Dating Friends And Sleeping With Strangers – A Valentine’s Day Episode

SOLO 8 | Dating Friends

Who is to say that there is one right way to go about dating? In this episode, Peter sits down with Josh Gray-EmmerCEO of BRIDGE, and new guest co-host, Lily Rains. Together, they talk about Josh’s atypical approach to dating and sex, in which he dates friends and sleeps with strangers. They also discuss what makes a good friend versus an acquaintance, and present tips for developing friendships and building a community. Getting philosophical, Peter presents a mini-lesson about how friendships can be superior to romantic partnerships—an idea as espoused by the ancient Greek philosopher Epicurus. If you stick around to the end, Peter reports on people’s reaction to the launch of the podcast. The three of them also answer a couple of listener questions and reveal what they do on Valentine’s Day.

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Listen to Episode #8 here

Dating Friends And Sleeping With Strangers – A Valentine’s Day Episode

In this episode, I sit down with a fascinating SOLO guest and a new guest co-host. We learn about our guest’s fascinating approach to dating and sex, in which he dates friends and sleeps with strangers. We discuss what makes a good friend versus an acquaintance and present tips for developing friendships and building a community. Also, to present a mini-lesson about how friendships can be superior to romantic partnerships, an idea of espousing by Epicurus, an ancient Greek philosopher. I’ll give you a report on people’s reaction to the launch of the show. We answer a couple of readers’ questions and my guest and co-host reveal what they do on Valentine’s Day. I hope you enjoy it.

Our guest is Josh Gray-Emmer. Josh is the Founder and CEO of BridGE, a full-service agency specializing in community engagement, website development and social media. He’s a 24-year veteran at the Sundance Film Festival with the 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 for having me. I appreciate it.

Please welcome our new guest host, Lily Rains. Lily is a storyteller, arts educator, crafter of needlework and a maker of delicious 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. Welcome, Lily.

I’m glad to be here.

I met both of you through other people. I met Lily at an event I do, a dinner party called The Dilemma Dinner and she came recommended by one of my guests, Nicole Blaine.

I’ve got to check that one out.

Nicole Blaine is one of my best. I almost cried in that episode because of Nicole.

She does that.

Josh, I met you through a mutual friend, Darwyn Metzger, who also was a guest.

I saw he got a shout out in your book.

He did indeed in my first book. Josh and I met in DTLA and we were chatting about business and LA. 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 said, “I prefer to date my friends and sleep with strangers.”

That’s exactly right. You said, “This is my life.” He said, “I date my friends and I sleep with strangers.” I said, “I’m going to have you,” and here we are, so why not? The title for this, I rarely start with a title, is Dating Friends and Sleeping with Strangers: A Valentine’s Day episode.

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

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?

There’s not a good word. The lover is the best word.

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, some weirdo tried to talk to me at the coffee shop, but I have met. 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 long-term friends and it’s because they were sitting there, reading an interesting book or I overheard a conversation they had on the phone. There was a guy there who had a cool looking camera he was playing with and I will strike up a conversation and I will try to suss out, “Are you interesting?” It is unique in some way. I’m very good at keeping and maintaining long-term friendships. For hooking up, I do that online. Thank God for Grindr. It’s the easiest thing. People don’t have any concept of how easy hooking up on Grindr is.

We’re going to return to that. I know the readers were like, “Tell me all.”

I was like, “All the things I want to talk about, not right now.”

That idea is interesting to me because when I think about when I meet someone in a coffee shop, it’s usually someone I’m attracted to. That’s a very old school to meet someone in real life kind of thing. Otherwise, I got my head down and I’m working on my writing or whatever it is. When there was someone, I was like, “She’s cute.” I don’t know how I’m going to talk to her, given that no one talks to each other.

Being a homo makes it super easy. I can gay it up a little bit more to talk to a girl and instantly disarmed. To guys as well, I’m not very threatening. There are some distinct advantages in life to being homo for sure, especially when it comes to making friends quickly and starting conversations. Women are going to be instantly on guard with a straight man. They think, “He’s trying to sleep with me. What does he want?” With a gay dude, they’re more intrigued like, “What’s going on here?”

That is true. For me, personally, 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, but 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’m a big flirt. As an older person, I do feel that I have better.

You’re still a lady.

I’m a woman who seldom acts like a lady that your grandparents would recognize the definition of ladylike behavior. 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 dial-up or down. Do you feel that’s inauthentic? Do you feel that’s a part of that barrier?

It’s not inauthentic because it’s the test phase. They’ll get to know the real me really quick if you pass the test phase. I’m trying to foot in the door to see if you’re cool, to see if you’re interesting. What kind of unique thing do you bring to the table? I never try 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, that’s the only thing. I feel like I’ve met many different types of people in my life and almost all people fall into specific categories. There are maybe twenty categories of people, but 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. 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.

