going to pretend it never happened too, “It was awesome. It was super fun. I had a great time. If you want to do it again sometime, it’s cool. There’s a code word all straight dudes have if they want to hook up and it’s like, “Bro, do you got any porn? It’s incredible how many times I’ve heard that. It’s great because they won’t talk about it again. You don’t have to destroy the friendship. Other than that, there’s no crossover.  

You don’t have to destroy the friendship because both participants agreed to have absolutely no discussion or vulnerability around it ever again. Are you vulnerable with your friends?  


You’re being satisfied in all the pistons that we have in life.  

have the ideal partner. I split them up into multiple people. I am fully loved. I feel love from my best friend from high school, Reyna. My best buddy, Greg, who I consider like a brother, we chat every single day. We text each other. We see each other only a couple of times a year. We chat about stupid things. We chat about life goals and things that scare us. If I got sick, I would have friends here who would help take care of me. I feel love and I give love to my friends. I’m great at maintaining incredible, fulfilling long term, twenty yearplus friendships. I have lots of those and I value them a lot. I took my ideal mate and I split them up into multiple people. 

want to come back to a few ideas here and one of them is this idea of what makes a good friend. This is something that I’ve thought about and talked about. Some of the things that make a good friend have come up. I’m stealing this word from Darwyn, who you knowwhich is they’re energizing. He uses the word energizing. You said intriguing, you said interesting, those are all good words. You alluded to two that I have, one is trustworthy. A good friend is trustworthy. You can tell them your secrets, that’s probably the most important of those things. The other one is reliable. You give them a test, which is to come to dim sum, come to bro drinks, come to the DTLA Dinner Club. Do you have any other regular things?  

Dinners and hanging out. 

People show up. They say they’re going to be there and they’re there. 

I have little tolerance for flakes. It’s an LA thing for people to flake. People don’t understand the difference between flaking and canceling. They’re different things. Canceling is calling and saying, “Excuse X. I won’t be coming. Sorry, I don’t mean to waste your time. Canceling within an hour, I consider flaking and/or hitting me up afterward and saying, “Sorry, I forgot.” True flaking is where you pretend it never happened and you didn’t say you were going to come to that thing. I have no patience for that. 

That’s the reliability box. The other more mild form of that is someone who’s consistently late. They believe their time is more important than that with a group. 

I was depressed in my mid-twenties. I was seeing a shrink. I’m a big fan of psychiatry. I was depressed because I thought that I was willing to give all of myself to my friends and they weren’t willing to give it back to me. My shrink helps me understand that I didn’t know the difference between a friend and an acquaintance. They are not the same thing. They’re two different things. My brain thought they were one thing. As soon as I was able to separate it, “You’re an acquaintance. I love hanging out with you. We have a ton of fun.” I meet you at the club. When I was younger, I used to go out and party more. You don’t want to know if I have something bad going on in my life. You’re not going to come and pick me up at the airport when that matters. 

You asked how I was and stuck around for the answer. 

It’s worse than that. You call me and then the conversation doesn’t end with you asking for something. An acquaintance will call you and ask for something at the end and that’s okay. You still like them. I have acquaintances I thoroughly enjoyed but they’re not friends. Soon as I was able to make that distinction, my whole life improved and it’s been better ever since. 

This is a good one to the fourth. I added this one to the list and I can’t take credit for that. For the first three, I’ll take credit for although the energizing term is donated by our friend Darwyn. The fourth one, I’m slightly embarrassed to say this but I got it from Jordan Peterson. Jordan says, “What makes a good friend is you can share the good news with your friend and they’re not jealous. They’re happy for you. They’re not going to go, ‘That reminds me of the time where this better thing happened to me. The other one is you can share bad news with a friend and then they’re going to try to support you and help you. That’s a great way to think about the strength of your friends. 

He’s not wrong. I find that to be truthful to me. I’m single and I don’t ever plan on getting married and I don’t ever plan on dating in the traditional senseI don’t do conventional or traditional type relationships at all, I’ve never done it, I am able to maintain stronger and longterm friendships. I have the bandwidth. It’s a bandwidth issue. 

That is a huge part of it. I have a new group of friends that we were all working together over the summer. We’ve remained close. The reality is that even though some of us are partnered up, nobody has children. That ruins everything. 

Let’s step back for a moment and talk about the evolution of how you got to where both of you are. I see some similarities between the two of you. Youre solo and you’re focused on community. Lily, in your bio that you sent me, you used the word ensembles, which is fun way to say community, group, team, etc. This is central to who you are, Josh.  

It’s part of my identity at this point. 

I’ve had some family issues in life. I’m more likely to be single than partnered up, so I’ve always leaned heavily on a group. Whenever I moved to a new place, I worked hard to try to develop and facilitate and build that. Why don’t we start with you, Lily? Has this been an evolution? Have you always done this? What’s your origin story?  

I’m familyoriented. From a young age, if I were ever a part of anything like a school show that went down or closed or the soccer season was over, I would always be depressed. As I get older, I look back and I do have a lot of different groups of friends. I make friends easily. I’m only now able to say, I build communities. My love language is quality time. If I’m spending quality time with you, we are a community. I often have people crossover easily. There are a couple of times where they don’t cross over and I’m like, I don’t know if I want to spend time with you because you don’t fit into other pockets in my closet.  

got to be honest with you. I don’t know if my community comes from a place of me exploring my place in the bigger, grander scheme of things. I love being a part of something bigger. That’s faith. That’s spirituality. I’m not conventionally religious or spiritual person. I stay in the question of, “Is this my codependency?” I’m okay with that. There’s real negative connotation to codependency. I was in a relationship for ten years. There was a lot of codependency and a lot of growth that happened over those ten years. I’m grateful for it. I’m also grateful I got out of it. I do appreciate relationship. I would love to be in partnership but I am also committed to being on my own. I’m not interested in sharing my most intimate energy until I’m comfortable knowing where my natural energy is mine versus what I take on from others. I want to make sure I can define who I am in the positive independently as opposed to in reflection of everybody around me. 

I have this phrase that I came up with about being single for now or forever. You two encapsulate both of these things. Lily, you’re a for now person. Josh is a forever person.  

It does sound like that. Josh is trying to save his cats from feeling claustrophobic inside of the house. 

That helps to set the scene. We are sitting on Josh’s couch in his loft in downtown LA where he hosts his Dinner Club. This is weekly 

I was lucky enough to buy this in 2010 during the market crash. I have a beautiful rooftop that I own and I have seating for 30 up there.  

You do 15 friends and 15 strangers.  

It’s an excellent way to meet new people. Fifteen people sign up online and then there’s a waitlist. I’ll go through the waitlist and pick my friends and other interesting people from the waitlist. It’s fifteen random strangers, which is exciting every time, and then fifteen people who have been before or who look super intriguing. People fill out a little questionnaire and I read every single application for Dinner Club and mark people’s profiles. Everyone has an equal opportunity to get in. 

You curate the evening depending on the interesting things.  

I spenseveral hours doing the seating chart. Everyone is seated based on who I think that they would have super interesting conversations with. I always separate couples because they’ve had the same conversations over and over again. I want them to have a new conversation and then go home and talk about what their experience was. I try and sit people together who are from different jobs.  

Don’t put all the entertainment people together. 

