This week, Jake goes out with model and dating coach Tiff Baira. The two discuss people who bring laptops to bars, building self-confidence, and the best places to meet men in NYC. Tune in for more.

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Jake Cornell: Thank you so much for doing this.

Tiff Baira: Thank you for having me. I’m so excited to be here.

J: Yes. Okay, we were just talking before we started recording. You’ve lived in New York, did you say eight years? Seven years.

T: Seven years, yes.

J: Okay, seven. Gorge. The thing I was most excited to talk to you about was — I made a long list, but we haven’t heard — you do dating advice and one could call you a dating expert. The show’s about going out. We talk about going out all the time. We haven’t really done the dating deep dive and I do think that’s an exciting place to enter. Is dating the main way you enjoy going out?

T: Absolutely. I feel like I love trying the restaurants more than the men. That’s like my-

J: Absolutely.

T: Okay, I think my approach is a way of merging the fun of going out with dating. I think a lot of people put pressure on themselves to find the one. “I need to find my husband tonight,” and I’m like, “Girl, you’re not a tire. Stop putting all your pressure to build your life. Go out to drinks, go out to dinner. Make it more of a experience rather than an expectation.” That’s so you can actually learn how to enjoy dating again.

J: Thank you so much. I totally agree with that, I think it’s the same because it’s funny that you say this about the dating site because I often talk about restaurants. Where I think people approach restaurants and you just like, “I need to get this right and nail the experience.” Especially when you’re going to a restaurant that ‘s like a place to go. If you go to like, I don’t know, like f*cking Balthazar, it’s like being like, “I have to do it in a certain way,” and I’m like, “Or you can just do your version of it.”

T: I totally agree. I feel like the point of dating someone is you could either be at Balthazar, or you could be with a bottle of wine in the park. It’s about getting to know someone. Of course, have your expectations of what you want your date to look like. For me, I don’t want to go over to a guy’s house at 4 a.m. and eat Cheetos on his couch and watch “Game of Thrones.” It’s not a date to me. If that is a date to someone respect that.

J: Respect.

T: You have to make your own boundaries and you have to also make your own ideas of what you feel comfortable doing.

J: Also not going in, I think what’s interesting about what you just said, and this is how I used to feel — sorry, I just realized I was talking about dating in the past tense, but I’m single now so I can talk about it in the present.

T: Yes. Already. Cheers.

J: Jesus Christ. That’s often a thing I think about dating and especially when I was dating when I was younger, I think a lot of people I know approach dating, like you said, with the end goal, “I’m finding my husband. I’m finding my boyfriend. I’m finding my girlfriend. I’m finding my wife.” Whatever. Whereas, what it actually — all it is, is like, “I’m meeting up with this person to get to know them.” If you go on a date being like, “I need to find my boyfriend,” then anything else in that is going to feel like a failure. If you’re like, “I’m going out to get drinks to get to know this person,” unless they literally don’t speak, that goal will be achieved. Then you get to make a separate decision, “Do I want to get to know them? Do I want to see them again?” It loosens the constraints of dating.

T: Absolutely. I also think to add to that, you should go out to get to know yourself too.

J: Whoa.

T: When I go out on a date, I’m going to learn like, “What makes me feel confident? Do I like how this person’s speaking to me? What is my dating style?” If you take it more into an inward reflection rather than “I need to prove to someone my value,” you’ll enjoy it more. Then on top of it, you’re dating like it’s the last date so you can take it for what it is. I think a lot of my clients and a lot of people that I work with, when they have that end goal in mind, they’re already painting a fantasy rather than the reality that’s in front of them. I do this exercise with all my clients. I get them to write everything they want on paper, and then I get a paper shredder after the date. I’m like, “Look, the person that you actually want, you can’t quantify into certain attributes on a piece of paper.” Once you’re on the date, you can actually see what’s in front of you. If you’re falling in love with the future rather than the person in front of you, it’s going to lead you to failure.

J: Your journey to get here as a dating expert, was this something that came naturally to you? Is this knowledge and this skillset something that you feel was innate, like, “I’m just really good at this?” Or is this something that you really worked at and crafted? I’m sure it’s a bit of both.