[bctt tweet=”The only way that you’re able to build and maintain long-term friendships is through consistency. ” username=””]

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

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

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

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

I almost never hang out with people that I just meet in any one-on-one 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 chef-style, free dinner party is an excellent way to bring someone into my world, give them a little taste of my friends, and of me without overwhelming them on me personally. I like them some on Sundays. It’s always a big group. I’m always doing something with a group of people. My groups are also very 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 5 and 10 people over, depending on it.” It is an after-hours drink.

Were you drinking Aperol Spritz, Rosé, and Mimosa?

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

You’ve done two things then. You’ve done quite a few things in what you were sharing. You’ve created a community center of your life with a social calendar. You show up for yourself and 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 long-term friendships is through consistency.

That’s showing up, but then you’ve filtered many people in different ways. You let the new friend/intimate partner filter through your community.

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

If you are going to, invite them to dim sum.

I’m not sleeping with you. I’m attracted to dum dums, not dim sum. I am not attracted physically to the kind of people I would want to hang out with. I have friends who are also attracted to the same type of people that because 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’m like, “I have the luxury of not doing that.” I’m not going to imitate those purely heterosexual patterns. I don’t have to. I’m not going to.

That’s an interesting idea because for me, the person I date and the person who becomes a friend share very 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 so hot,” and I go over and I talk to them and I start to get to know them. They come to meet up for something and they’re smart and interesting. By the end of that first hangout, I’m no longer attracted to him. They’ve moved to friends category, “You’re cool.”

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

I’m very specific on what I’m physically attracted to. I don’t ever want to see them again or talk to them afterward.

Are you okay with this?

It’s awesome.

He is more than okay with this. He brags about it.

The sex was amazing. The plenitude of available dum dums out there is staggering. I keep them separated. The only time that they crossover is when I happened to, I have in the past experimented with straight friends and I feel honored that they’re coming to me to try that stuff out. It’s a little worrisome because I don’t want to mess up the friendship, but the great thing about most straight dudes is they’ll pretend it never happened afterward, which is great for me because I want to pretend it never happened to. It was awesome. It was super fun. I had a great time. If you want to do it again some time, it’s totally cool. There’s a code word all straight dudes have if they want to hook up. It’s like, “You got any porn?” It’s incredible how many times I’ve heard that.

This is news to me.

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. Are you vulnerable with your friends?


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

I have an ideal partner. I split them up into multiple people. I am fully loved. I feel the love from my best friend from high school, Rayna, 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, but we chat about stupid stuff. 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 and I’m great at maintaining incredible, fulfilling, long-term twenty-year-plus friendships. I have lots of those. I value them a lot. I took my ideal mate and I split them up into multiple people.

I want to come back to a few ideas here. One of them is this idea of what makes a good friend.

I have some thoughts on that.

This is something that I’ve thought about and talked about. Some of the things that I think make a good friend have come up. I’m stealing this word from Darwyn, which is they’re energizing.

SOLO 8 | Dating Friends

It is not the Darwyn. You have a mutual friend named Darwyn, who is part of your origin story.

He uses the word, energizing, but you said intriguing and interesting. Those are all good words. I think you alluded to the 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 kinds of things. The other one is reliable. You actually give them a test, which is come to dim sum, to bro drinks, and to the DTLA Dinner Club. Do you have any other regular things?

It just dinners, hanging out. I make lots of dinners.

People show up. They say they’ll be there.

I have very little tolerance for flakes. It’s an LA thing for people to flake and people don’t understand the difference between flaking and canceling. They’re different things. Canceling is calling and saying, “Excuse X, I won’t come. Sorry, I don’t mean to waste your time.” Canceling within an hour, I consider flaking or hitting me up afterward and saying, “Sorry, I totally forgot.” True flaking 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 milder form of that is when someone who’s consistently late. It shows that they believe their time is more important.

The thing that’s important, I was very depressed in my mid-twenties. I saw 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 out, “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. When we meet at the club, you don’t want to know if I have something bad going on in my life. You’re not going to come to pick me up at the airport pre-Uber when that mattered.

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 with people I thoroughly enjoy, 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 a good one to the fourth. I added this one to the list. For the first three, I’ll take credit for the energizing term 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 and 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.” I think that’s a great way to think that they are your friends.

He is not wrong. I find that to be very truthful. I’m lucky enough that I have because I’m single. I don’t ever plan on getting married and I don’t ever plan on dating in the traditional sense. I don’t do “conventional, traditional type relationships” at all ever. I’ve never done it. I am able to maintain stronger long-term friendships. I have the bandwidth.