They’re going to shop the whole night. They can do that during cocktail hour. It’s super fun for me to do. I always get such a kick when I see people at the end of the night exchanging numbers. People hang out. People have gotten jobs. Chefs work together. It’s fun to be that instigator for that. 

The thing that I have to say is that even reading and hearing your bio, you’ve been clear on being a community builder. 

In my origin story, it’s super easy. I didn’t have a single friend until I was sixteen. I was bused to schools with kids I didn’t like. There were no kids in my neighborhood. I was super alone and own my own. I was a latchkey kid. In junior high school, I discovered there was a film program. At first, I was on stage crew and I started to make friends. I went to Pacoima Junior High School in the hood. I was happy to be there at a magnet program with thousands of kids so I could disappear in all of the random wacky kids. I got to go to my first Sundance Film Festival when I was thirteen and I was like, “This is what I want to do. I’m going to get involved in film. The whole process from 13 to 18 was going to movies with friends, organizing all of my friends into making movies, hanging out on film sets, and all that stuff, which was my first foray into having friends at all. I was the instigator because I desperately wanted to have friends. I got started early figuring out how to make friends and build those friendships around things. I got a leg up. I did more of that in college. As soon as I was out of college, it was continuous. 

That supports the theory that friends out of work relationships are usually healthier, longer sustaining than work out of friendships. There’s something about being able to show up for each other on time, follow through on the task at hand, and also speak to what your strengths are, what your interests are, what you’re not good at. Challenge one another. If you talk about the friendships that haven’t lasted long, in even those few descriptions you could go, “That’s where we fall apart. Someone didn’t show up for me. They didn’t tell me that they couldn’t handle the stories that I needed to tell.  

Let’s finish your origin story because we’re missing something from yours, Josh, which is where you decided to put up this Chinese wall between your friends and your penis.  

Is there a glory hole in the wall? 

That’s the whole point. I’m not sticking it through the wall.  

There’s been a few holes. We’ve taped them up. 

For the readers, I’m not going to explain what a glory hole is. Be careful googling it on your work computer. The other one is, what is a Chinese wall? For example, magazines and newspapers have what they call a Chinese wall. I don’t even know the origin of it. The editorial decisions and the advertising decisions are completely separated. It’s not going to stop you from writing a bad article about someone who might be buying advertising from youWhere did this come from?  

When I was growing up, when I was young, I thought I was going to be married with two kids. I had that traditional picket fence idea for myself and then I started to realize I’m gay but I didn’t want to be. I was sleeping with girls at fifteen. 

At least one of us was. 

This girl knew I was gay. She was taking advantage of it. How can you take advantage of having sex with a fifteen-year-old dude? She was nineteen. She wanted to get work on my film. She was an assistant at Barbizon Modeling School. I gave her work on the film.  

Those days are finished. 

She #MeToo-ed me? 

No. It sounds like there was consent across the board.  

Lily, thank you for arbitrating that 

I did it to be cool. I wanted my friends to think I was cool. I was trying super hard not to be gay. I started hooking up with dudes in college and then I discovered the interwebs. I was like, “This is way better. I never wanted anyone to stay the night. I never wanted to build on anything with anyone I was hooking up with. It was always like that. It took until my mid to late twenties to realize that. My shrink was like, “Why don’t you try it. There’s this dude who’s into you. Try dating him.” We dated for two weeks. 

You didn’t want him to stay over. 

It was the freaking worst and I was miserable. I was like, “I don’t want this type of life.” 

How long were you with that shrink, by the way? 


Male or female? Gay or straight? 

Male, gay, top-level shrink. He was fantastic. He’s not one of those, “How does that make you feel?” 

He wasn’t giving you a mandate to go try to be conventional. He was giving you a challenge to go experiment. 

It was helpful because afterward, I was like, “I don’t want this.” He’s like, “That’s okay.” 

One of the problems with therapy is that a lot of therapists bring their own bias to the table, which is a partnered life is a better life, so everything is seen through that lens. The interpretations of toughing it out in a relationship or the way you should go about meeting people, and so on. If you can have a therapist who’s agnostic, has no opinion, and indifferent and realize there might be a solo path for you, then suddenly his or her advice can change. Even if the advice is, “We’ll give it a whirl to make sure that this is the right path for you.” 

I would say that also one of the values that you’re talking about with your friends would be, “Can you listen to me and not make it about you?” One of my best friends, as close to being Christian as you can, she defines herself in a different way, but I’m not and we have great conversations about spirituality and religion.  

One of my best buds, August, is a lifelong Catholic or Christian. I always have trouble telling the difference. One of those. 

Catholics have more guilt. That’s all the difference. 

Whichever one has the big churches. 

If they look like they’d be painful to fall on, Mormon. 

I love Mormons though. They are so nice and friendly, but I’m not religious. We have an excellent conversation. He’s a credible friend and his faith helps him be a better friend. Whereas, I’m totally a completely, hardcore atheist.  

Your values overlap. You might have received your values because you were taught them in Sunday school. You might have received your values because you were taught them in grad school while you were getting your Doctorate in Psychology or whatever. I don’t know where you would have gotten them. I got mine from family. 

I don’t know. My family was messed up. My parents were great. I just didn’t have an excellent model, so to speak. They both loved me much, which helps a lot. I don’t think they loved each other much. 

I want to make sure you finish your thought about your friend who’s close to Catholic. 

Not Catholic. 

Close to Christian.  

She doesn’t celebrate anything pagan. The idea that you can still be close to someone and share your most intimate details, even though the other person would never in a million years condone that behavior for themselves, but be able to help you navigate. Whereas, Nicole Blaine and I have similar values. You can show up for each other and be like, “Do you want me to listen? Do you want me to hold on to this information? Do you want me to give you advice or do you just need someone to vent on?” At some point, how I deal with my therapist is, “I’m going to give you with the download. If you could reflect back to me what I’m doing well, that’d be great.” Sometimes, I’m like, “I need a new thought pattern. Get me out of this.” When I called you, I was like, “I want your perspective on this.” 

I didn’t charge Lily. She can’t afford me. 

I get a lot of value out of having friends who severely disagree with me on those things in my life. I have hardcore conservative Trump friends and I get a lot of value out of it. I have friends who are religious and I have friends who are different from me in almost every way. We are still lifelong good friends because we don’t judge each other on the things we disagree with and I can have those conversations with them. They just have to be smart, respectful, genuine, and the things you were talking about. Also, reliable and energetic. None of those things that you talked about relates in any way to how we feel about the world around us, so I’m happy to have those types of friends. My life is better for having those types of friends, even though we definitely don’t see eye-to-eye on almost everything. 

I want to tell a quick therapy story. This came up in episode one, which is that a solo person should have a team, the idea that you want to have a team, and a therapist is an integral member of the team. I recognize that, for some people, is a luxury. Therapy may be expensive. 

Who’s your money person again? 

Money Amy.  

You didn’t put Money Amy’s info in the bottom. I need Money Amy’s info.  

Good news. She’s going to be in an upcoming episode. She’s going to get a lot of work. If you haven’t read episode one, I talked about a financial advisor being part of your team and I have a particular type of financial advisor, which is fee-based. You pay them by the hour. You don’t pay them a percentage of your wealth. I have a strong opinion about that. I have this great therapist back in Boulder. He’s a poet. I give people nicknames. One day, he was helping me with my relationship with my mom, which was the thing that brought me to him. I need to try to repair and improve this relationship. It’s making me deeply unhappy.  