T: Honestly, I think it’s just a multitude of bad dates and low standards.

J: At some point, you’re like, “I’m going to change this.”

T: I think a little bit about my story, I was really deeply bullied for a long time. I never thought that men would be proud of me. I was always someone that people called after 10 o’clock. I’ve always felt I was someone that didn’t deserve to go on the date or didn’t deserve to be seen with someone. I realized that that was, of course, conditioning from bullying, but also a narrative I was telling myself, so I decided to change it. That’s why to me, dating is so fun because it’s not just going out to get to know someone. It’s like, “I’m going to be who I want to be and present myself to the world and not hide because I deserve to, like, be proud of who I am.” I want to be with someone that’s proud to be with me. All of these advice and tips that I’ve been giving on TikTok, it’s almost a way of giving myself the advice. When I first started on TikTok, I was on the ground floor. I was learning to set boundaries. I was learning to build my confidence, and I was learning to date in a way that made me feel good. As I was doing that, I was sharing it with all of the people on TikTok, which I think is a very nuanced and unique way of being a dating coach because a lot of times dating coaches have been married for 100 years and they’re like, “I’m perfect. This is what you have to do to get here.” I’m like, “Look, babe, I’m not perfect. I’m here doing what you’re going through too, and let’s get through it together and let’s be honest about the realities,” because a lot of dating coaches don’t know what it’s like to date anymore, but I do it five times in a week.

J: I think you’re acknowledging that dating is separate from a relationship, and you’re not a relationship coach, you’re dating coach.

T: Yes. I do think what I give to my clients and what I talk to on TikTok really comes from a place of being confident in yourself, which goes from dating to relationships, to marriage, to divorce. You’re stuck with you through all those phases.

J: 100 percent.

T: I hope that the advice that I give can go with you throughout whatever stage you’re in. I do think my approaches and my tips are heavily focused on dating. I think that if you can learn to love yourself in the most scary moment, which is going on a first date — honestly, people don’t give people enough credit about going on a first date. You’re, literally, going in front of a stranger that doesn’t know you and you’re being perceived, and it’s terrifying. If you can feel strength in that moment, you can continue to build on that. I call it the confidence gym. It’s continuously putting yourself in situations that are outside of your comfort zone when it comes to what are they going to think about me? What should I wear? What should I do? Eliminate that thought process and come from your own standpoint, what do I want? What makes me feel good? I think that can go with you throughout whatever date or relationship or whatever comes your way.

J: Also, those are all things that if you’re going to have a relationship that’s successful, they need to start, like you said, on the ground floor, so coming to it with that. If you don’t start a relationship with that, if you don’t start at the dating level with that level of confidence and self knowledge, it’s going to be harder to find it when you’re further down the line of whatever you end up in.

T: Oh my God, I always tell this to everyone and I had to learn this myself: When you go on first date, don’t be your PR team. I think a lot of us feel like we have to be perfect. We have to present an illusion of what we wish we could be. No, b*tch, you have to be who you are at the beginning. Because guess what? You might get a million people that like you by being something that you’re not, but you’re not going to have the right people, and I always tell you when you don’t need to sell at Madison Square Garden of d*ck, like you just need to find the what. All I’m saying is that it’s better to attract rather than change yourself to fit someone else’s narrative who they want you to be.

J: Are you mostly coaching women who date men?

T: That’s basically the main crew on TikTok. I mostly have a woman-based demographic, but I can’t wait to announce some things that I’ve been working on. I’ve been really working in a — let me rephrase this because I can’t talk about that.

J: No. We can cut.

T: Whatever I was doing.

J: Totally.

T: I’m really excited because as I did start on TikTok, I was mostly speaking to a young girl demographic. However, I’ve really got to expand that, so with my dating coaches, I’ve really worked with everyone across the board.

J: Nice.

T: All sexualities, all genders, and it’s really been great because my approach is something that I think is universal, which is really learning how to lean into your power. Of course everyone has their own unique stories and unique dating approaches and I think that’s why a lot of these dating rules are. Because they try to make a one-size-fits-all for everyone, which does not exist. They’ll be like, “If you do this, you’ll get that person. If you behave like this then you’ll get them. You have to do these 10 steps to get laid.” No. You need to be able to build your own steps to learn what’s best for you.

