How To Go On A Date

Solo 41 | How To Date


Are you good at going on dates? In this episode, Peter McGraw brings together two previous Solo guests—dating coach, Daliya Karnofsky, and a solo friend, Jill Cohen—to talk about “how to go on a date.” The guests present helpful advice, from the obvious, “Brush your teeth,” to the critical, “Approach your dates with a sense of adventure and authenticity.” Note: The group tackles the topic largely from the perspective of traditional stereotyped gender roles between men and women. Peter will return to the topic later with guests who can talk about dating outside of well-known stereotypes.

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Listen to Episode #41 here


How To Go On A Date

This is an entertaining episode that brings together two previous guests to talk about how to go on a date. Note that we approached the conversation largely from the perspective of traditional stereotype gender roles between men and women. I’m going to return later with guests who can talk about the topic outside of some of these stereotypes. My guests present a lot of helpful advice from the obvious brush your teeth to the critical approach your dates with a sense of adventure and authenticity. As you’ll read, the three of us are good at dating and speak with confidence, but I recognize that dating can be difficult. I hope the information will help you make the experience a little more pleasant, perhaps even fun.

One way to do that is to stop thinking about dating as finding a life partner and a future parent for your children. The person you’re meeting could become a friend, business partner, or may fix you up with someone else. This should be heartening for you, the solo reader, who may not have the goal of finding the one anyways. One announcement before we begin, I’ve launched a Listener Message Board on the Solo page at PeterMcgraw.org. There will be general topics about being single and living a remarkable life. There will also be topic threads for each episode including this one. If you want to help build the community and have a discussion about what you’re hearing, go to the Solo page on PeterMcgraw.org and please contribute. I hope you enjoy this episode. Let’s get started.

Our guest cohost is Jill Cohen. Jill grew up in Miami, attended Emory University, received a Master’s in English from the University of Colorado and resided in Boulder for many years, which is where I met her. As a traveling ER nurse, she’s worked in Colorado, Wyoming, California, Florida and Australia. She joins us now from Truckee, California, where she started working as a nurse for a virtual medical team. You may recognize her as a guest on episode ten, What Makes A Life Remarkable. Welcome, Jill.

Thank you.

Our guest is Daliya Karnofsky. Daliya is a comedian performer and dating coach. She works privately with clients on everything from online dating profiles to breaking up and moving on. She hosts the podcast, Not Your Therapist, which is one-on-one dating coaching for guests, both anonymous and not. She’s the Co-creator and Co-host of the live show, All My Single Friends, which is a half-comedy show, half-live dating app in Los Angeles. She also returns from being featured in episode sixteen, Making Single Friends and More, where she critiqued Jill and my dating profiles. Welcome back, Daliya.

Thank you for having me.

I might have misspoken having Jill as a guest co-host in some ways. She’s also frankly a guest here but we are here to talk about how to go on a date from deciding, planning, prep, actual meeting and follow-up. We’re going to go through each of these steps. I’m going to be throwing some questions your way that’s submitted by the audience. In particular, I want to thank Kim, Kevin and Jane who sent me about 100 questions. Deciding this might be the most important topic.

Can you clarify what you mean by deciding to go on a date?

Do I want to ask this person? Do I want to say yes to a request for a date?

I’m going to have to disagree with you right off the bat.

That’s why you’re on. Tell me why.

Dating is a numbers game and I don’t know how much work you’re doing in your head before deciding to go on one date, but it’s one date. Just go and ask. You’ll find out really quick if it’s not the person for you but there’s nothing to be gained by staying home. It’s two hours of your life. You don’t have to go for the whole day. You don’t have to sign up for a week, but going on one day, that’s not a big decision.

I would say there’s another category. It’s deciding to engage in the dating world. There’s the big category and then the small category of individual dates. On the one hand, Daliya, I totally agree with you. You’re never going to know unless you go. On the other hand though, I had an empowering experience. I have a story for everything so I’ll try to keep them short. There was a guy who I matched with on Bumble. We talked on the phone, we were going to go on a date that night. He was a physician and somehow, we were talking about our work because I’m a nurse, he’s a doctor.

He proceeded to tell me a story about how he yelled at a tech who was working for him because they didn’t do something right. He started laughing and he said, “Isn’t that funny? Isn’t that hilarious?” As the person who sometimes gets yelled at, because I’m the nurse and as a human being with a modicum come of decency and kindness, my response was, “I don’t think it’s funny at all.” It was very empowering at that moment for me after initially saying, “Sure. Let’s go out,” to then say, “I don’t think so. I’m going to skip it. Thanks for asking.” On one hand, go for it, try it, and meet people you never know. On the other hand, if you get a bad feeling about something, it’s your life, your choice. You don’t have to go out with anybody.

I agree with what I said but I do think and I know we’re ignoring the COVID dating. One interesting thing that’s come out of it is people doing these FaceTime dates or phone calls first. They don’t have to go out for a whole evening because that’s a much bigger commitment now, health-wise and everything. I used to always recommend to my clients, do a phone call or a FaceTime before you go on the date and I let that out because to me, that qualifies as a date. That’s your first meeting in a sense. I’m fine with if you talk to someone on the phone and you’re like, “Definitely not.” You should follow your instincts and you shouldn’t go.

We’re basically saying the same thing.

What about red flags omissions? It creates some uncertainty. I get this idea of like, “Do it. Be adventurous. You don’t know until you try.” There are situations where there are some things in a bio or something that comes up in a conversation that starts to give you pause, missing photos, or photos only from one particular angle that makes someone seem tremendously appealing, that kind of stuff. Making those decisions can matter. As soon as you walk into a room and you go, “This is not the right fit for me.”

That’s where the preliminary call or FaceTime is great. It prevents you from having to walk into that room. For people who are a little more cautious, busy, or whatever it is, they can do that. Especially if it’s a photo concerned, FaceTime is great for that. If it’s a phone call, you can always ask questions about those things that gave you pause, you can prod a little bit, and get some more information. You’ll see a team with me which is that I err on the positive side of things. Rather than looking for red flags, I encourage people to look for green flags because we are conditioned to look for red flags. I also think the term red flag has gotten totally overused and blown out of proportion.