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 very 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, how you got to where both of you are. I see some similarities between the two of you, which is obviously you’re solo. You’re very focused on the community. In your bio, Lily, that you sent me, you use the word, “Ensembles,” which I think is a fun way to say community group team and this is central to who you are, Josh.

It is part of my personal identity.

In my experience too, I have always been more likely to be single than partnered up. I’ve had some family issues in life. I’ve always leaned very heavily on a group. Whenever I moved to a new place, I work 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 their origin story?

I’m very family-oriented and I know that 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 and I’m only 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 and there are a couple of times where they don’t crossover 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.” I’ve 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. I think that’s faith and spirituality. I’m not conventionally religious or a spiritual person, but I stay in the question of, “Is this my codependency?” I’m okay with that. I think there’s a real negative connotation to codependency.

I was in a relationship for a few years. There was a lot of codependency and a lot of growth over those few years. I’m grateful for it and almost all grateful I got out of it. I do appreciate the relationship. I would love to be in partnership, but I also am very 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 and Josh is a “forever” person.

It does sound like that. Josh is trying to say, “The cat’s feeling claustrophobic inside of the house.”

It helps us set the scene. We are sitting in Josh’s loft in Downtown LA, where he hosts his dinner club. This is weekly.

Starting in the summer, as soon as the weather gets a little bit nicer. 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 fifteen friends and fifteen strangers.

It’s an excellent way to get 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 totally random strangers, which is exciting. Fifteen people who have been before or who look super intriguing. People fill out a little questionnaire. I read every single application for the dinner club and mark people’s profiles, but everyone has an equal opportunity to get in. I spend several hours doing the seating chart so 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 were from different jobs.

You don’t put all the entertainment people together.

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

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

My origin story is super easy. I didn’t have a single friend until I was sixteen. I was bussed to school with kids that I didn’t like. There were no kids in my neighborhood. I was super alone and on my own. I was a latchkey kid. In junior high school, I discovered there was a film program. It is my first time to be in stage crew and I started to make friends. I went to Pacoima Junior High School in the hood. I was so 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 in like, “This is what I want to do. I’m going to get involved in the film.” The whole process from 13 to 18 was going to the movies with friends, organizing all of my friends, making movies and hanging out on film sets, 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. That’s an experience. I got a leg up and then I did more of that in college. As soon as I was out of college, it was continuous.

That supports my theory, not only my theory, but 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, also speak to what your strengths are, what your interests are, what you’re not good at, and challenge one another. That’s essential if you talk about the friendships that haven’t lasted very long in even those few descriptions you could go, “That’s where we fall apart. Someone didn’t show up for me or 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.

What are we missing?

[bctt tweet=”You have to be consistent about reaching out to the people that you find valuable. ” username=””]

Where you decided to put up this Chinese wall between your friends and your penis.

Is there a glory hole within the wall?

I’m not going to explain what a glory hole is but be careful googling it on your work computer. The other one is what is the Chinese wall? This goes back to, for example, magazines and newspapers, they have what they call a Chinese wall. I don’t even know the origin of it, but it’s basically the editorial decisions and the advertising decisions are completely separated for integrity.

Is it church versus state?

The ideas, it’s not going to stop you from writing a bad article about someone who might be buying advertising from you. Where 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. 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 that. How can you take advantage of having sex with a fifteen-year-old? 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.

I got me too.

It sounds like there was consent.

There was total consent.

Lily, thank you for arbitrating that.

I did it to be cool. I wanted my friends to think I was cool and I was trying super hard not to be gay. I started hooking up with dudes in college. I discovered the interwebs and 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 and it was always like that. It took until my mid to late-twenties to realize that it’s okay that I don’t. My shrink was like, “Why don’t you try it? There’s this dude who’s into you.” I was like, “Try dating him.” We dated for two weeks.

You don’t want him to stay over.

I didn’t want to. 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 and female? Gay or straight?


The top-level, he was fantastic. He was not one of those, “How does that make you feel?”

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

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

This is going to come up in a future episode because I’m going to have a guest who had a realization that a lot of therapists bring their own bias to the table, which is a partner life is a better life. 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, who has no opinion, who’s indifferent and realizes there might be a solo path for you, then suddenly his or her advice can change. We’ll give it a whirl to make sure that this is the right path for you.

That’s 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 is as close to being Christian as you can. She defines herself in a different way, but I’m not. We have great conversations about spirituality and religion.

One of my best buds, August, is a lifelong Catholic Christian.

Catholics have more guilt.

Whichever one has the big churches.