J: I’m curious in the process of expanding to starting to work with people that aren’t women who date men. What are things that you’ve learned that are different? What are things that you started to realize as you’ve started to coach people who don’t date in the same way you do in terms of gender and sexuality. Are there things you’ve learned? Then I’m sure that also there are things, like you said, that are the universal constants, and those are probably really powerful, but I’m curious if there’s things that you’ve opened your eyes to, as you’ve been like, “Oh, sh*t.” Like, “I was thinking about it this way, but when it’s in this situation, it’s, actually, this way.”

T: Absolutely. I think I’m constantly learning from the people that I work with all the time. Because I think the difference between my approach and some other dating coaches is that I’m not here to tell you what to do. I’m here to help you curate what you already know. I think with working with people that date differently than me, I’m taking in a lot of the information about how they date that might be different from my own experience. From there I really just guide them to do what they’re already doing in a more confident position.

J: Got you.

T: That’s the thing. I’m not someone that’s going to tell people what to do. That’s never been my goal and that’s never been my strategy, because who am I to tell you what’s best for you? I think we all know what’s best for us. It’s just sometimes we need a little guidance or little coaching to help us understand that we do have that power already.

J: Totally. Is most of your social life now dates?

T: It’s crazy because they say those that don’t do, teach, but no. I’m really in the midst of, I don’t know if it’s a 25-year-old life crisis, but-

J: Quarter-life crisis.

T: Quarter-life crisis. When I first started dating heavily — so I told you nobody would take me out until I was 18. I moved to New York. I was a New Orleans negative 100. People scoffed at me. No one would look at me. So then when I came to New York, I was like, “Holy sh*t. People think I’m hot. What? Okay, this guy in a blue suit that’s at the club actually wants to go out.” I’m like, “Okay, sure.” Later did I know that he was really just a Wall Street asshole with a coke problem.

J: Oh. A huge coke problem. I was like, “Why is it that a blue suit is more cocky than a black suit?”

T: No, it’s true. Beware of a blue suit.

J: Blue suits are cocky.

T: Yes, they are.

J: What is that?

T: Addiction. I love how it looks, but beware if you’re dating a guy with a blue suit; he has a secret.

J: Maybe because the powder shows up more on black.

T: No, exactly.

J: Wow.

T: Blue suit, they either have a secret wife at home or problem.

J: I’m dubious of a blue suit. I’m really dubious of a blue suit.

T: Beware. I moved to New York, and then it was the first time that I was starting to be perceived as beautiful, at the same time I got scouted as a model, which was then like a crazy journey for me where I was like, “Oh, my God I spent all my life hating myself, hating my body and now I’m getting praised for it.” It was like an adjustment.

J: What does that feel like when you go from feeling like you’re a negative 100 to being a model? What does that feel like?

T: Ultimately, that’s what made me develop my core beliefs, which is that it literally doesn’t matter what other people perceive you as, as long as you know that you’re b*tch. It’s funny how in one city I’m nothing and in another city I’m a model that relativity is, actually, what is the basis of all my dating advice, who I am as a person, and what I give to everyone.

J: 100 percent.

T: You walk into a room, a 100 people are going to have a 100 different ideas about you, but what’s your idea about yourself? Because you can handle what everyone has to say about you if what you stand for, what you believe, and who you want to be. For me, when I was modeling, of course, now I can say that in hindsight, but I’ll be straight up: It was really hard for me.

J: I’m sure.

T: That’s where I think my heavy dating, heavy need for validation really started. Because it’s crazy, you’re getting paid to be beautiful. If you don’t believe you’re beautiful you still need people to make you feel beautiful. I almost call it like Band-Aids on a bullet wound where I was like, “Okay, I need guys all the time to be so hot, so hot.” I needed my fix. Then I started dating terrible people because I needed people to love me even — I wanted fake love over being alone. I’d rather have a love that hurt than, actually, realize that, like, nobody wanted me. When I would go out to the club, I’d be like, “Oh, my God. No one has flirted with me. I’m so ugly. I’m disgusting,” all that stuff. Which was not the right healthy way to be. That’s what started me dating a lot. I had a lot of fun. I’m sure we all have our toxic moments. Sometimes the most toxic moments can be a lot of fun, but they’re hurting you.