To me, the red flag is yes. Someone who’s bragging about yelling at someone who works for them. A red flag would be alcohol problem, bad temper, misogynistic, something along those lines but something like, “Yes, roommates,” or, “He likes this band that I don’t.” People love to be like, “That’s a red flag.” I’m like, “That is not a red flag.” Let’s separate those two things because we all know couples get together all the time who have nothing in common, who disagree about everything, or who had different musical tastes. There’s a point with online dating where we get too micro and we start looking at all those things, looking for if they’re a good person. Other than that, I don’t consider things a red flag.

I agree with that. My particular one is someone who likes live music. I understand why people like live music. I’m not excited to go to see live music, but I should not treat that as a reason to not see someone. You can manage the live music preference.

They can go, that can be the thing they do with their friends. They do it by themselves. That’s a beautiful thing to have separate interests. It’s a beautiful thing to have things that are something you do on your own. Something like that, I would not consider a reason not to date.

I totally agree with that. I do Lindy Hop dance, which is a vintage era swing dance. It’s a niche hobby for sure. I have rarely dated someone who does Lindy Hop but it has been great. There was one guy I dated who would come to a performance if I was having a performance and that was wonderful. It was great for our relationship because then he’d see me up there doing my thing. It was something that he could be proud of me for and something I could show him. He did other stuff that wasn’t into, but I was supportive of him. It was a nice thing for us to have our separate interests. The other thing you said, Daliya, that was great was that you can ask about certain things.

If you see something, don’t necessarily write the person off because sometimes people make typos. It could be as simple as that. It was hilarious. I became friends with the guy who I met on Bumble. We didn’t wind up dating but he had on one of his fill-in-the-blank things something to the effect of like, “Have and want more for kids.” I was like, “That doesn’t seem congruent with anything else in his profile but let me ask him.” I did. On one of my text messages, I said, “Can I ask you something about your profile?” He wrote me back. He said, “I must’ve been drunk when I filled this out, joking around. I don’t have kids.” I was like, “Good, we can proceed then.”

That’s a great example. People do that so much. It’s also like, most people are not good at writing profiles and not good at picking pictures. That’s not a natural skill that normal people are good at. That’s something someone who’s good at that is not necessarily someone you would want to date too, except for me. It’s a great point, if you see something you’re like, “That’s weird.” Why would you not give them the benefit of the doubt and ask the question?

I’m going to say I like Jill’s point about do you even want to be dating? This is all predicated on a desire. Solo is not about sex and dating although the opportunities as a solo are often greater for new partners and so on. I came across this article by Shani Silver who has a podcast called A Single Serving Podcast. She wrote this for Medium. She talked about the person who hates to date and the challenges that they find dating as she described it. This hookup culture where people have mismatched preferences, some people are looking to date, and other people are looking to fool around. As she said, “I freed myself from dating as a mandatory chore is one of the greatest gifts I’ve ever given myself, which is why I fight hard to help others to do the same. To be able to recognize what is it that you want to do because singles tend to date or have the opportunity doesn’t mean it might be right for you.” This conversation is predicated on a desire to be in the game, so to speak.

One of the first things I talk about with my clients is do you want to date? Do you want to find a partner? Let’s figure out what you want because it’s an assumption that people don’t want to be single. If they are single, they’re trying not to be. I don’t think that’s true at all. There are plenty of people who thrive on short-term relationships, other types of relationships, and do not need to be in a long-term relationship.

Let’s move on to some more important ones, perhaps these equally unimportant ones, the planning. How to go about planning? This encompasses how to ask the medium and then also the choice of what to do.

Are we talking about when you meet someone on the apps?

Let’s be a little bit apps focused but let’s also imagine it’s a normal world and that you might be meeting people in real life, as limited as that might be at the moment. It won’t always be like this so let’s make this podcast worthwhile for years.

I’m going to clarify as Daliya did with deciding. Planning, do you mean planning a date like where to go, what to do?

Yes. I’m assuming it’s somewhat a joint decision. There may be someone initiates, but it’s always a bit of a negotiation.

There’s a lot of different ways that can happen when it comes to the apps and you may disagree with me on this because I know you like to get a lot of information but I generally don’t app chat conversations to go on for too long without getting to the, “Should we grab coffee? Should we grab a drink? Would you like to meet in person?” Nowadays would be like, “Should we do a video chat?” There’s only so much you can learn and it builds a false sense of intimacy when you’re chatting and chatting and asking all these questions. Everyone is so safe behind their screens and what you want to do because you might hop on the phone and know right away this is not the person for you. You couldn’t have known that without that information. The sooner you can level it up to either a phone call, FaceTime, or let’s exchange numbers and go get a drink, the better.

I agree too because you can also lose a lot of momentum if you text too much.

Let’s assume you get to that point where you chat on the phone, you do a FaceTiming, and you’d to meet this person in person. The planning those moments, what comes to mind? Stories, experience, ideas. This is an audience’s question. “Do I pick or let her?” This is a guy who’s writing this. This is someone getting back in the game. I read that women like when you pick a spot, but it seems weird to me if we go somewhere too near her, that kind of thing.

The best thing to do in these situations is to ask and say, “I’m happy to pick a spot in your neighborhood, but if you prefer, we can do a midpoint. What food are you into? What atmosphere are you looking for?” You can do the legwork, which is nice for the guy to do because generally speaking, the women have a lot more getting ready to do and a lot more in terms of their safety, a lot more at risk. It’s nice that the man puts in the legwork at the beginning. I’m speaking about traditional stereotype gender roles when I say this, but someone should put in a little more legwork in the beginning. Generally speaking, it’s best to do a drink or coffee, keep it to two hours, don’t do dinner. I’m not that, even that into an activity for the first date. The first day, you keep it short and sweet where you can look at the person and see them. The next day is great to do an activity or something where you got to be a little bit freer in your bodies and relate on a different level. Keep it simple for the first one. It’s nice of you can ask the person what they like and where they’d like to go and then take it from there.

Axe throwing is day two.