I remember him giving me a piece of advice about how to deal with something and I said somberly, anxiously, a furrowed brow, “She’s not going to like that.” He said to me, “Be that as it may. I’m not here to make your mother happy. I’m here to make you happy.” I started crying and I was like, “This person has my back 100%.” It changed our relationship because I was like, “He is my advocate.” If you get the sense that your therapist is not 100% there to improve your happiness and well being, they might not be the best therapist for you.  

I’ve pitched therapy to lots of friends and the thing that I always say is it took me five to find the guy who kicked ass for me and changed my life. 

You have to date a little bit. 

Yes, you do. If you find the best person on number one, God bless. Great job. When you go see the person, give them a couple of times, and move on, you’re allowed to say, “You’re not right for me.” 

You’re doing them a favor, too.  

You’re paying. I was paying money. When I’m paying someone something, I have a strong feeling about getting my money’s worth, so I was like, “We have an hour. You’re expensive. Let’s do work.” 

I want to jump back into this sleeping with strangers thing because we’ve been teasing the audience with this. First of all, I want to say this as a straight man. This is a different world that you live in with Grindr. If I were to say, “I date friends and I sleep with strangers,” I’m not doing much sleeping in that metaphorical sense. Grindr is, in your world, doing this with your dum-dums that you affectionately refer to these guys. 

I love them. That is not a negative term. God bless them for being such lovable cuddly dum-dums. 

How does this go down? 

I will turn on my phone and I will turn on Grindr. It will start beeping and I will pick out what I want. They will show up and we will hook up and they will leave. The whole thing happens within an hour. 

By the way, I do this with Postmates. 

Is Postmates for dick? 

Yes, with a better selection. It costs no money. It’s so much more honest than a lot of straight people’s dating. 

You’re talking about primal connection. 

We say immediately, “Here’s my face. Here are my body and dick pics. What do you want to do? What are you into? Can you come over? Are we doing this now?” There’s no exchange of, “I’m going to buy you dinner,” as a pretense to, “We both know where this is going.” I see such drama, the dance that straight people do. It seems so exhausting.  

This is in line with what Dan Savage says. Do you ever listen to his podcast?  

I don’t. I know I should. Everyone says he’s amazing and the best.  

He has helped me navigate language and identify what I would like and all the things. What he says well is that straight people will never have as good of sex as gay people because straight people hear consent and stop talking, even though they have completely opposite body parts. Whereas, gay people hear consent and start talking. “What do you like? How do you like it?” They put words to it, even though they’re dealing with much the same exact apparatus. 

It does help that we have our own equipment and we know what to do with it. I’m, for example, exclusively a top. Plenty of people are exclusively bottoms or bi or vers or whatever. Everyone has their positions and preferences. You have to talk about that with someone right off the bat. Two tops don’t make a bottom. That’s not going to work. You have to discuss these things in advance and there’s no shame around any of it. There’s so much shame, especially unfortunately for women. 

Sex in general. It’s not exclusive to one sexuality or spectrum. 

Americans especially.  

We’re repressed. That’s ridiculous. 

I got a text message from a German woman. My buddy had introduced me professionally and she read the non-monogamy episode. She’s like, “You too sounded like a couple of Americans talking about ethical non-monogamy.” I’m thinking to myself, “That’s what we are.” In the United States, this is a revolutionary idea. In Berlin, it might be like, “Yes, of course.” For the average person, they never thought of this. 

Berlin has the greatest club in the world where it goes from Friday until Monday and there’s sex, nudity, drugs, and whatever the hell you want. They’re on top of their shit there. I’m jealous. 

You’re on top of there. 

To me, luxury is not the right word, but your ability to date friends and sleep with strangers is in some way enhanced not only by your sexuality but then also because of technology. In part, now you can sift through the options, and then you can communicate your preferences, exchange the pictures, and make sure everything’s up to snuff. 

I would like to push back on the idea though that this lifestyle is only open to homosexuals. 

Agreed. That’s what I want to discuss. 

I didn’t say only open. 

No doubt easier. 

Tinder was the heterosexual response to Grindr. Tinder came in after as far as my awareness of it.  

I didn’t know that. 

The same company tried to do one for straight people and it failed.  

It’s only men on there? 

No, it didn’t work because women were worried about other women seeing them on this app that was purely for sex.  

Is that real or did someone say that? 

I got on and saw it when it was on. It lasted six months and then they folded it. 

The idea that the narrative around that? 

At the time, I remember reading an article about it, so who knows what fucked things were based on data? 

I’m not mistaken, Tinder was created after Grindr, and Tinder is successful. I know quite a few men and women who use Tinder in a similar way to Grindr.  

The key to being successful and I’ve helped friends with this before on those types of dating apps is to be completely honest and upfront in your profile. You’re going to eliminate 90% of the people, but the 10% that you don’t eliminate are there exactly for what you want. Now there’s Feeld, which is a whole new dating app for couples and threesomes and more, which is heterosexual positive. There are lots of things you can choose from like heteroflexible, homoflexible, polyamorous, non-monogamous. Feeld is a fantastic new app that’s in between Grindr and Tinder. It’s for everybody. It only works in major cities where there are enough people on it. 

People who are in that conversation with themselves. 

I find Feeld to be one of the most sex-positive spaces on an app that I’ve ever seen. It’s fun to see. 

When we were talking one time, I knew that I wanted to have you on here, besides this is an interesting way to live your lifeI want to highlight folks like you. In some ways, it gives people permission to think differently. You started out thinking you were going to get married and have two kids and now you’re living a life that’s quite different than that, but no less rewarding and in many ways, much more remarkable. Some of this is through the hard work that you’ve done, understanding who you are and what you want, and then some of it comes a little bit from the help of technology.  

This would have been a much harder lifestyle to lead if you weren’t in a place like Los Angeles and you didn’t have mobile phones. I want to do a little mini-lecture here for a moment, and then I want to ask you two a question about developing friends, not picking them. You can work on that while I do my talking. I want to give you two a high compliment and that is that the philosophy that you have, this solo philosophy of friendship, has existed for a long time and was spearheaded by Epicurus, the Greek philosopher. Epicurus was a contemporary of Plato but was much different. He was much more inclusive. 

While other philosophy schools were exclusive, Epicurus would take anyone who wanted to study and learn like the poor, the prostitutes, and so on. He’s well ahead of his time, as you might imagine. We know of Epicurean in terms of things that are delicious and delightful and food, but that doesn’t give Epicurus his due. While Greek philosophers were interested in answering the question of what is a good life and what makes a good life, Epicurus was interested in what makes a happy life, what makes a pleasurable life.  

He attacked the assumptions of the day and these are assumptions that still exist now. The first one is he looked at partnerships and he saw not just the love and connection that exists in partnership, but the jealousy, envy, cheating, and misery that can happen within a partnership. He concluded that a partnership is not the path to a happy life, but rather, friendship is. Good and real friendships rarely have jealousy as we’ve already talked about. They’re often uplifting and so on. He said, “Away from partnerships, into friendships.” 