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

I love Mormons, though. They are nice and friendly. I’m not very religious. We have excellent conversations and he’s an incredible friend. His faith helps him be a better friend, whereas I’m totally a completely, hardcore atheist.

SOLO 8 | Dating Friends


Your values overlap. You might have received your values because you taught them in Sunday school. You might’ve 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’ve gotten them. I got mine from my family.

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

Lily, make sure you finish your thought about your friend who’s close to Christian.

She doesn’t celebrate anything pagan, but the idea that you can still be very 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. We can show up for each other and be like, “Do you want me to listen to? Do you want me to hold onto this information? Do you want me to give you advice? Do you need someone to vent on?” At some point, I deal with my therapist, “I’m going to give you the download. If you could reflect 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 and was like, “I want your perspective on this.”

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

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

I will tell you a quick therapy story. This came up in episode one, which is 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, it is a luxury. Therapy may not.

Who is your money person?

Money Amy.

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

Good news. She’s going to be an upcoming episode.

I’m very excited.

She’s going to get a lot of work at it. If you didn’t read episode one, I talked about a financial advisor being part of your team and have a particular type of financial advisor, which is a fee-based financial advisor. You pay them by the hour. You don’t pay them a percentage of your wealth. I have a very strong opinion about that.

I learned my lesson.

I have this great therapist back in Boulder. He’s The 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 was like, ‘I need to try to repair this, to 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 very somberly, anxious, a furrowed brow, “She’s not going to like that.” He said, “Be that as it may,” he said, “I’m not here to make your mother happy, I’m here to make you happy.” I started crying. I was like, “This person has my back 100%.” That is powerful. 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 wellbeing, 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, who changed my life.

You have to date a little bit.

If you find that best person on number one, great job, but 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 are giving them a favor too.

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

I want to jump back into sleeping with stranger’s 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. It’s not like 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 and doing this, your Dum Dums, that you have so affectionately referred to these guys.

It is not a negative term. God bless them for being such lovable, cuddly Dum Dums.

How does this go down?

I will turn my phone. I will turn on Grindr. It will start beeping. I will pick out what I want. They will show up. We will hook up. They will leave.

This is like Jetsons.

The whole thing happens within an hour.

I do this with Postmates and Dreams.

Is Postmates is for dick?

Yes, with a better selection. It is 100% and it costs no money. It’s so much more honest than a lot of straight people’s dating.

You’re talking about primal connection.

[bctt tweet=”Consistency and reciprocity help develop good friendships. ” username=””]

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 like, “We both know where this is going to.” I see such the drama, the dance that straight people do seem so exhausting.

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

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

He has helped me navigate language and identifying what I would like and all the things. What he says is, “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. Gay people hear consent and start talking, ‘What do you like? How do you like it? This and that.’ They put words to it even though they’re dealing with pretty much the same apparatus.”

It does help that we have our own equipment and we know what to do with it. It is very helpful. Also, there are certain things, for example, I’m exclusively a top. Plenty of people are exclusively bottoms or Bi or verse. 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 how it works.

For those reading, that’s my F.

You have to discuss these things in advance. There’s no shame around any of it. There’s so much shame I think around, unfortunately for women.

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

Americans especially.

We’re so repressed.

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 two sounded like a couple of Americans talking about non-monogamy or ethical non-monogamy.” I’m thinking to myself, “That’s what we are like in the United States. This is a revolutionary idea” In Berlin, it might be like, “Of course.” I think for the average person, they never thought of these words.

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

You’re on top of theirs.

For me, I think that 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, you can sift through the options and then you can communicate your preferences, exchange the pictures, 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 and that’s what I wanted to discuss.

I didn’t say only open.

It is easier, no doubt.

Tinder was a response. It was the heterosexual response to Grindr. Tinder came in after, as far as my awareness of it, if I’m not mistaken.

I know Grindr tried to do a male-female. The same company tried to do one for straight people and it failed.

It is because only men were there.

It didn’t work because women were worried about other women seeing them on this.

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.

How about the idea, the narrative around that?

I remember reading an article about it. Who knows what kind of things was based on data?

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

I think 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. The 10% that you don’t eliminate are there exactly for what you want. There’s Feeld, which is a whole new dating app for couples and threesomes and more, which is very heterosexual positive. There are lots of things you can choose from like heteroflexible, homoflexible, monogamous and non-monogamous. Feeld is a fantastic new app that’s in between of Grindr and Tinder. It’s for everybody. It only works in major cities where there are 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 is fun to see.

SOLO 8 | Dating Friends
Dating Friends: In your life, some people will move from acquaintances to friends and from friends to acquaintances and that’s okay.


Dating Friends: In your life, some people will move from acquaintances to friends and from friends to acquaintances and that’s okay.