It’s funny when this has evolved. Earlier in my dating life in 2000, we didn’t know that it’s a good idea to go get coffee as opposed to planning some big thing for the first date. There was one date I went on that we decided to go do karaoke for the first date, which is such a bad idea for a first date that it wound up being amazing. We had the best time and I look back on it. Who would do this now for a first date? It’s become such a rule for a good reason to make the first date more of, do you want a second date kind of thing? You never know.

If you met that person for coffee, you would have had a good time. That’s the way I think. This idea of keeping it to an hour to keep the costs low having an escape plan is not because you don’t have to be worried about missing an opportunity with someone you click with. A lot of my audience questions use the word, vibe, “That you vibe with.” It’s to avoid the situation where you don’t anti-vibe with the person. That’s where this advice originates from is the fact that it’s often hard to make a match. Most of the time, it’s not going to be let’s go ax-throwing next time or what’s available.

It’s always also a good plan to plan something for yourself afterward whether that’s meeting up with a friend or having a fun plan to stop at your favorite bookstore that happens to be by the bar. I went to acting school and they used to tell us after you go to an audition, no matter how it goes, get yourself a treat afterward because you want to build up that muscle of like, “Rejection is hard. It’s hard to be an actor and put yourself out there, but you’re going to get a treat every time, good or bad.” With dating, whatever that is and keep it short too is a great idea.

A lot of times, people will be like, “I had the best first date. It went on for seven hours. We went here, there. It was the best day of my life.” They never hear from the person again or then their next date is disappointing with that person. You want to leave both of you wanting more. You want to seem like if something else to do. Not in a fake way, but it’s like, “I don’t have six hours to give a person I just met.” It’s a lovely, romantic idea but you’ll get a little burnt out and you’ll feel weird about it after so if you’re like, “I’m going to give myself something to do after so I have to go.” You’re setting yourself up for a better experience.

Do we all agree?

I think so, yes.


This is an audience question that asks, “Is it okay for a woman to initiate asking out?” This is a little bit more of the traditional gender roles. My experience has shown that a guy likes it and he’ll try to see you.

It’s context-dependent so do what you feel. I’m not going to tell you not to. There’s definitely something hot about asking a guy out that you meet in person. This is rather old-fashioned and controversial of me to say. When you ask a guy out, you’re already showing him that he doesn’t have to do the work. A lot of times, I get people who are like, “I’m always with guys that I ended up taking care of. I mother them, I do everything. I do emotional work. I make the plans.” If you don’t want to attract that, then you have to sit on your heels a little bit and let them do the work first time you’re setting up that dynamic.

That advice is largely good, but what it overlooks is a guy who doesn’t need taking care of, who has a lot happening, and does well with women. What I mean is you can stand out as different for a guy who’s a bit progressive who is often like it would be an appealing date in that sense. I agree with you. If the guy is a bit of a loser and he’s on top of things that I agree, you’re going to drag him around, he’s not going to be a good date and he’s not going to be anything more if that’s going to develop but for a small group of guys who are a little bit more appealing, it can have a beneficial effect.

I would totally agree. If there’s a guy who’s career-driven, not thinking about dating, or whatever it is, I would never say don’t do it but I would say if you’ve noticed that that’s your pattern and you’re always ending up with people that you end up doing all the work. There’s a reason and you want to see if you can get someone to put in the work for you. It’s also fine if you ask them out the first time and then they pick up after that. I’m fine with that. You should be paying attention to how much effort is being put in on both sides is what I’m saying.

I see it a lot. I see it with friends and I’ve seen it in my personal life where sometimes you’re a little too defensive. You can miss an opportunity with an appealing partner.

What do you mean by defensive?

What happens a lot of times, especially if you’re an appealing person yourself is you get a lot of inbound offers. There’s a lot of texts, likes, swipe rights, phone number asking, and all those kinds of things. There’s a tendency to put a wall up, to play a lot of defense, and to be like, “You need to impress me. You need to stand out.” That makes sense for the 95% of those inbound things. The issue is the 5% that you want is often someone who’s equally appealing on the male side of things. We’re talking traditional and we should be careful about that because this works. It doesn’t matter if you’re heterosexual or homosexual. It’s the idea of people who are most interesting. It’s the 80/20 Rule, 20% of the people get 80% of the attention. I would hate for someone that’s like, “That guy seems great.” He’s a little slow, unresponsive, and stick with your normal game plan which makes him work for it. I was like, “I’m sorry. He may not work for it because he may not need to as much.”

Here’s what I think. You have to know yourself and be yourself. If you’re the kind of person who likes to extend yourself to somebody, reach for someone, and you don’t mind doing that, that’s okay. If you’re not the kind of person who hangs back and pretends not to be interested then don’t be that person as a strategy to get a date. However, I will say, think about what you want. Do you want someone who’s going to reach for you? Do you want someone who’s going to extend himself or herself towards you? If you are constantly reaching and always doing the work, you don’t leave any space for someone to come towards you. There’s a little bit of a balancing act there where you have to balance this. Being yourself and being truly who you are, but growing into another part of yourself that let someone come to you because that’s joyful, fulfilling, and satisfying. That’s something that other people like to do. If you don’t give them the space to do that, then you don’t give them the space to do. Those are my thoughts on that and as Daliya said, “It’s okay, ask a guy out first.” Notice, is he reciprocating? Is that important to me? Do I want that? If you do, you do have to hang back a little bit.

We can move on, I’m not far away from you two on this. I wouldn’t say but I think there are problems with traditional gender roles.

I want to talk about a concept that I love that’s from a long time ago about dropping the hanky which is you don’t have to ask them out, but you can let them know that you’re interested. That can be what the ask out is. It’s like, “We should go out sometime, let me know.” You’ve done your work, you let them know. If they can’t pick up the hanky after that then we’re moving on. That’s a little bit of a compromise move.

Peter, I totally agree with you. These days I never want to pretend like I don’t care and pretend I’m not interested. If I’m interested in a guy, there are ways I’ll let him know, but I want to make sure I don’t bark up someone’s tree when they’re not available, not interested, not making any moves in my direction either. I’m not saying ladies don’t do it. I’m talking in traditional gender roles here. This would be for anybody. I’m not saying don’t do it. I would say, “Go for it. Give it a try.” If you want someone to extend themselves back to you then you have to give them that space as well.