J: Absolutely.

T: I was in college, I was going out every night, I was dating all these guys and I was literally learning what it’s to be myself in an environment where guys like me. Which it was rocky because sometimes — the biggest lesson that I’ve learned from that phase is that just because people are giving you attention doesn’t mean that they like you. Just because people are wanting you to be with them doesn’t mean that they really want you. That was a big lesson I learned from that. A lot of toxic guys, a lot of great moments, a lot of great sex, but that was it. I was also struggling at the time as a musician. Nothing was really going my way. Dating was an outlet for me to just feel good. It was good. I had a lot of fun times, but I know now being like a granny that that wasn’t sustainable. After that, I was working at a private membership club. I was working at a Soho House, and I’m around all these like super-rich people. I was always in the service industry ever since I was like 15. I was working in pizzerias, working in donut shops, doing all this stuff. I think that was another insecurity where coming to New York you never know if it’s this world where no matter how much you do there’s always someone doing more or no matter how wealthy you get there’s always someone with more money or no matter how beautiful you are, there’s someone that you perceive as more beautiful. That was a big insecurity for me. Then I just started to be like, “That’s enough. I can’t keep living my life feeling like I’m not enough.” If you view your life from a point of lack, you’re never going to enjoy it. That’s when I did the switch. Then I started making the TikToks, doing all the advice, all that stuff. I owe TikTok my standards, my life. It helped me become who I am now. I think right now I’m dating, but I’m not dating as many because I’m dating the right people.

J: That makes-

T: That was a long way.

J: It makes total sense. It is interesting to like that. I have mixed feelings about TikTok. Obviously, it changed my life in these really massive ways as well. I do think one of the things that is really powerful about it when you’re someone who’s putting a ton of sh*t on it is you then do get to, especially if you’re someone who’s putting stuff up on it and people are responding to it and you’re creating whatever this is, people are following you in that whole dynamic. You then, like every once in a while can look back at your page and be like, “Who is this person? What is this? What are people seeing this that they’re liking? Is that, actually me?” You can kind of do this analysis and learn things. I think I did in doing it learn things about myself. That I don’t think I was able to see things about myself as an outsider for a second and realize things that I don’t think I knew before. I do think that is a really powerful thing about that app.

T: You can really watch yourself grow. I think at the same time, your followers are growing with you. It’s interesting because I think it’s the antithesis of the perfect life that Instagram tried to make happen. It’s like here’s the mess. Here you’re along for the ride. Of course TikTok still has the glamorizing of things and that’s–

J: I do think it’s like moving that way.

T: Oh God. The clean girl aesthetic, the body stuff. I hate it.

J: It is weird. It is really wild to watch because like I started posting on TikTok and watching TikTok back like late 2019. I wasn’t posting back then. Actually, I was watching, though. I didn’t start posting until 2020, but that was a different app and a different landscape.

T: For sure.

J: People weren’t there to build lifestyle brands, that was not happening on TikTok. TikTok was the mud. Like you were seeing the underbelly. It was a different f*cking-

T: Bring that back. I love it.

J: Yo, I miss it so much. Yo, I miss it so much.

T: It was real, it was raw, and I think that was the moment of TikTok where — I came up at the same time, so we were starting then where it was like, that was where you could really say. You could be totally yourself. The brands weren’t a point of conversation really because brands really just joined TikTok, I would say, in the last year and a half.

J: 100 percent.

T: That was a moment where you’re just saying to say, and I think that’s something that I still try to just consistently do. Of course now, TikTok didn’t allow me to curse so much. I’ve had to like really-

J: I know.

T: They almost took down my account because I was saying sh*t.

J: It does feel weird like, you do have to sense yourself and create this things.

T: I had to.