That sounds like a sarcastic cool, but I’m genuinely saying cool. This is good for you. This is great.

When we were talking, I knew that I wanted to have you on here besides this is an interesting way to live your life, I want to highlight people like you because, 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. Some of it comes a little bit from the help of technology. This would’ve 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, but developing them so you can work on that while I do my talking.

I want to give you two a high compliment and the philosophy that you have, this solo philosophy of friendship has existed for a long time and was spearheaded by Epicurus, the Greek philosopher. He was a contemporary Plato but was much different. He was much more inclusive. While other philosophy schools were exclusives, Epicurus would take anyone who wanted to study and learn such as the poor prostitutes and so on, ahead of his time, as you might imagine. We know of Epicurean in terms of things that are delicious and delightful food, but that doesn’t give Epicurus his due. While Greek philosophers were interested in answering the question of what is a good life? What makes a good life? Epicurus was interested in what makes a happy life? What makes a pleasurable life? He attacked the assumptions and these are assumptions that exist still nowadays. The first one is he looked at partnerships and he saw not just the love and connection that exists in partnership, but the jealousy, the envy, the cheating, the misery that can happen within the partnership.

He concluded that a partnership is not the path to a happy life, but rather friendship is. Friendships rarely have jealousy as we’ve already talked about. Good friendships, real friendships and that they’re often uplifting. 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, pleasurable, and good. Working hard to earn money is a grind. This is Greek philosophers talking. The other one is that 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. People are talking about meditation and the value of meditation, 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 very clear as well as yours, Lily, I’ve seen it in a small dose. I got invited to a holiday party that Lily was hosting and she made her homemade ice cream. It was a delightful affair and really wonderful people. She did something that I thought was neat, which was one of her friends is in an improv group called The Resistance, which they improvised 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 didn’t know you were going to do it.

It was a revelation that happened about 24 hours ahead of time. If you’re still here at 8:00, we’re getting into a cab, Uber, Lyfts.

It was a great, very thoughtful party in terms of food and drink and introducing people. Lily was hustling. She was hustling so much that I suggested that we hire a bartender for her next.

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

Do you want to name that person?

There was not one person.

I realized that with the dinner club and with all of my events, I do multiple emails, progressively giving more information. My emails are also very clear now 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. As I said, Lily was part of it. This is a very small, intimate, six-person gathering where we spend a Sunday evening working through puzzles, problems that professional or personal that each person has and a lot of bonding. 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.

I’ve got 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.

It is the chefs that have been offended more.

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. That’s true. Ever since I started being firm on this, people stopped flaking.

We’ve talked about this idea of the importance of community and how much it can add value to your life. It can fuel you as an alternative to a traditional partnership in terms of developing. 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, though there’s still a probationary period. How do you do it?

I do 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, easy and consistent. 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, long-term, 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 a 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 and you have to be consistent about always having things that you do regularly that people can stop thinking about and fall into the habit of being involved in.

That makes it so much easier for people to build and develop friendships with you. I have lists of friends and I go down the list and I’m like, “I haven’t talked to that person in a while.” I’m a text message guy. I have no problem making conversations over a text message. I know a lot of people prefer phone calls or prefer in person. I prefer text messages and then in person. I want to text you for a bit, recatch up with you, and then at the end 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. I will send a car for you.

It is such a baller move.

It’s cheap. It seems like a baller move, but it costs an Uber X.

It’s hard to say no.

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

That’s great. How about you, Lily?

I lead with honesty and authenticity with myself. I’m not holding stuff 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 very good people person, people reader, behavior reader, and I haven’t given myself enough credit for that. It got me into trouble. Here I thought that I had a couple of great people in my life, including a boyfriend only to find out.

[bctt tweet=”When we love, how deep the heartbreak is is not necessarily within your control. ” username=””]

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

This came up when we first met.

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

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

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

Like heartbreak, when you fall in love with a person who was your friend, you have an amazing sexual connection with who’s also a dear friend that you’re adventure buddies with. Your lives intertwined and then your best friend from college, you yet to be the roommates, new thing and you’re the quad squad. You are hanging out all the time only to find out that he’s been talking trash about you to the girl he used to crap, who’s been a total asshole to your face behind your back. It’s undermining. That’s a chasm. That’s a heartbreak.

That’s rough.

That’s where the recovery from that has been a little bit rougher and what a beautiful opportunity to witness as I come up. 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 sometimes. Usually around politics, especially 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 and I’ll troll them sometimes. I like to watch their heads explode. I have 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 crap myself.

You’re 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 yes to me when I’m saying something outrageous. Fight with me a little bit. Call me on my BS.”

When you say troll, meaning you’re in person.

There’s no way they read someone’s face, only in person.