Any other ideas in terms of planning? If I could summarize for a moment, it’s this idea of get there, meet the person but don’t over-commit time and money to this. You have a lot going on. Spend that hour or two hours over a drink, coffee, walk, something that you can assess, and then save the excitement for later times.

There’s plenty of time.

Let’s say you meet someone and there’s mutual interest attraction, and so on. For the two of you, is dinner fine the next time? Is it okay to go a little bit bigger, special, fun, have some adventure?

Activity is great for a second time and activity doesn’t have to mean like karaoke or wild bungee jumping because if you go straight to dinner, you spent two hours sitting across from each other. Now you’re going to spend three hours sitting across from each other. Even if you go to a movie and then get a drink after so you have the movie to talk about. It’s something to change it up a little. It’s a lot of pressure, especially if you had a good first day which I’m assuming you had a pretty good one if you’re going on a second date. You’re already putting pressure on that second day to think second dates are the hardest because then we have this expectation, but we’re not yet comfortable and we’re still sussing this person out.

The second day, if you give yourself something to do that might still require a little bit of physicality, or take you both out of your comfort zone a little. I’m watching this dating show on Netflix where on their second date they went rollerblading and they were both falling down all over the place. They were catching each other, helping each other, and laughing. You can’t help but create this vibe with another person when you go through this experience together.

When someone breaks their arm, you get to see how the other person is in crisis in the ER.

I am 6’5”. I will not go on roller skating or skating dates ever.

Your gravity is way too high.

It’s the only risk, little reward there. Prepping for it. I’m thinking of the actual preparation. You’ve set the date, it’s agreed upon, and then there’s some period of time before it happens. Anything as you think about preparing for it. I have some topics and things, but I want to get your off-the-cuff reactions.

Number one is to make sure you have some time before the date to decompress and let go of wherever you’re coming from. A lot of times, people cram in a date right after work. Give yourself at least twenty minutes. You can sit in your car, you can walk around the block, change your clothes, change your feeling. You want it to feel fine, not a chore, different from work, or something else that you did that day, or you’re not getting lunch with a friend. Play your favorite music, have half a glass of wine, don’t go overboard, or pick your favorite outfit. I used to have the same outfit that I would wear on every single first date because I knew it looked good, I didn’t have to worry about it. It was like, “Time for the show. I’m putting on my costume.” It could be in a certain headspace. I was like, “It’s time.”

What was the outfit?

It was a little floofy mini skirt and a little crop top, not too short but long-sleeved crop tops. You show a tiny bit of midriff to be like, “Hello, I’m here.” A boot because I’m short, a little heel. It was flirty, fun, feminine. It wasn’t how I dressed in my every day. It wasn’t like jeans that I wear out with my friends. It was like I’m putting in the effort for you which is important to show someone. I care about it. I’m in a good mood and I would make sure I had enough time to decompress and get in a good head space because you don’t want to bring all that.

I bet you have a lot of second dates, Daliya.

This is Greenlight Daliya that we’re talking right here.

I was going on six dates a week at one point. I was having a blast.

What was that core outfit?

I still have that shirt as a memento. It’s worn out. I can’t even wear it but I still have it.

You got to frame it.

Daliya’s Dating Hall of Fame. The physical and the dress are good notes. Daliya, I have a friend who never drives to a date. He always takes Uber. He’s in LA, and besides the fact that he might have a drink or two, he wants to arrive relaxed. When you’re a passenger in an Uber, it’s typically more relaxing than driving yourself, finding parking, and all of those things. That creates the right headspace.

That’s a perfect segue because it eliminates things that will make you feel self-conscious or uncomfortable. For example, if having hairy legs makes you uncomfortable, make sure you’ve taken care of that before you go. Get rid of the unsightly hair so that when you’re in the company of that person, you feel confident. An outfit that you know you look nice in, a grooming thing, or whatever that you know you’re not going to feel insecure, unattractive, or lacking confidence. Take care of that before you go so that you can go and enjoy the date.

I’ll give you one. I like to get to wherever we’re going early and I stake out good seats.

Speaking of typical gender roles, I love when the man does that because it shows that he cares, he’s putting the effort in, and then the woman gets to have her arrival or whoever it is gets to have their arrival. I used to text my dates and I would say something like, “Can we meet outside the bar because I hate that awkward moment of walking in and looking for you.” Even though I’m an outgoing person, I hated that moment. I didn’t want them to see me and me not to see them so I would make them meet me outside. Most of the time, I would do that but not all the time. That’s something to consider too. I also tell people to make sure you’ve had a snack.

No one wants to show up hungry, tired, and you’re going to get drunk really quick if you have a drink on an empty stomach, brush your teeth, that’s a big one. People don’t think of that. You’ve got to do it, brush them. It’s basic but make sure you’re in your best possible headspace and you’re feeling good. Another tip from acting school is they used to always say, “Don’t go on an audition in an outfit you’ve never worn before.” Not a new dress even though you’re like, “This is fun.” You don’t know that dress could fall off of you. You don’t know with new clothes what’s going to or new shoes, those hurt. Go with the tried and true.

The reason I said about the early in the seating is that you can make it easier to talk, you’re dealing with sound, and lading. With a face like this, I need lip as well as possible. I care about aesthetics. That’s one of the things. I want to ask a question. We’ve been dancing around this a little bit with how you get there, what you wear, the fact that you’ve flossed, but the right mindset as you’re preparing. I’ll offer one which is in a form of a question but to be a little bit flirty in the sense of you’ve said it and then some people choose, “It’s set, I’ll be quiet,” versus be a little playful and have some fun before, “Set a little bit of expectation, this is going to be a good time.” The other one is what’s the mindset walking into this? Do you two think someone should have?

I think about this a lot when it comes to dating and I don’t love strategy necessarily with dating because I feel like if you go with a recipe or a strategy, there are good things to do that are going to help you put your best foot forward. That’s part of you, your best foot forward but I also think you don’t want to attract something different that resonates with you or is right for you by putting on an act. I don’t think we’re talking about it as an act, I said that for lack of a better term.