The other stuff he said which is less relevant to what we’re discussing is people work hard to earn money. What he essentially says, “The better work is work to improve the world. To work hard to improve the world is uplifting as pleasurable as good. Working hard to earn money is a grind.” The other one is Greek philosophers talking, “We’re too obsessed and interested in luxury and we’re not interested in having a calm mind.”  

If you think about it, these are still issues that we’re tussling with today where people are talking about meditation and the value of meditation and how difficult it is as a path to living a more enjoyable, pleasurable life. The reason I bring this up is the notion of living a happy life, if it rests from an Epicurean standpoint on the shoulders of friends and of community, you are two people that I see as building community. Josh, your story is clear in this way. For Lily, I’ve seen it in just a small dose. I got invited to a holiday party that Lily was hosting and she made her homemade ice cream at it. 

I’m excited to try some.  

Let’s do that.  

I love ice cream. 

It was a delightful affair with wonderful people, and then she did something that I thought was neat, which was one of her friends is in an improv group called The Resistance. They improvise an action movie based upon an audience suggestion. Lily, at some point, shut the party down, gathered people up, and we drove to UCB, Upright Citizens Brigade, to see The Resistance. 

You guys didn’t know you were going to do it? 

It was a reveal that happened about 24 hours at a time. If you’re still here at 8:00, we’re getting into cabs, Ubers, and Lyfts. 

It was a thoughtful party in terms of food and drink and introducing people. Lily was hustling. 

I appreciate the amount of work. 

I suggest that we hire a bartender for the next. 

It was appreciated. You know how people show up. They’re like, “What can I bring in?” You’re like, “First of all, you’re an adult. Just figure out what you want to bring. Also, if you’re going to bring something, bring it having been made. Don’t make your shit in my house after I clean and take things out of the oven while you’re now dripping all of your things.”  

Do you want to name that person?  

There was not one person. 

I realize that with Dinner Club and with all of my events, I do multiple emails progressively giving more information and my emails are also clear about flaking. My Dinner Club email, the one you get on Monday before the Wednesday dinner said, “This is your last chance to cancel. If you flake, you can never return to a Dinner Club. 

We’re going to get back to my question about developing friends. I do this thing called The Dilemma Dinner. It’s a new thing. Lily was part of it. This is a small intimate six-person gathering where we spend a Sunday evening working through puzzles, problems that are professional or personal that each person has. There’s a lot of bonding and it was great. I have a line, which is, “If you miss any of my deadlines, you’re out. You’re uninvited.” 

It’s important. 

This is a privilege.  

You have 400 to 700 people on the waitlist. The chef is cooking 30 dinners whether there’s an empty seat or not. How unforgivable is it for there to be three empty seats, where there are hundreds of people waiting to fill that seat? I can’t ever let you come back. 

Thank you for valuing your time on this planet that led you to be the wonderful humans that you are. You’re valuing this opportunity. You’re valuing the chance to share time and space with you. It’s not coming from arrogance. It’s coming from, “I value this.”  

It’s for the greater good. 

If you tell people, they don’t do it. Ever since I started being firm on this, people stop flaking. 

We’ve talked about this idea of the importance of community and how much it can add value to your life and it can fuel you as an alternative to a traditional partnership. This happens to me where I go, “I want Lily to be my friend. I want Steven to be my friend.” I make a decision. There is still a probationary period and so on. How do you do it?  

Consistency and reciprocity. You’ve got to give of yourself and have confidence that reciprocity will return in some unknowable way because it always does. It’s easy. I assume that I will always be the one reaching out to everyone and I don’t have any resentment towards that. It’s my role. It’s the thing that I can do that I have no problem with that helps keep my friendships stable, consistent, longterm, and long-lasting. I’m the one who sends out the text every Thursday or Friday morning to everybody reminding them about bro drinks.  

I’m the one who sends out the email saying, “We’re going to do dim sum in Alhambra on Sunday,” to all the people who want to come and then follow up with everyone. You have to be consistent about reaching out to the people that you find valuable. You have to be consistent about always having things that you do regularly that people can stop thinking about and just fall into the habit of being involved in it. That makes it so much easier for people to build and develop friendships with you. I have lists of friends.  

I just go down the list and I’m like, “I haven’t talked to that person in a while.” I’m a text message guy, so I have no problem doing conversations over text messages. I know a lot of people prefer phone calls or prefer in person. I’d prefer text messages and then in person. I want to text you for a bit, re-catch up with you, and then at the end of that text conversation with a scheduled appointment. I don’t drive so I have no problem Ubering to you or sending a car for you. That’s my favorite new thing to do.  

It’s such a baller move. 

It’s cheap. It seems like a baller move. It costs in UberX.  

It’s hard to say no. 

There’s no flaking when the car arrives. Consistency and reciprocity help develop good friendships. 

How about you, Lily? 

I know I lead with honesty and authenticity with myself. I’m not holding shit back. Acquaintances and friends get that. I know that I can show up. What I’m getting better at is sitting back and witnessing how you want to show up and going with my gut on that because I’m a good people’s behavior reader and I haven’t given myself enough credit for that. It got me into trouble, so here I was, thinking that I had a couple of great people in my life, including a boyfriend, only to find out, “Oh, no.” 

I have to say I fuck up every once in a while and I’m going to continue to do it. For me, the first big-time it happened, someone stole my camera from the Dinner Club early on and I stopped doing Dinner Club.  

This came up when we first met? 

Yeah. I was mad and upset and I felt violated and robbed. I was like, “Would I pay $3,500 to get Dinner Club back?” The answer was totally a yes. I tried to be better about, “I know I’m going to get screwed. You can’t let fifteen strangers into your life.” Every once in a while, I make a mistake and that’s okay. I acknowledged that I can’t be an open person. All of the great friends I’ve made were from letting my guard down, being open, being honest, and trying to build those relationships. I can’t get all of those awesome relationships without getting fucked every once in a while. When that happens, I just try to limit it. Fewer and farther between, in between getting fucked.  

It’s like you’re getting your 10,000 hours. You get your reps in getting to know people, making friends, and then getting your heartbroken, recovering, and moving on. How deep the heartbreak is every once in a while, not necessarily within your control. 

My recovery time is way better now because I acknowledge it’s a part of all the good. I can’t get rid of that part. 

The heartbreak when you fall in love with a person who is your friend, you have an amazing sexual connection with, who’s also a dear friend, and your adventure buddies. Your lives intertwine, and then your best friend from college, you Yenta to be the roommates new thing, and now you’re the quad squad. You’re hanging out all the time only to find out that he’s been talking shit about you to the girl you used to fuck. He’s been a total asshole to you, to your face, behind your back. He’s undermining you. 

Are you picking this all up?  

This happens. Yes, off the cuff. That’s a chasm. That’s hard for you. That’s where the recovery from that has been a little bit rougher. What a beautiful opportunity to witness as I come up with what layers of my own accountability and who I do and don’t want to spend time with. My bandwidth hasn’t been as big to carry as many people in my life as it used to be. 