J: It is this weird place to — I love doing comedy and I love performing on stage, and I love writing, and I love acting. I’m very thankful for the things that social media has done for my career, but especially with TikTok and especially like — more so with TikTok with Instagram as well, editing myself to work within this algorithm, I hate. I hate that I’m curating my voice and stuff at times to work and I’m constantly. I think it’s so impressive with someone like you. Like I haven’t been able to build really something that works within this thing and it feels so authentic, and I think it is so authentic, but it also works within these constraints. Do you know what I mean?

T: No, absolutely, I think like real to me and is what I always tell myself when I start to get in my head because I struggle with self-doubt, I think a lot of us do, but being real is not a trend.

J: Totally.

T: There’s a million people on TikTok, there’s a million people trying to do. There’s people that, actually, have copied my stuff. There’s a bunch of stuff. Again, going back to the dating advice, as long as you’re showing up in your power, that’s all you can do. I feel the same way about TikTok, where it’s like, “I might not be the biggest creator. I might not be someone that’s going to have millions and all that stuff, but I love what I’m doing. I love what I’m saying. I love what I’m trying to be.” Like I love the work I’m trying to put out and change the world with, and it’s like, “Look, I know that there’s ways to use the algorithm and there’s ways to have a lot more followers and do that stuff.” If it’s not authentic to me, I’m not going to do it, and I turn down people all the time.

J: Oh, my gosh, I turn down everything.

T: Of course.

J: Everything.

T: Guess what? TikTok is an ethical responsibility. People don’t think about it, but it really is when I grew up on the Tumblr aesthetic, when I grew up seeing all these bodies and feeling like I was enough, the Instagram models, all that stuff, that was honestly what made me start my TikTok. Of course, I started with like, where to go out and all that stuff, but once it started to grow, I was like, “Sh*t, let’s have a real conversation.” Because I want to make sure that the next generation of phone users of anyone, right, if we can make the beauty standard a little more realistic in my own way that I can, I’m going to f*cking do it. I want to democratize information as much as possible because the gatekeeping in the modeling world and entertainment, I think is f*cked up. I think it’s a way that you-

J: No, and it’s what allows these standards to be perpetuated.

T: Absolutely. It’s like, I want to eliminate the concept of perfection, you know?

J: Oh, yes.

T: It’s a lie and it has serious consequences. I don’t think people, if they realize it and continue to do it, God’s speed, but like-

J: There’s always going to be a version of it is the thing.

T: Yes, of course.

J: It’s just like taking as much power away from it as it can, it’s always going to exist. People will just always be trying to perpetuate that narrative, but taking as much power away from it as possible and creating more of a space for people to enter into to be like, “Oh, this isn’t real,” I think is powerful.

T: I think it’s a double-edged sword because, to your point, there’s always going to be people that really want — we all, of course, if everything could be that perfect, who wouldn’t want that?

J: Totally.

T: I think I’m inspired the most by people that are honest about their experience, and what they’ve been through. I think just, for example, like what we do. With modeling, I see a lot of models, they’ll just be like, “Yes, I just got discovered in the mall and now I’m a supermodel,” or something like that. You hear this with Taylor Swift, and I think I read her story where she’s like, “She was just singing in a coffee shop.” You see all these huge stars and it’s like — I’m a Swiftie, I love her, but it’s like you see all the narratives of, “I just got discovered and now I’m here,” but you don’t see the reality of how they got there and-

J: It’s not true.

T: It’s not true. I don’t care who you are unless you were born into a lot of money and a lot of connections. If you’re building something on your own, it’s never going to be linear and anything. That’s the same thing with your confidence. I think it’s the same thing with going out on dates and feeling good. Like it’s never linear if you’re growing. It’s like why not show, like a 100 steps forward and a 100 steps back, bring people along the whole way.

J: Totally. Speaking of living in New York for the past seven years, how do you like to go out now? What is going out? I know we’ve talked about dating a lot, but are we a restaurant girlie? Are we a bar girlie? Do we like the clubs? What’s the vibe? What’s the interest?