The worry is the pickup-artist-type stuff is distasteful, I will say.

On the other side of it is the rules-type stuff for women. You could attract the wrong person by pretending it’s you.

Am I going to attract the wrong person by being a little flirty?

No. Maybe I misunderstood the question. If flirty isn’t who you are. If it’s uncomfortable for you and you like to talk about sports, science, or the bug that you saw on the sidewalk before you walked in, do that. The girl sitting across from you might be turned off by that, but then maybe she’s not your girl. It’s the girl who goes, “I saw that bug too. Wasn’t it weird?” You start talking about a bug and the next thing you know, you connected about something and it’s genuine. I don’t know why I thought of a bug on the sidewalk. I’ve never talked to anybody about a bug on the sidewalk, but if that’s what woke you up at that moment and that’s what was on your mind, why not say it because how the person you’re with reacts to that could be telling about your connection or your potential connection.

The mindset thing is very much that. It’s about being authentic. What I think of when I hear mindset is a lot of people go into a date wanting to figure out right away, “Is this my person? Are we going to be in a relationship? Are you the one?” That’s a huge disservice to yourself. You want to go in to learn about a new person, to get curious, to ask them questions about what you’re interested in, what made you go on the date with them. Assume they are not your person or you’re going to meet an interesting person, before the days of COVID, you might get a make out of that. It was a huge proponent of that. Assume you’re going to learn about a person, it’s important to note that you could meet a person, they could become your friend or business partner. They could not be right for you but three years from now, they could know the person that you’re supposed to date.

If you have a good time with them, but it’s not a romantic connection, you’re kind, curious and stay open, they’ll be like, “You should meet my best friend.” I’ve heard of that happening many times. You do yourself such a disservice if you get there and you’re like, “He’s not for me. I’m shut down and I’m waiting to get out of here.” The people who go in and are like, “Are you looking for a relationship?” Do you have to talk about that on the first date? That’s not the first date like, “We’ll all figure out what we’re looking for.” They certainly don’t know what they’re looking for. Get curious, talk about a bug on the sidewalk, I always say start in the middle of a conversation. Don’t get there and be like, “How was your day?” Get there and be like, “You will not believe what’s happened on the way here.” Jump in, get to know a person, and have a fun time.

I appreciate those perspectives. I agree with you about the mindset of it’s a lot of pressure to be thinking could this be something special? The solo audience has an advantage in some way because they might be already ambivalent about partnering up anyways. In that way, there are more degrees of freedom in terms of approaching a coffee or a drink. I always think of it as like, “This is going to be fun. I’m going to meet a new person.” If it goes horribly awry, I have a great story. There’s almost no downside that comes from meeting someone that at least at the outset you’re excited to meet. That was my point about the flirting, Jill. It’s nice to say to someone something about you’re looking forward to meeting them and meaningful with regard to them because I’m not saying something could be a strategy too. That’s to your point about being authentic. If it’s in your nature to do that, then it seems okay.

Daliya, I stalked your website before.

What website was it? What’s the name of that website, Daliya?

It’s DaliyaKarnofsky.com or something like that. I’m not sure but I looked at it and I have to say that something I loved about it was that how often was how often you mentioned fun that, “It’s supposed to be fun.” We forget that sometimes when we think about the possible outcomes, consequences, and all that. It was funny, I was like, “What am I going to say because Daliya is going to be talking about fun. I have to come up with something else.” I do think you’re right in that regard. When you go into it with a lot of expectations, a lot of ideas about what is going to happen, and what this is going to mean, you forget to be there and get to know the person. Here’s the thing, it’s not going to go how you think it’s going to go. You don’t know how it’s going to turn out so you might as well go and see.

Be open to it. I have this example. I think it’s a good parallel example. A good friend of mine is a competitive dancer. She said she does her best dancing in a competition when she goes in, looks at the field, and think, “I don’t think I’m expected to place in this competition. I don’t think I’m expected to win here. Whatever. I’m going to go up there and dance.” She said those are the times when she has her best dances. She might not win the competition but that’s when she feels and does her best. That says a lot about when you’re not thinking about the outcome or you have this way that it’s supposed to go. You can have the best time, feel your best, do your best, and have the most fun along the way. No matter what happens, you’ve won.

This will be a little quiz for my two guests. Right before we went on the air, what did I say?

You said have fun.

I said be authentic and have fun. Jill is saying be authentic and Daliya is saying have fun. The same rules apply for a date.

If there’s something that’s keeping you from having fun on the date, you’re hungry, cold, you want to sit somewhere else, you need a drink, say it. Put it out there for your date to help you have a better time.

That’s such great advice because you might name something that they were thinking too.

I know a woman who went on a date, she now lives with this man but in the first half of the date, he was talking and not asking her any questions. She had to go to the bathroom, she goes, “I’m going to go to the bathroom and when I come back, if you don’t start asking me questions about myself, I’m leaving.” He was like, “I didn’t realize I was doing that.” People get nervous and now bliss living together or whatever. It’s about being honest, being authentic and if there’s something that can happen to make you happier, why would you not say that?

I’m going to switch that around. That’s a good segue for the actual meetings. We’re already in there talking about it because it’s such a big part of this process. How to deal with the opposite of that situation, Daliya, where you’re getting interviewed? The person comes in, they don’t have the fun authenticity perspective here. They’ve got their clipboard out, their checklist, and they’re asking you the hard-hitting questions, red flags.

I hate it when they shine a spotlight in my case.

That happens because people are tired of dating. They have goals. They think they know what they like, what they want, and so on. What do you think?

First of all, that person needs to be sent to me for some coaching because I would never allow that.

I’m glad you said that because what I have been talking about this is someone who feels he gets interviewed a lot, but there are readers who are interviewers. It’s important for them to hear how off-putting that is.