I troll people, sometimes. I will troll new friends with outrageous statements usually around politics because I love politics. I work in politics. I consider myself a liberal, but I love challenging liberals on these ideas that they’re married to and how they affect the world, and how privileged that idea is. They’re so married to these ideas, so I’ll troll them sometimes and watch their heads explode. I have so much respect for the ones that realize they’re being trolled and/or have excellent comebacks to me and/or are bold enough to tell me to go fuck myself. I’m jousting. The one thing I don’t want them to do is to agree with me when I know they don’t believe it. I’m looking for you to push back, not to just yes me when I’m saying something fucking outrageous. Fight with me a little bit. Call me on my bullshit. 

I want to make clear, when you say troll, meaning you’re in person? 

Yes. There’s no way to read someone’s face. Only in person. 

There are all these dating advice columns and dating shows and all this stuff, but there isn’t anything like a friendship advice column. We hold these relationships up to this high standard like this is such an important thing, albeit a difficult thingand yet, a lot of our happiness rests on the shoulders of our friends. I sometimes joke, someone meets someone and they disappear for a while, which may happen. You’re infatuated with someone. 

This is where my sadness comes from, to be honest with you. My first roommate here was an incredibly good friend. He’s the one who started Dinner Club with me. We cooked every week for 52 weeks in a row. He lived here with me for two years, and then he moved to a building next door and he met a girl. He was friends with all of us, all of the initial crew that we met when we were cooking together. We now talk about him as though he died. We say, “Danny, rest in peace.” We miss him, but his girlfriend, now wife, and none of us were invited to the wedding, didn’t want him to hang out with us and he felt that was acceptable. One of my great friends that I’ve been friends with for a long time works downtown. He lives in Cape Town. He has acquired a fuck trophy, a baby.  

That is brilliant. 

I never heard of that term before. 

That’s what you get. 

It does seem like a lot of people like to yield that thing around.  

They hold it around. They’re like, “Look what I did. You never knew love until you had one of these things.” 

You don’t even know. I know it’s hard.” I know it’s hard. I’ve been in public before. That looks awful. 

Now I know that he’s going to be moving to the valley and I won’t see him a lot. It makes me sad. I know that a lot of my friendships, no matter how hard I work, they have an expiration date. 

I’d say perhaps. Middle age is hard. Building your career, being married, having one or more children, and all those things are hard, so some people make sacrifices. They have to jettison their friends. Others don’t. It takes a little bit more planning and a little bit more work sometimes, but it’s sad when that happens. 

One of my best friends, Greg, understood that this was something that was going to be hard for me. He met the love of his life, this incredible girl, Paige, and they’re going to get married. He is so conscious of our friendship that I have no worry that I’m going to lose him.  

It changes things.  

Of course, it will change and he’s going to have beautiful children and I’m genuinely happy for him, but I don’t have any worry with him because he was conscious of this fear that I have.  

He sat down to have a conversation with you. He’s a good friend. 

He’s like, “You’re not going to lose me. I’m going to be your bro.” 

There’s the sadness that you felt, and then you talked about jealousy. Maybe we’re using the wrong word to say jealousy, but I had one of my best friends living in New York. Anytime he’d come out to LA, I’m like, “You make time to see me,” and then at some point, that was an inconvenience for him, which is an indicator that we’re no longer that friends. It’s not reciprocity. We are not in the same space of each other’s lives. 

In your life, some people will move from acquaintances to friends and some people will move from friends to acquaintances, and that’s okay, too. The thing about that I had to understand that’s cool is that I have had some incredible long-term friendships that are now more like acquaintances and it doesn’t devalue any of the amazing times we had together. The incredible times we had for ten years, from 20 to 30, we’re never going to have again. We’re not that type of friend anymore. Our lives evolved in different directions, but it doesn’t devalue how close we were. That will always be something that we shared together. We were close. We were great, amazing friends. Maybe we can reminisce on that. Maybe we’re not those friends anymore, but it’s just as important and valuable to have those types of friendships, too, even if they aren’t forever. 

I want to do a few things. We’re going to have what I expect to be a spirited conversation about how you two approach Valentine’s Day. For the reader who’s curious about that, if you want to stick around, we’ll get to that. I want to do a quick update. This episode will be episode 7 or 8. We’re taping this with out and launched the day that we’re taping this. I’m going to do a little update on some of the responses that I’ve gotten. This has been my secret project for more than a year. It’s completely different than anything I’ve done. It certainly is something that I’m getting more comfortable with the idea of having put it out there in the world.  

I feel a bit of vulnerability. I’m trying to be more vulnerable. I didn’t know what response I’d get. I’ve gotten largely a positive response. First of all, compared to my other podcast, people are going crazy over this one. The other one is throwing words into the ocean but for this one, people are leaning into and I’ve gotten a variety of different messages. Here are the three messages that mostly I’ve gotten. The first one is something along the lines, “Thank you so much. This totally speaks to me.” I had someone say, “I’m crying listening to this.” I’m like, “Wow.” It’s easy to be like, “Maybe this is me and maybe I’m a little too different.”  

I felt alone my whole life feeling this way and knowing that I was never going to be in a relationship or traditional type person that way. I’m super happy that there’s stuff like this out there. This is awesome.  

Frankly, you are living a farout life compared to the average person and I wanted to put that out there as, “Look at the menu of options you have in this world.” The second one is, “Pete, this could be big. This is going to be big.”  

That’s what she said. 

That’s what he said. 

Who knows? I’m good at making things. I’m terrible at promoting things. I don’t know if you’ve been paying attention, but I feel the world is ripe for this message. 

You had said that you were going to help build a community around this and I’m excited for the launch of a website, or however you do that, whether it’s a Facebook group, or whatever you decide. I’m excited to meet and bond with all of those solo people who are going through their own different experiences and how we can support each other. That’s going to be a cool part of this. 

I’m taking my time with that because I want to try to build that. 

I want to echo that because I’m looking forward to the huge meetup. We’ll take something over. 

That would be fun to do. I agree. There should be a place for people to be able to talk about these things. I will tell you this, there is one resource that is currently available. It’s not mine. It’s largely spearheaded by Bella DePaulo, who was my second guest. 

She’s a scientist.  

Yes. There’s a Facebook group called The Community of Single People. This is not for dating. We give you tons of that stuff. The last one is, and this one is funny. In a lot of this, this has been the smallest of them, “I love the show and listening to it but I have to hide it from my wifeI was listening to it in front of my boyfriend. I felt bad because it made me want to break up with him.” 

You’ve got to put the oxygen mask on yourself before you can put it on anybody you’re traveling with. People don’t realize that you’re not going to be a good partner if you’re not a good person.  

I know. I got a kick out of that idea. 

The shame. 

Have you gotten any legit negative comments like from church people or something? 

No, I haven’t. 

Look at you totally assuming that it would be coming from church people. 

I know. I’m totally biased. It’s like, “You’re promoting single life.”  

Bella talks about that in episode two. She’s surprised that churches don’t lean into single people more. They’re family-focused.  

I found fascinating the stats that she gave about how most volunteer work was done by single people except where it was within a church crowd. 

That’s right. You’ve got a good memory.  

It’s good content. 

This is a good update. I asked readers, please rate, please review, especially on iTunes. That’s the number one place where people are consuming podcasts. I’m trying to make it new and noteworthy. I feel my worry is this idea is buried in a sea of podcasts. Getting the word out will be good for this and will be good for people like us. I’m going to experiment with a new thing. I did not prepare either of you for this. I’ve solicited some questions from the audience. The first one is from Steve.  