T: I could be any girl you want. Depends on the day. No, but I do agree. Basically, as I’ve gotten a little bit older, my style of going out has changed. Number one, I’m not working in the service industry anymore, so I don’t have hours. I used to work from midnight. I would get out at midnight.

J: Were you a server at Soho House?

T: No. I was a hostess. You were the last one to leave, so I’d get out at 2 a.m.

J: F*ck.

T: Basically, that time was easy because in a way you have your hours, you can make your plans, all that stuff. For me now, my joy and my focus is making the content and going out to learn and see new things. I’m going out a lot to have fun, but I’m also going out to try new places. I would say my biggest way of going out now is to get drinks. I love going to hotel bars, flirting with the bartender. I have a hot bartender at every single hotel bar in New York. It’s how you get into all these places. My biggest tip to anyone that’s going out is know the bartenders, know the bouncers, and that’s your way in. You really need to make relationships that way. I used to be a club rat. I was a club rat for the last probably five years. I know everybody in the nightlife circuit, and I’ve actually started throwing parties now. That’s a new way that I’m going. That’s why I was singles party every month where I try to help people, make new friends, make new lovers, whatever it is because I do think-

J: Is it at a specific venue or do you move it?

T: This one’s at Soho Grand.

J: Fun.

T: It’s really cute. I just had one last Wednesday, but I think it’s really important that we use the digital platform that we have to create in-person connection too. That’s something that’s really inspiring to me. I’m sure like when you have your shows and stuff it’s cool to see the worlds combined. I’m throwing the parties. I’m going to a lot of dinners. I really am trying to learn how to cook, though. I’ve never learned how to cook in my life so I’m trying to find balance.

J: Really?

T: To me, that’s why I’m saying I’m in my quarter-life crisis because I’m trying to find balance because when I was in my early 20s, it was extreme going out partying. I didn’t give a f*ck and then I think I went through a little bit of a granny mode, where I just was living in Miami for a few months and that really shook me to my core. I was a negative 1,000 in New Orleans, but I was a negative 2 billion in Miami.

J: They’re like beauty body standards or psychology.

T: Holy sh*t. I think, in a way, it’s easy to talk about this stuff online when you feel like you’ve gone through it in the past. This was a new level where I was going through it in the present. I was in Miami and I was getting f*cking — people were rude to me about my body being — I’ve never been treated that way.

J: Oh, I’m so sorry.

T: No, it actually is the best thing that ever happened to me. I think taking suffering and turning it into art is like my favorite thing.

J: Sure. It’s very powerful.

T: Taking that suffering that it made me connect back to not only who I used to be, the feelings I used to feel as a young kid getting made fun of, but realizing that like, “Look, there’s bullies off the playground. There’s always going to be bullies no matter what.” It’s like, “Am I going to go back to that young girl that took it?” Or am I going to be like, “F*ck you, you don’t talk to me that way?” When I say it’s the best thing that happened to me

J: You got to revisit it.

T: A little soft launch, but it allowed me to realize like, “Who is Tiff now?. It was a good thing that that happened, but I was really sad. I went through a little depression, so I was home. I was just trying to figure out who am I now. Right. I wasn’t going out as much and now I’m back. I am feeling myself. I pulled myself out of the trenches, rose from the ashes, and now I am like flirting with everyone at the club. Lately I’ve been doing, I only got two nights a week. I love Wednesdays and Thursdays are my favorite nights to go out.

J: Walk me through that. I find this interesting.

T: Number one, weekends are too busy. There are too many–

J: Yes. 100 percent.

T: Everyone’s rubbing up against each other and all that stuff.

J: Lying.

T: Oh, my God. No. It’s literally terrible. If I’m like, let’s say I go to dinner and then things happen then I’ll go out on a weekend, but Wednesday, oh my God. Wednesday’s the best night to f*cking go out. It’s like you have all the people that I guess don’t really work 9 to 5s because they’re out, so a lot of artists, a lot of musicians, all that stuff. Freelancers.