It’s extremely off-putting. It’s fine to ask a question but then once the person answers, you have to have shared your experience as well. If you’re firing off questions, they don’t feel like you’re listening to them. They feel like you’re trying to get through a checklist. You ask a question for the purpose of it and hopefully turning into an interesting dialogue where two people get to know each other better. Not to get like, “He answered that question. That’s a seven.” If someone is doing that to you, that’s a tough one. You want to try and slow their rhythm down a little bit. You want to do something to get through to them what they’re doing.

It would look like one asking them questions back is a big one. If they’re asking you, you can be like, “Okay but I’d love to hear something about you. What are you passionate about?” Some other back pocket questions you have. The worst-case scenario is you could be like, “I’m having such a great time with you. You’re asking me a lot of questions. I feel like I want to know more about you.” It’s being honest with them, they might not realize they’re doing nerves. I always give everyone the benefit of the doubt because most people are not professional daters. You can be like, “Tell me a story about your childhood.” You can stop it in its tracks.

I was thinking that because here’s my take on this. It comes back down to authenticity. Some of the best dates I’ve ever been on have been the ones where I walked away from the date and my friends would ask me, “Does he have any brothers and sisters? Where is he from? What does he do?” I’m like, “I don’t know. We didn’t cover any of that. We were talking about stuff like bugs on the sidewalk. I don’t mean to harp on that point, but you get the idea.” It represents to me banter. For me, personally, is my favorite thing. If it feels like an interview where I got a bunch of statistics on the guy but I don’t know how he feels or if he has a sense of humor then maybe it’s worth a second date if there weren’t any real red flags, as we said. If there was banter that flowed then I know there could be something there but that’s me. For someone who’s a little more serious about finding a father for her children, she needs more of an interview and wants more of an interview.

That will never ever work.

First of all, I will point this out, this is for the guys who are reading traditional roles. Guys, you cannot do all the talking and not contribute and ask. There’s a lot of men out there who are like, “I love it. Keep these questions coming.”

They love it when the women ask a little question.

They do in that way so that contributes a little bit to that, it’s not. It’s not right because the woman walks away and she goes, “He doesn’t care about me. He’s not interested in me.” This idea of banter, fun, flirt, and the middle of the conversation is a nice way to put this. You were shaking your head about the father of your children thing, Daliya.

A person you just met, if you say, “Are you looking for a relationship in your future?” they’re going to say, “Yes.” Is that going to give you any information? No, it is not. Anyone you interview with those types of questions early on, they can say whatever you want to hear and then you’re going to be shocked when it turns out not to be true. I have a client who falls prey to this all the time. She’s always like, “He said he was looking for love and a wife. He wants to have kids right away.” After three dates, he’s not interested and he says, “You’re at a different place in your life than I am. I’m not looking for a kid.” She’s like, “He said on the first date.” I’m like, “Because they know what you want to hear and they’re trying to get the answers right.” You’ll never going to get the information you need from that interview. That is going to come out in little hints throughout the relationship. You’re eventually going to have a real conversation if you need to but your first day, find out what they care and passionate about and if you like hanging out with them.

I don’t like it when people lie or misrepresent. In some ways, it’s not an outright lie. This is a problem with the abstinence with these conversations more generally is you say to someone, “What do you want?” The honest answer is, “It depends.” I could want the full boat, some friends with benefits, a couple of dates, or heavy make-out sessions. It could be, “This is it, the next 45 minutes is all I want.” The honest answer is, it depends on how much we click, what’s going on, how busy I am with work whether there’s a global pandemic, and so on. The apps are like, “You got to decide. Do you want this, this, or this?” It should be, you could check all of these things like, “I might want something casual or serious.”

You should always assume. It depends if you’re a match and that will determine what they want with you.

I want casual and then three months from now, it might become more than casual. I like it when people are honest. It’d be nice to have more of that where someone says, “I’d like something casual, but almost all of my relationships started off casual. It takes 2 or 3 months for me to decide that I want to be exclusive with someone I want to be a traditional girlfriend or boyfriend.” Whatever that might be.

The most important thing to me is do I enjoy this person’s company? Do I like what they say, how they think, how they behave, and everything? I completely agree. Everything depends on that. I don’t know if they’re shooting themselves in the foot and this is something they’ll evolve to over lots of disappointment in dating from doing the interview and not getting what they want. If that’s where that person is, I don’t know if there’s any changing it except through their own series of unsuccessful experiences.

They need to go to a sperm bank where you can look up all of those answers. They’ll write them down for you. Any information you could get from a sperm bank should not be questioned on the first date.

I’ve talked about this on the show before and it’s difficult for people to do, that’s to ask for what they want in the sense of responding to that question. If we’re going to lean into the authenticity, what you have to do is risk the person who has the checklist, who might be a good partner going away versus to misrepresent yourself do harm to that person.

I have some thoughts on that because it’s important to not misrepresent and to be honest. I also think it’s important not to have an attack of honesty too early on. It was messaging or it was a date, I’m not sure but where a guy said, “Here’s my situation.” I don’t think we’d even met yet. This was in a message. There was the litany of the laundry list of problems. At that point, I was turned off because, “Here’s the thing. I don’t know anything good about you yet to balance out all these potential issues.” Before you give the person all the reasons that it might not work out or not to like you, give them a few reasons to like you. I don’t think it’s being dishonest. You don’t have to have an attack of honesty before you’ve even met the person. There are also some true things about you that are positive, green lights, and all that. Build a little rapport, connection, and foundation before you take a sledgehammer to it potentially.

Hopefully, we never take a sledgehammer to it.

Before you give the person all the reasons to say no, give them a few reasons to say yes. I don’t think that’s being dishonest. That’s building something before you say, “Here’s where we might have some challenges.”

Let me ask a few quick ones here. Daliya, you eloquently said if you could find out about it at a sperm bank donor profile, is there anything else to not talk about on a date?

My number one that people do all the time because they’re nervous and they default to it is talking about dating on your date, “How’re the apps for you? Do you do this a lot? What was your worst first date? What’s your most embarrassing date? How long have you been dating? Tell me about your past relationships.” Why would you ever talk about that on a first date? That is the ultimate friend zone, it is not sexy and interesting. Past relationships don’t even matter unless it’s something that’s going to significantly affect the way you are in this relationship and then that can come out later. On a first date to talk about dating makes absolutely no sense to me. That’s what I say.