Steve, how’s it going? 

Steve writes, “I’m an unmarried man, and I don’t currently don’t have a partner. I’ve been invited to a good friend’s coed baby shower. I have something else that I would rather do that day. What do I do?” 

As a lady who has a vagina and all of her healthy organs intact, the expectation that I’m a baby person, I also work often as a mom as an actor. I am not a mom. I play one on TV. The expectation that I’m interested in your baby is rich and it’s not true. When someone tells me they’re pregnant I first go, “Did you want that? Is that good? Congratulations? 

I teach a Marketing Management course to MBAs and I talked about positioning and how you can’t assume based upon someone’s age, gender, income, you can’t make assumptions about what they value and what they care about. The example that I use is pregnancy tests. If you go to the pregnancy test aisle, the sexual health aisle, wherever that is in the pharmacy, there are two different types of pregnancy tests. They do exactly the same thing. They’re highly reliable and fast, which everybody cares about. There’s a pregnancy test for people who want to be pregnant and there are pregnancy tests for people who don’t want to be pregnant. The packaging with a happy baby on one. 

Does one costs more than the other? 

That, I don’t know. 

We’ve got to do a search.  

I bet you the one that doesn’t want to be pregnant is willing to pay for faster results even though the results are all the same. 

In 30 seconds versus two minutes. To circle back, I personally have my own journey. I’m not immediately excited for people when they’re pregnant. I wait to hear what you’re excited about. In that space as showing up as a good friend who does not make it about her, I’m okay navigating conversations to see where it is that you want the support. Do you want it now at the baby shower where you’re going to want the people that you love to show up as your community and make eye contact and let you know I’m here for you, I love you, I’ve got two hours with you and I’m off to my next thing?  

Are you going to need help making sure that you’re fed once the baby comes out? There are different ways to show up for people who do have babies so depending on your relationship, you’ve got to find out is this the time where it would help to be a part of the community? Also, if you’re interested in meeting people, I would suggest hanging out with your married friends and/or your partner coupled friends. It might be a chance to meet a single lady at this coed baby shower. 

What I hear you saying is, “This is a negotiation.” Steve should say to his friend, “How important is it for me to be there for you?” 

Steve should ask himself does he know that because I don’t know how close he is with this woman? 

I don’t either. It’s a good friend. 

I wish we knew if the friend was a male or a female friend.  

It’s a male friend.  

Even better. 

That’s helpful also because there’s an isolation that happens. The male friend is the first in his community to get into the baby world and now we’re saying goodbye for a little bit. This is some marker in this man’s life. 

It’s a ritual. It’s a rite of passage. 

Even to show up, give a high five and go to your next thing, it might be worth it for him to negotiate within himself and go with your gut. What’s your friend’s feeling about this? 

It also depends on what’s happening. My old roommate, Michael, threw a baby rager. It’s a coed baby shower with no gifts, no games, all booze. I went because they framed it that way. Whereas my buddy Scotty, I love him to death, before we met for bro drinks on Friday, he goes, “I have some terrible news,” and I said, “Jesse’s pregnant?” He goes, “Yes.” For him, it’s great news but for me, it’s terrible news because he knows me. I’m still going to go to his whatever baby nonsense they do because I love him. The answer to this is pretty simple. If you love this person, you go and you make sure they know how much you hate it. 

Give them a whole bunch of baby shit with a Groucho Marx mustache on the kid’s face.  

They should be fully aware that you’re there because you love them, not because you want to be. You don’t rub it in. You don’t want it to be uncomfortable or anything. It’s a simple thing. It’s like, “I don’t want to go. I have something much better to be doing. I love you and I will totally be there.”  

I want to offer something that splits the difference with both of you. You say, “Go.” 

He says it’s a good friend. He also didn’t say whether he has $400 tickets to The Book of Mormon or anything. He didn’t say what the other thing was. I’m assuming the other thing is missable. 

It’s not something he would rather do. To me, building on this idea of what makes a good friend, and your idea about honesty is there anything wrong with Steve saying to his good friend, “I’m happy if you’re happy but I’m not interested in going to this baby shower, but if it’s important to you, I will be there for you.” “If it’s not important for you, let’s get together in some other way to celebrate this in a way we’ll both be happy.”  

That is the correct answer. 

That’s fair.  

I think about my best friends. What they’ll say is, “I need you there. This is going to be horrible and I want you there,” or he goes, “If I were you, I would not come to this thing. Let’s do X another time.” I feel like a strong friendship can weather the fact that you can say, “I’m not interested in going but I’ll be there if you need me to be there. I’m also not going to show up grumpy.” 

Once you’ve arrived, you’ve got to be in it, otherwise why go at all? 

You’ve got to buy-in. Don’t be that guy. 

The doctor has the correct answer here.  

I wasn’t even going to try and answer this one. 

You found it because we spoke from our hearts. 

My first reaction was like, “Don’t go.” 

There’s a place for you to both show up as your higher selves. 

What’s interesting is your friendship could be better for you not coming or better for you coming depending on which one it is. This one is related to a theme here. This is through happenstance. Jane writes, “I’m interested in fostering more of a community and not rely on my dating life for things to do and people to spend time with. What tips do you have for me about how to create more community in my life?” This might be a bit more of a recap but for Jane, what would you say? 

Pick something you love doing. Set a time every single week if you can do it, and every other week, if you can’t do every week, and do it every week, even if it’s with you and one person, or you with ten people. The consistency of, “Every Monday, Jane does X,” whatever it is, “Every Monday, Jane goes to pottery.” “Every Monday, Jane does dim sum.” Whatever it is, pick something you love and do it with at least one other person and invite others then you always know when you’re out, “I do this on this day.”  

Invite people you think might be interesting, you’ll meet people at that thing that you find interesting. Do one thing, pick one thing, and do it every single week at exactly the same time and day or every other week, at the minimum. Once a month doesn’t count. It has to be every week or every other week. Even if only one person shows up, on some days, twenty people will show up. That’s how you build that consistent community. It’s the easiest and simplest way to get started on that. I highly recommend you do that. 

That’s a strong answer. 

I 100% agree. I’m a huge group activity person. If you can show up to sign up for the adult softball league, sign up for whatever that yoga retreat is, whatever that shared activity is if you’re looking to meet people who share your interest. 

I’m also okay with you doing something yourself. Instead of signing up for a group, which is totally okay and I fully support it. It’s the easier route sometimes too. Not everyone has the organizational skills. 

It’s one way to stretch yourself. 

I’m going to relocate to Minneapolis for a couple of months and I’m already looking at what’s a meetup around that. Yes, I have some family up there but also what else would I be in? 

Being at this same bar every Friday from 5:00 to 8:00 even if you’re there with one person or you’re there with twenty people, eventually, people know that’s what I can do on Friday.  


I also don’t want to make people think that drinking has to be involved. That’s not what I’m encouraging. I’m using bars as an example of something easy. It can be a coffee shop, a writing group, or anything. 

I do want to give an added tip to this which is, “Name it well.” Naming things is important. Bro drinks sounds more appealing. I’ve got to find out what bro drinks are. 

Another would be finding a nonprofit or someplace to volunteer. That also gets you into the community and service of others. It gets you out of whatever your shit is. 