This talk is indeed interesting. There are all these dating advice columns and dating shows, but there isn’t anything like a friendship advice column or friendship advice. We hold these relationships up to this very high standard as this is such an important thing, albeit a difficult thing, and yet a lot of our happiness rests on the shoulder of our friends. I sometimes joke as like, “Someone meets someone, they disappear for a while, which may happen.”

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

Got it. Hold for laughter. That is brilliant.

I never heard that term before.

A trophy, that’s what you get. It’s the trophy.

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

They can hold it around. That’s 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’ve been in public before. That looks awful.

I know that he’s going to be moving to the Valley and I won’t. I miss him a lot and it makes me very sad. I know that my friendships, a lot of them, no matter how hard I work, they have an expiration date.

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

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

It changes things.

It does. 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 the fear that I have.

He sat down to have a conversation with you.


That’s a good friend.

You’re not going to lose me. I’m going to be your bro.

SOLO 8 | Dating Friends
Dating Friends: Consistency allows growth. It happens naturally and inevitably.

The sadness that you felt and you earlier 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.” At some point, that was an inconvenience for him to which is an indicator that we’re no longer that kind of friends. It’s not reciprocity. We are not in the same space at each other’s lives.

In your life, some people will move from acquaintances to friends and some people will move from friends or acquaintances and that’s okay. The thing about that and I had to understand that it is cool, is that I have had some incredible long-term friendships that are more like acquaintances. It doesn’t devalue any of the amazing times we had together. The incredible times we had for 10 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 share together. We were close. We were great, amazing friends. Maybe we can reminisce about that. Maybe we’re not that friends anymore, but it’s as important and it’s as 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 readers who are curious about that, if you want to stick around, we’ll get to that. I want to do an 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 and getting a positive response. I didn’t know what kind of response I would get and I’ve gotten a positive response largely. Compared to my other show, people are going crazy over this one. The other one is like throwing words into the ocean, but this one, people are leaning into. I’ve gotten a variety of different messages. Here are the three messages mostly that I’ve got. The first one is something along the lines of, “Thank you so much. This totally speaks to me.” I had someone say, “I’m crying.”

I think I might’ve been that person.

You were that person. I’m like, “I’m crying reading this.” I’m like, “Wow.” It’s easy to be like, “Maybe this is just me and maybe I’m a little too different.”

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

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

That’s what she said.

That’s what he said.

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

You had said that you were going to help build a community around this. I’m excited about 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 part of this.

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

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

That would be fun to do. There should be a place for people to be able to talk about these things. There is one resource that is available. It’s not mine. It’s largely spearheaded by Bella DePaulo, who was my second guest. She’s a scientist. There’s a Facebook group called the Community of Single People. It’s very clear that this is not for dating. You can do tons of that stuff. The last one and this one is funny, I’ve got not a lot of this. This has been the smallest of them is, “I love the show and reading it. I have to hide it from my wife or I was reading it in front of my boyfriend and 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 got a kick out of that idea.

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

I haven’t.

You are assuming that it would be coming from church people.

I’m biased. Something 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, that they’re very family-focused.

I found fascinating the stat that she gave about how most volunteer works was done by single people, except where it was within a church context.

You’ve got a good memory.

It’s good content.

That’s nice. I think this is a good update. I ask readers, please rate and review especially on iTunes. That’s the number one place where people consume podcasts. I’m trying to make new and noteworthy. My worry is this idea is buried in a sea of podcasts. Getting the word out will be good for this and be good for people like us. I’m going to experiment with the new thing. I did not prepare either of you for this. I’ve solicited some questions from readers. The first one is from Steve. He writes, “I’m an unmarried man and 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 the lady who currently 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 and as an actor. I am not a mom. I play one on TV. The expectation that I’m interested in your babies 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. 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, wherever that is, the sexual health aisle 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’s a pregnancy test for people who don’t want to be pregnant. The packaging, the color and the happy babies on one.

Does one cost more than the other one?

That I don’t know.

We got to do research.

[bctt tweet=”Our lives could evolve in different directions, but it doesn’t devalue how close your relationships were. ” username=””]

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 2 minutes. To circle back, I 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 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, and I’ve got 2 hours with you and then I’m off to my next thing? Is it, “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. Depending on your relationship, you got to find out, is this the time where it would help to be a part of the community? If you’re interested in meeting people, I would suggest hanging out with your married friends and/or your partnered 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?”

I think Steve should ask himself, “Does he know that?” I don’t know how close he is with this woman.

I don’t know either. It is a good friend.

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

It is a male friend.

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

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

Even to show up, give a high five, go home and do your next thing, it might be worth it for him to negotiate within himself and go with your gut. Where does your friend feel about this?