I totally agree because when they’re like, “What have your nightmare dates been?” I’m like, “I don’t know, maybe this one.”

“Do you have nothing else to ask me about?” “I understand we both have that in common. We are both dating and I have nothing else to talk about.” Ask them about the bug they saw on the sidewalk.

Is there anything else that comes to mind?

I don’t talk about politics or religion. If those things are important in your life, authenticity, talk about them. I don’t talk about it except for what I said.

What about wrapping the date up? The audience asked, “I know this is a stupid question but I literally turned down a lunch date with a guy who was adorable because I was stressed out overthinking about how to handle the moment the check came to the table. Not that I don’t want to pay, it’s awkward.”

I have some thoughts, but you’re both not going to like them.

I know what Daliya’s thoughts are. Jill, do you know what her thoughts are?

No, I have no ESP or mind-reading ability.

The guy pays. The guy picks up the check.

The woman shouldn’t even do the reach because it’s fake and they know it’s fake. My exception to that is if you know you don’t like the guy or you’re not into him in that way, then it’s a clear signal when you offer to split that it’s platonic for you, for most women. There are some that insist on being “equals” and paying because that’s who they are. That’s fine if that’s your thing. Women put in so much financially in many other ways, there’s also still a huge pay app and I call it the patriarchy tax. I put my safety insecurity at risk unless you’re a woman who grinds your gears, you should let the man pay. On the 2nd or 3rd date, you can be like, “Would you like to split it?” Let’s say you go to another bar, you can be like, “I’ll get this round.” If you get coffee after lunch, you can be like, “I’ll get the coffee.”

Daliya, you think I’m going to disagree with you? I’m not going to disagree but I’m going to disagree with the reasoning. Without getting into the economics of the pay gap and all those things or any of this stuff, I go by the thing, “I ask, I pay.” The reason I do that is that it’s the norm. Why fight against this current? Even though I consider myself a feminist, I have egalitarian ideals, and the guy picking up the check doesn’t jive with those things, it’s common that it’s the best default to do. I pick it up happily and I resist any attempts to have it split. I won’t if we go somewhere else and this person says, “Let me buy a drink,” or something like that. I might resist a little bit, but I’m not going to put someone out who’s being authentic. I come to the same conclusion as you, but for wildly different reasons.

I’m into your reasons too. I’m into all reasons for this.

Jill, do you need to go against the grain?

No. This is traditional but I love feeling female. I love it when a man feels like a man. There’s going to be a lot of people who don’t like that but that’s how I feel. I love that feeling of being taken out by the man, particularly on the first date. That’s a nice masculine-feminine thing. I enjoy it and I’m a woman who takes care of myself. I’ve have been independent and supporting myself for years and years, and yet I still love it when a guy takes me out on a date. That being said, if that’s not you, if you have a different slant on it, for that woman who wrote you that email, she can always ask like nothing dispels awkwardness saying, “This is awkward.”

If she’s feeling awkward, a great thing for her to do at that moment is to say like, “Here’s the awkward moment where the check comes and I never know what to do.” Diffuse the bomb by saying something about it. You’re being yourself and you learn something about the guy by how he reacts. He might say, “I get it. I hear you but I would love to take you out. Is it okay if I pay for it and you want to pay for the next one or we can talk about it the next time it comes up?” That feels sad to have it be a reason not to go on a date at all.

It’s illustrative because my guess is the three of us are good at this. A lot of people aren’t good at it. It’s a fraught process. It’s why I’m doing this show.

I was going to say that’s why we’re here, so if someone who feels more uncomfortable with it can read this blog and be like, “I can say something when that moment comes.”

I love what you said about it because then you can apply to non-gender stereotypes that whoever does the asking, whoever has the request is saying, “I would like to take you out.” That’s a beautiful way to look at it.

I ask, I pay.

If I’ve asked a guy out and the bill comes, I look at him and I say, “This was my stupid idea. Can I pay for it?”

I will give you one exception to this. It started off a little bit casually but we ended up dating for over a year. I remember this distinctly. We went out to a Thai restaurant in her neighborhood and it was our 1st or 2nd. It could have been our third but not even that early. The check came, I went to pick it up, and she offered, I said, “No.” She goes, “Really? If you don’t split this with me, it will be a problem.” That was for our entire relationship. We would split a check or we would alternate. Even at one point, she treated me to a weekend away in a boutique hotel. I have to tell you, it was refreshing. It was neat to have that different experience.

She’s being her and you responded well to it. If the guy who doesn’t respond well to it, that’s not her guy.

The guy who couldn’t be comfortable allowing himself to be treated for a weekend.

It’s clear that was something she had to do. She felt strongly about that. She said something to you. What I love about that too is that she risked it. She risked saying something to be true to who she is because you might not have reacted well to it then she risks losing you but she was true to who she was and it went well because you were open to it. That’s cool.

That’s a nice exception. That’s nice because it shows you that there’s no one rule for everyone. The last thing, you’re wrapping up the date, you’re on the sidewalk, Jill. What happens?

I was hoping you would ask Daliya because I am bad at goodbyes. Talk about awkward. I can extend a goodbye, hem, haw, and stammer like nobody’s business. It is bad. I don’t know how to quickly wrap it up.

Do you want to pun to Daliya?

Can I pun to Daliya, please?

She’s a pro.

I am a huge fan of the kiss. You’ve got a lot of information from that. It can make you attractive to someone that you didn’t know you were, however, if you’re not feeling it, you’re not a first date person, that’s totally fine with me too. A lot of people will say, “What if I want the kiss and he doesn’t kiss me.” I say you can say, “You can kiss me.” If you would like to kiss and you’re not sure if you should, you can always say, “Can I kiss you?” which is a beautiful thing to do. It’s nice to make sure whoever needs it that they’re safe, they’re getting in their Uber, you say, “Text me when you get home.”