Every time I’ve been depressed or I’ve gotten out of depression, it’s James Altucher’s book and I got out of it by calling people up and being like, “What’s going on in your life? What do you need? I’ve got lots of skills.”  

You have people to call. On the other end of the spectrum, if you were like, “I’m new to this town. I don’t have connections to humans, necessarily. I go to work. I work in a cubicle or I work from home, which is what so many people do?” How do you find your community? What I wanted to say a minute ago was look at any rom-com, in the ‘80s and ‘90s. There’s always someone leaving their apartment, throwing a coin to the newspaper stand, grabbing the thing, and grabbing their coffee.  

That’s how they all start. The alarm goes off.  

That’s consistency. That’s exactly what you’re talking about and that’s now in form. 

The key is to not get discouraged if you do it for a month, every single week, and you’re there with one person. Consistency allows growth, it happens naturally and inevitably. 

I have a saying, “Anything worth doing is going to be difficult.” I recognize that not everyone is a natural organizer. Sure. Stretching yourself and working to be an organizer is one of the best ways to create something, a community for yourself. I like the idea that you’re like, “I have this thing. I’ve named it well. It’s something that’s going to bring me joy and now I have to populate it.” It changes your orientation in life. For example, as I was saying you’re at a coffee shop and you’re on the lookout for someone cute. When you have a community event now, you’re on the lookout for someone interesting. 

You’re speaking to the thing that I always talk about when coaching or teaching young performing artists. You’ve got a light inside and it is up to you to make sure that you are fueling it and you want to share that with the world. That’s not going to come when you’re in your own space. When you’re like, “I’m looking for my number one.” When you’re pursuing something, as opposed to showing up and being curious as your authentic self.  

Asa single person, I’ve got to tell you one of my least favorite things, “You’ll find it as soon as you’re not looking for it.” 

That’s bullshit. 

There are so many times when I want to slap a bitch. 

You also have to be open. There’s an open energy, but your energy is usually open. I love singing it and yet I’m terrified of doing it in public. When I joined an adult choir, I had a lot more friends. For a beginner’s mind, it helps you look at the world differently when you’re doing something that you’re not good at especially when you’re now middle-aged and you used to be good at some things that you do for a living or consistently. 

This is Jane, right? 


Jane can rely on the fact that she is not alone and everyone else out there feels exactly the same way she does. Finding people is easy because everyone wants to be found.  

Jane, I’m sending you a high five right now. You’ve got this.  

That’s fantastic.  

You’re going to be great.  

Thank you, Steve, Jane, Josh, and Lily for your participation. 

This is super fun.  

We’re going to talk about what we do on Valentine’s Day. Thanks, everyone. Thank you both.  

For sure.  

Thank you.  

We’re back for a little bonus material. 

It’s exciting.  

We’re back. 

Josh made us Old Fashioneds. 

Lube us up a little bit for Valentine’s Day. 

My Old Fashioned feels fresh in my mouth. 

It’s delicious. I used some good whiskey 

Old by name only.  

This is launching around Valentine’s Day so I would spend about fifteen minutes or so talking, maybe it’d be five. It won’t be more than sixteen minutes. As solos, what do you do on Valentine’s Day?  

Mostly feel bad for people who are coupled up because of the pressure.  

I’ve been a couple up before and it was fun. The last one I was coupled up for, we had dinner and went and fucked our brains out. That was great.  

That’s what you should do on Valentine’s Day. 

That’s what you could do. 

That’s what you should do on any Wednesday night. 

You can always fuck first. You can eat all the food. 

That’s a Dan Savage thing. 

I agree with it. 

Anybody who’s ever dealt with bloating or IBS? Come on, you guys. You know you’re going to do much better on an empty stomach.  

If you had told me that this is the turn that this little bonus material was going to take.  

More like boner material. 

I’m going to have to say something on that. Everyone thinks I get laid after dinner club and I have never gotten laid off but after dinner club. 

Are you exhausted after Dinner Club? 

I’m exhausted and full. The place is a mess. The chefs are hanging out finally. We’re chatting, cleaning up and everyone’s like, “Dinner Club is so good for getting,” I’m like, “No, never. I’ve never gotten laid after dinner. Come to Dinner Club.”  

Maybe if you had a dinner club of oysters. That’s so solo and myopic.  

I’m afraid all these old fashions are kicking in. 

Not at all. 

Back to Valentine’s Day. 

I’ve got to lead with something. I’m lucky. My birthday is August 14th, which is exactly six months before or after, depending on your perspective, Valentine’s Day. What I got into the habit of doing was sending Valentine’s Day cards to people I love letting them know they have six months before they need to get me a gift. 

You celebrate a half birthday.  

You send Valentine’s Day cards? 

I have done that before. My dad and my brother laughed hysterically. They were like, “Shit, you sent us a warning.” I’m not a gift person. If you see something that reminds you of me, I would love to receive it. I’ll receive love however you want to give it to me but it’s fun in a comedic sense to subscribe to the notion of gifts. I’m also lucky because my family totally disbanded with holidays on the actual days so I don’t have to subscribe to Father’s Day on Father’s Day or birthdays on birthdays. 

Most people can’t get away from Valentine’s Day because it’s being pressed at you all the time, nonstop. As a solo person, I feel lucky that I do not have to buy the roses, plan the overpriced dinner to the restaurant you can’t get into, and buy the gifts.  

The service is awful because nobody wants to be there. You’re not getting double pay as opposed to Christmas or New Year’s. 

I felt it in the past, where I’m like, “I’m alone tonight.” As I’ve gotten older, that has definitely changed from, “Aww,” into, “Thank the Lord.” I do not have to deal with this as I watch all my friends hustle. 

Also, stressed the fuck out. I have a girlfriend from high school. I remember coming to school the next day going, “My dad is a baller.” My dad sent my mom a dozen daisies and one rose. He said, “In a world full of daisies, you’re my rose.” I was like, “Dad, that’s amazing.” 

What do you do as a solo person? What are you doing on your half birthday? 

I’m doing whatever is around at that time that sounds interesting.  

Are you doing any of these, now that it’s anti-Valentine’s Day, and they have all of these solo parties? I almost want to do that even less. I feel like that’s trying too hard.  

I find myself opening my arms to the people who are upset about not being coupled up and going well, “I’m ready to hang out if you want to hang out.” We’ll have a fun night and do something else but I’m not coming from a place of feeling lack because if there’s someone coming to me wanting to connect, I’m like, “Let’s do it.” I don’t care if I’ve known you for 20 years or 20 days. If you want to share your day with me, I’d love to and also what is going on that night because what’s lovely is the movement away from Valentine’s Day as a Hallmark holiday. It does at least allow for trivia night, stupid things to be happening that night, watching movies, or going to comedy shows. 

Comedy shows are good every day especially if you live in one of the cities that has great comedy shows like New York, Chicago, Los Angeles, Boston, Washington, Atlanta, Nashville, Denver. Lots of cities have great comedy and a comedy show is a win every time even if they suck it’s a win.  

You went out. You got out and you made eye contact with people you knew and didn’t know. 

I had this conversation. The beautiful thing about a bad stand up show is it gives you something to talk about. When it’s good you can talk about it. When it’s bad you can talk about it.  