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

Give them a whole bunch of baby stuff 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. Of course, 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, but I love you and I will totally be there.”

I’m going to offer something that splits the difference between both of you. Both of you basically say go.

He says it’s a good friend. He also didn’t say whether he has $400 tickets to book a Mormon or something. It’s not like he didn’t say what the other thing is. I’m assuming the other thing is missable.

It’s something he would rather do. To me, I feel like building on this idea of what makes a good friend and you’re on 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. 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.” I think about my best friends, what they’ll say is, “I need you there.” They’re like, “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 go do X another time.” I feel like a strong friendship, whether the fact that you 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. I think the doctor has the correct answer here.

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

I think you found it.

My first reaction was, “Don’t go.”

There is 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 that you love doing it. 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 and ten people, the consistency of every Monday Jane does X. 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. 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, but doing one thing, pick one thing and do it every single week at exactly the same time and day or every other week at the very minimum. Once a month doesn’t count. It has to be every week or every other week. Even if only one person shows up, some days, twenty people will show up. That’s how you build that consistent community. It’s the easiest, simplest way to get started on that. I highly recommend you.

That is a strong answer.

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

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’s the easier route sometimes too.

Not everyone has a way to stretch yourself.

If you moved, I’m going to relocate to Minneapolis and I’m looking at what’s a meetup around that. I have some family up there, but also what else would I be interested in?

It’s being at the same bar every Friday at 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 between 5:00 to 8:00.


SOLO 8 | Dating Friends

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, but it can be a coffee shop. It can be a riding group. It can be anything.

I agree. I do want to give an added tip to this, which is name it well. Naming things is important. Bro drinks sound more appealing and you’re like, “I got to find out what bro drinks are.”

Can I also offer another would be finding a nonprofit, someplace to volunteer? I think that also gets you into the community in the service of others. It gets you out of whatever your stuff is.

I’ve got out of depression because of James Altucher, maybe his book. 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. Let me help you.”

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 was what many people do.” How do you find your community? What I wanted to say was look at any rom-com in the ‘80s and ‘90s. There’s always someone leaving their apartment, throwing a coin to the newspaper, to the newsstand, grabbing your thing, grabbing their coffee. That’s consistency. That’s exactly what I’m talking about.

Don’t get discouraged if you do it for a month, every single week and you’re there with one person. Consistency allows for 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, but stretching yourself and working to organize 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. I have to populate it.” It changes your orientation in life. For example, you’re at a coffee shop and you’re on the lookout for someone cute, but when you have a community event, 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 is you’ve got a light inside and it is up to you to make sure that you are fueling it. You want to share that with the world, but that’s not going to come when you’re in your own space like, “I’m looking for my number one.” When you’re pursuing something, as opposed to showing up and being curious as to your authentic self.

As a single person, I’ve got to tell you, one of my least favorite things is, “You’ll find it as soon as you’re not looking for it.” There are so many times I want to slap a person.

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

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

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

That’s fantastic. Thank you, Steve, Jane, Josh and Lily, for your participation.

This is super fun.

For a little bonus material, Josh made us old fashions.

It’s to lube us up a little bit for Valentine’s Day.

My old-fashioned feels very fresh in my mouth.

It’s delicious. I have some good whiskey.

Old by name only.

As solos, what do you do on Valentine’s Day?

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

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

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

That’s what you should do on any Wednesday.

Always crap first, you can eat all the foods.

That’s totally a Dan Savage thing.

I agree with it.

Anybody who’s ever dealt with bloating or IBS, you’re going to be so much better on an empty stomach.

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

I’m going to have to say something about that. Everyone thinks I get laid after dinner club. I have never gotten laid. I’m exhausted and full and the place is a mess. The chefs are hanging out, finally. We were chatting and cleaning up and everyone’s like, “Dinner club is so good for getting laid.” I’m like, “I’ve never got laid after dinner. I just come to a dinner club.”

[bctt tweet=”You’ve got a light inside and it is up to you to make sure that you are fueling it. ” username=””]

Maybe if I had a dinner club of just oysters for solos, that’s myopic.

I’m afraid that old fashions are kicking in.

I got to lead with something. I’m very lucky. My birthday is August 14th, which is exactly six months before and/or after, depending on your perspective of 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.

Do you send Valentine’s Day cards?

I had done that before but my dad and my brother laughed hysterically and they were like, “You sent us a warning.” By the way, 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. It’s fun, in a comedic sense, to subscribe to the notion of gifts. I’m very lucky because my family disbanded with holidays on the actual days. 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 roses and plan the overpriced dinner at the restaurant you can’t get into, 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 Years.