I work also with a matchmaking company. I work with traditional gender roles a lot. Usually, the rule for the girl, if she would like to go out again and say, “Thank you. I had such a great time. I’d love to do it again. Let me know.” That’s dropping the hanky of like, “I’m telling you yes but I’m putting it in your court and you have to do something if you want.” For whoever is initiating, I love to say make a plan for the next date before even leaving.

If you’re clearly both into each other and let’s say she said something like, “I love getting tacos at this place.” You said, “We should do that on Wednesday,” or, “Do you want to get tacos at that place you said on Wednesday?” Nowadays, everyone is so wishy-washy like, “We should do this again. We should hang out sometime. You were cool. We should chill again sometime.” If you can be the decisive proactive person who’s like, “I like you so much that I’m willing to risk it.” That says a lot.

We’re not fighting but I want to offer some counter.

I know sometimes it puts people in an awkward position. That’s the part I would say, if you’re not comfortable doing that, if you’re not sure how it went or whatever, then say, “Good night, thank you. I had such a great time. Text me when you got home. Let me know you’re safe.”

This is great especially because Jill is like, “I don’t know what to do.” She could watch battle this out. About the kissing thing, as a guy, I like the idea of asking. If you’re unsure, you can ask. There is another little bit of a cheat code, which is you look into the person’s eyes and then you move forward. What will often happen if she wants to kiss you, she will kiss you. If she doesn’t, she’ll turn her cheek and you give her a peck on the cheek. That kind of a thing. To me, I don’t feel pressured to have a kiss at the end of a night if I know I like someone.

You’re so tall, she has a long time to get away if you want to do it.

She could be in the car or in bed by the time I get down there. To your point about solidifying attraction, I had this exactly like that, the car was coming and reaching. The kiss was out of this world and ended up dating the woman. She is an extraordinary kisser which is a matching process. Everybody thinks they’re a great kisser. Everybody is a good kisser if you match them up with the right person, but you don’t know until you try. I prefer a cooling-off period. I’d like to sleep on it. I would say as the person who asked, you should always thank them. Even if there’s no intention of going out again, it’s important to acknowledge that person. They took a risk, they spent their time, they got dressed up, they did all those things and to send a text message, “Thanks for meeting. I enjoy talking to you.” Whatever that could be. If you don’t want to go out again, full stop.

I say more for when people get asked out again and they’re not interested that you can say, “I had such a great time with you. I didn’t feel a romantic connection but I wish you the best of luck.” It’s better than ghosting or giving some other excuse.

I feel like we’ve talked about this offline or in the previous one, but as the person who asked on the first date in the expected person to ask again, it’s awkward and even means to tell someone you’re not going to ask them out again. To me, you say you had a nice time and then you don’t ask or you say you had a nice time and then you ask. If someone presses you, you say, “It’s not the right chemistry.”

The cooling-off period is fine. If you do decide to do what you want to be specific, you want to be proactive, you want to show them your enthusiasm a little bit.

[bctt tweet=”A date is an opportunity for a great story, a business connection, a friendship, or more.” via=”no”]

I agree with that.

It’s important to be a good citizen of the dating world. As a world where we influence each other and we create the feeling, we create the atmosphere, we’re part of the group that makes the feeling. It’s easy to get frustrated because there are a lot of people who ghost and who aren’t great citizens of the dating world who lie. Particularly where this is concerned, it’s a place where people can get hurt or confused. It’s nice to give someone clarity especially if you can tell that they’re interested in you and you’re not interested. It’s nice to say, “Thank you. It was nice to meet you, but I don’t see us as a match. I don’t think we should go out again.” That’s all you have to say. It gives that person that bit of respect and kindness because you influence how that person feels. If you don’t do that, then they get more frustrated, and then they’re less apt to behave a good citizen of the dating world. They’ll ghost people too so we can bring up the level as opposed to keeping it low.

Jill, that is such a good parting thought. I can’t say it better myself. Can I let that stand for you?

Yes. I love that.

Daliya, do you have a parting thought? We’ve covered the planning, prep, meeting and we covered the follow-up. We’ve got through all of these steps that I had promised at the beginning of this. Anything you want to add to this wonderful idea that Jill said?

In general, raising the dating karma is the way to go, making other people feel better and assuming positive intent. Remembering that this is a process and it takes a long time. If you walked into a bar with 100 people in it, it’s not even necessarily true that one of them would be the person you’re going to date. People who are trying to shortcut the process or make it results-oriented, I talk a lot about this in my coaching is it has to be a process and you have to find a way for you to enjoy the process. Figure out how you can enjoy it. What can make it fun for you? If you need to take a break, take a break, come back in with a positive attitude and expecting it to be a journey. Every day you have is an opportunity for a great story, a business connection, a friendship or your partner, if that’s what you’re looking for.

That’s well-said given the readership here, there are some special considerations, which is not everybody might be on that track of two, have kids, a white picket fence and so on. I think that everything that we said is applicable to the solo dater because none of what you’re suggesting is specific to that person who’s looking for the traditional approach. All the normal caveats with regard to recognizing the limited traditional gender role stereotypes that we’ve dealt with here. I should follow this up at some point with a more unconventional how to date episode. That would be useful. I want to say thank you to both of you for your generous time, thoughts and ideas. Until next time, I’ll say cheers and onwards.

Thanks for having me back on the show.


Important Links


About Daliya Karnofsky

Solo 41 | How To Date

Daliya Karnofsky is a comedian, performer and dating coach. She works privately with clients on everything from online dating profiles to breaking up and moving on. She hosts the podcast Not Your Therapist, which is one on one dating coaching guests both anonymous and not. She is the co-creator and co-host of the live show All My Single Friends, which is half comedy show half live dating app in Los Angeles. She also returns from being featured on Episode 16, Making Single Friends and More – where she critiqued Jill and Peter’s dating profiles.


About Jill Cohen

Solo 41 | How To DateJill Cohen grew up in Miami, attended Emory University, received a masters in English from the University of Colorado and resided in Boulder for many years. As a travelling ER nurse, she worked in Colorado, Wyoming, California, Florida, and Australia. She joins the podcast from Truckee California, where she recently started working as nurse for a virtual medical team. You may recognize her as a guest on Episode 10, What Makes a Life Remarkable.


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