It’s a story. Mediocre is the only loser in a comedy show. If it’s going to be bad, you want it to be bad. 

The reality is also there is a way to lose a comedy. If you sat in the front and the comic totally picked on you, it was that first day and you were outbid on something or whatever. 

You’re the story for everyone else sitting around you. 

Yes, but for you driving home, it’s not a good night. When he asked you if you loved me and you didn’t say yes, why did that happen? 

For me for Valentine’s Day, I don’t do anything. I’m usually one to sit at home, watch some movies, skip past the Hulu Valentine’s Day channel and hang out. If there are a couple of friends around great if we can have a couple of drinks, great. The key for solo people is to not feel pressure, resentment, or feel bad about the way you’ve chosen to live your life. There’s an entire industry making a billion dollars that day making everyone feel bad if they didn’t get the perfect gift, or have the perfect person. Get those dozens of overpriced roses, or make that reservation at that overpriced restaurant that has a special menu that is three times the normal menu price. 

They started making it three days ago so you’re going to bloat anyway. 

There’s a lot of IBS stuff coming out of your mouth. 

What does your body want to absorb on Valentine’s Day? I would much rather sit aroundespecially in this loft, making something together and watching Carrie, which is the best prom story because you’re like, “Fuck you, prom.” It’s another example of how especially America has bolded and highlighted something that I don’t give a fuck about. Honestly, I have spent alone time on Valentine’s Day sending out good vibes to people because I know that it added pressure to a relationship that wasn’t ready to get this dose of love in your life. That’s so inauthentic. 

What’s interesting is, the 1st or 2nd Sunday after New Year’s is the biggest online dating date of the year. There’s a 30% increase in online dating.  


What they attribute this to is this dual effect of coming out of the holidays where everybody’s like, “Is there someone special in your life?” There’s this familial pressure. The other one is, “Valentine’s Day is 5 or 6 weeks away.” 

People are planning for that. Is it that much pressure?  

It’s a little of that.  

That makes me so sad.  

Do you know what’s a few corners around? Your death. Are you going to let it pressure you? No.  

Josh, you lead with, “I feel bad for people.” There’s this interesting dynamic, which is, the people who win on Valentine’s Day are happy couples. To me, happy couples with wealth. If you’re a wealthy and happy couple, it’s a great day. It’s a chance to reflect and celebrate. Sometimes you take things for granted, and it helps to have an external force. 

This is the day that you appreciate each other. You’re wealthy enough to hire a babysitter, go out to a nice restaurant, get the nice roses, and the ring at Tiffany’s. 

I’m going to save up all my appreciation for you this week and I’m only going to give it to you on Wednesday. 

The idea of this show is not anti-marriage and not anti-couple. Let’s be honest, some people do partnerships well. They choose well, they’re generous, supportive, good partners, and so on. 

My friends, Danny and Dina figured it out. Whenever I go to their house and through the entire time, I’ve known them, I’m always like, “How?” I see lots of not working ones but they are a beacon. 

We should celebrate the folks who do it well. 

Also, celebrate the relationships that got us to the place that we are consciously solo now. Thank you so much for that. I don’t want that. I want this. 

The other two categories that I’ve always thought about, were the unhappy couples. I have some sympathy for the unhappy couples too because there’s a lot of pressure. Sometimes external forces do us a favor and maybe if it is the case, breaking up an unhappy couple. An unhappy couple breaking up is not a bad thing. There might even be a little bit of a silver lining in that. There’s the person who is not coupled and feels bad about it. This external force, you’re doing well, you’re fine on the 10th, 11th, 12th, 13th and suddenly, on the 14th, you feel your life is lacking something that’s there. I feel bad for those people.  

I’ve been there.  

We all have in some way, shape, or form. It’d be pretty impossible, especially as a young person. 

As early as January every store already has Valentine’s shit up. 

Are you seeing the effects? 

There’s nothing going on between now and then. 

There is stuff going on. 

There’s Presidents Day.  

There’s MLK Jr. 

What do you sell for MLK?  

You don’t sell it. 

How do you commercialize that? 

Sorry, Hallmark, you couldn’t figure that one out? 

That’s a hard one. I want to say is there’s a fourth category that I never considered until I started working on this project. That’s the people like us in the room who are unpartnered and comfortable. 

For us, isn’t it like any other day?  

That’s what I was saying. I was thinking about what I do. My typical Valentine’s Day is like any other day. If anything, what I probably do is I lean a little bit more into taking care of myself. Maybe I do a yoga class or I go for a walk. 

Self-love the shit out of yourself.  

I might have a quiet night or work on one of my secret projects. This is a night that I can be free. 

That’s a great way to look at it.  

It is. 

In terms of, “I’m going to celebrate the fact that I’m living a good life.” I’m going to stay away from the restaurants. I do buy flowers for myself every week as we should.  

Me too. 

Josh does it too. He’s got some orchids over there. 

I buy lilies for myself because they smell amazing. 

I like orchids, they’re my flowers. 

I like tulips.  

It’s hard to keep those alive.  

I don’t buy them often. They’re hard to find but that’s my go-to flower.  

Luckily, downtown Los Angeles is three blocks from The Flower Mart.  

Do you know the best day to buy flowers? 

The day after Valentine’s Day. 

It’s the best day to buy Halloween candy too. 

True and shit will last. 

The best day to buy ornaments is the day after Christmas.  

Josh, you answered the question on how you’re going to spend Valentine’s Day or how you generally spend it. Lily? 

I generally don’t have any consistency throughout my entire life because I’ve been on a gig that gives zero fucks about what holiday it is. I’ve been working, I became a server in the last few years. I do that and I’ll cater. I was working at Universal Studios as a tour guide, also still acting. It’s like all the jobs in the world. I am hustling. This will be the first time that I am without a job that I’m aware of. I’ll be with my dad and my bonus mom. I hope that whatever they want to do, I don’t get in the way of. I would be more than happy to be invited into whatever they’re doing because we play a pretty good throuple. 

Maybe you could play this episode for them. 


She’s not down with that.  

They know everything about me.  

I seeThat’s great. Get it all out.  

I would like to ask any awesome people in the Los Angeles area to visit DTLADinnerClub.com so they can join the Dinner Club and get in on the awesomeness. If you’re pretty cool, DTLADinnerClub.com. Come have fun with us. It’s totally free. Meet your friends and neighbors.  

I love that. 

Lily, anything you want to finish with? 

I’m glad to be here in the moment with you guys. Thank you for this. 

This is great fun. Thanks so much.  






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About Josh Gray-Emmer

SOLO 65 Josh Gray-Emmer | Remarkable FriendsJosh Gray-Emmer is the Founder and CEO of BridGE, a full service agency specializing in community engagement, website development and social media.

He is a 24-year veteran of the Sundance Film Festival with a film he wrote and produced premiering there in 1997—when he was 18-year old.

He is also an 18 year resident of downtown LA and host of The DTLA Dinner Club, a free celebrity chef.



About Lily Rains

SOLO 65 Josh Gray-Emmer | Remarkable Friends

Lily Rains is a storyteller, arts educator, crafter of needlework, and maker of homemade ice cream.

Though solo, Lily loves to be part of an ensemble with a shared goal: be it on a softball field, in an escape room, or getting a play, movie, or television show made.


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