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

Also, I stressed the crap 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 and said, “In a world full of daisies, you’re my rose.” I was like, “Dad, that’s amazing.”

It’s a pretty baller move, but what do you do as a solo person? What are you doing on your half birthday girl?

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

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

I find myself opening my arms to the people who are upset about not being coupled up and going, “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. What is going on that night is the lovely movement away from Valentine’s Day as a Hallmark holiday does at least allow for a trivia night and stupid things to be happening that night.

Going to comedy shows.

Comedy shows is good every day, especially if you live in one of the cities that has great comedies like New York, Chicago, Los Angeles.

Boston, Washington, Atlanta and Denver.

Nashville, lots of cities have great comedy. A comedy show is a win every time, even if they suck.

You went out, you got out, 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 and the mediocre is the only loser in a comedy. If it’s going to be bad, you want to be rolling.

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

You’re the story for everyone else sitting around.

For you, driving home, not a good night. When did I ask you if you loved me and you didn’t say yes, why that happens?

For Valentine’s Day, I don’t do anything. I just want to sit at home, watch some movies, skip right past the Hulu Valentine’s Day Channel and hang out. If there’s a couple of friends around, great. If we have a couple of drinks, great. I think the key for solo people is not to feel pressure or resentment or feel bad about the way you’ve chosen to live your life just because there’s an entire industry making $1 billion that day. Making everyone feel like they’ve got to feel bad if they didn’t get the perfect gift, have the perfect person, get those dozen overpriced roses, or make that reservation at that overpriced restaurant, which has a special menu, which is three times the normal servings.

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

The first Sunday after New Year’s is the biggest online dating day of the year. There’s a 30% increase in online dating on that day. It is fascinating. 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 sort of familial pressure and then the other one is Valentine’s Day is 5 to 6 weeks away.

Are people planning for that? Is that much pressure? That makes me so sad.

Do you know what a few corners is around? Your death. What are you going to let pressure you into?

What I think is interesting is Josh, you led with, “I feel bad for people.” There’s this interesting dynamic, which is the people who win on Valentine’s Day are happy couples with wealth. If you’re wealthy and a happy couple, it’s a great day. It’s a chance to reflect and it’s a chance to celebrate. It truly is something. Sometimes you take things for granted.

SOLO 8 | Dating Friends


Today is the day that you two appreciate each other. You’re wealthy enough to hire a babysitter and go out to a nice restaurant and get the nice roses and the ring.

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

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

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’ve seen lots of not working ones.

We should celebrate the people who do it really well.

We also celebrate the relationships that got us to the place that we are consciously solo. 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 unhappy couples. I have some sympathy for the unhappy couples because there’s a lot of pressure. Sometimes external forces do us a favor and maybe if it is the case that 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. 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 to the 13th and then suddenly on the 14th, you feel like your life is lacking something that’s there. I feel bad for those people.

I’ve been there.

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

Every store already has Valentine’s stuff up.

There’s nothing going on between now and then.

There is stuff going on, President’s Day, Martin Luther King Jr.

What do you sell for that holiday? We don’t commercialize that holiday.

Sorry, Hallmark. You can 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. The people like us in the room who are unpartnered and comfortable.

For us, isn’t it just any other day?

That’s what I was saying. 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.

That’s a good idea.

Maybe I do a yoga class or I go for a walk.

Self-love the crap out of yourself.

I might have a quiet night. I might work on one of my secret projects. This is a night that I can be free in terms of like, “I’m going to celebrate the fact that I’m living a good life and I’m going to stay away from the restaurants.” I do buy flowers for myself every week as we should. Josh does too. He’s got some orchids.

I buy lilies for myself because they smell amazing.

I like orchids. They’re my flowers. I get orchids.

I like tulips. 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 a flower shop.

The best day to buy flowers, the day after Valentine’s Day.

It is the best day to buy Halloween candy too. The best day to buy ornaments is the day after Christmas.

Josh, you answered the question of 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 crap about what holiday it is. I’ve been literally working. I became a server in the last years. I do that. I’ll cater. I was working at Universal Studios as a tour guide. I’m also still acting like all the jobs in the world. I am hustling. This year, 2020, will be the first time that I am without a job that I’m aware of and 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 and I would be more than happy to be invited into whatever they’re doing because we play a pretty good Tapple.

Maybe you could play this episode for them. Maybe she’s not down with that.

They know everything about me.

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

Lily, anything you want to finish with?

I am glad to be here in the moment with you, guys. Thank you for this.

This is great fun. Thanks so much.


Important Links


About Josh Gray-Emmer

SOLO 8 | Dating Friends

Josh 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 dinner party focused on building community and not profit.



About Lily Rains

SOLO 8 | Dating 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.