J: Also the people who go out on Wednesdays, when you have a lifestyle that doesn’t — like because the thing about the 9 to 5 vibe is when you go out on like a Friday, Saturday and you’re among the 9 to 5ers, it’s like everyone who’s going out — people who are blown off steam on a Wednesday are tea kettles. Friday, Saturday, Sunday pressure cookers, like explosive.

T: They have a whole crockpot.

J: It’s too much steam. It’s like, “Hey, y’all are up and I don’t like it.” You know what I mean?

T: Oh my God. I was at this other private membership club and I was with all these Google execs. This was like two days ago.

J: Okay, flashy. Jesus Christ. This other private membership club.

T: It just happened, we had dinner.

J: Totally, I was at Taco Bell.

T: I like to have a mix of both.

J: Absolutely.

T: I did order Taco Bell at the end of that night.

J: Hell, yes.

T: That’s crazy, but anyway, so I’m talking to them, they’re flirting with me. They buy his dreams. We’re living life. It was like an art gallery. I’m like, “Why are y’all here? You don’t know about art.” They did it. They were like, “Oh, I just thought there were hot people here.” I’m like, “Yes, you’re right there.” It was an art gallery at this membership club. Anyway, we were talking, getting to know each other and then he’s like, “You look like you’re such a good time. I’m going to the bathroom to do stuff.” I’m like, “Whoa, I don’t do that. Thank you.” He is like, “If you don’t do any substances and stuff, what is your vice? How do you escape life?” I was like, “Babe, I’m living a life.” I don’t want to escape. That was a weekend energy.

J: That’s such a crazy question.

T: Yes. What? You hate your life. Do you want to-

J: How do you escape reality? It’s like, “I don’t know, maybe I don’t have to.”

T: I don’t have to.

J: If you do no judgment, life’s tough, but to like-

T: To ask that in an encounter.

J: Especially in response to someone’s turning down coke, “Baby-”

T: I’m like, “I don’t do that, but thanks.”

J: “Let me just say, if you think coke is the thing that’s equalizing your mental state, Babe–”

T: No, don’t do it.

J: Huge alert. It’s not.

T: It’s not. It makes you feel worse, I’m sure.

J: Oh, the worst of all the drugs. I’m like, “Try drugs, experiment.” Skip coke. Literally, skip coke. It’s so gross.

T: Especially right now. It’s really dangerous.

J: Well, oh, well, that’s like a whole other conversation. Everything is so dangerous right now. It’s so hard to be careful, but like coke is-

T: Masturbating will get you higher than any f*cking drug. I stand by that. Go get a f*cking vibrator. Stay home. Open a bottle of wine.

J: Please don’t do it in a club bathroom.

T: No, I do have a to-go. You always bring it to go, no?

J: A roadie.

T: I always have a roadie. What’s in my purse now.

J: Oh, God, that’s so funny.

T: You never know. There’s no judgment.

J: I’m curious if someone were to go, if someone was, “Where should I go on a first date?” Where are your New York recs?

T: That’s amazing. I just made a video about this, actually. It depends what you want. I know it’s a very controversial question, dinner versus drinks. I like to throw in both. I don’t have a stance. I feel like-

J: Yes, I don’t think we need to pick.

T: Because I also will say like, “If you’re not enjoying the date, get the f*ck up.” I have a 10 minute rule. If I’m not enjoying it in the first 10 minutes, I leave.

J: Wow.

T: Yes, but anyway, places I would go. I recommend dim lighting. L’Artusi in the West Village has this cute little bar now. It was really cute. I love — where did I go on a date recently? The bar at Pastis. I had a really nice time. That was cute. A little Martini moment. Waverly Inn is very romantic. If you want a dinner date, it’s super red booths and all that.

J: We’re going upscale. We’re skewing upscale for the day.

T: You know the guys I like. Are you shocked?

J: Yes, no blue suits?

T: Yes. No blue suits. Here’s my thing. I don’t know if this is toxic, but I always test them. This guy asked me out on a date and I’m like, “Where do you want to go?” Then he told me and I was like, “All right, but if I don’t like it, I’m going to give another suggestion.”

J: Sure.

T: If you want to go in a chill way I really love, Forgetmenot, The Library is this dive bar too.

J: Oh, those are great bars.

T: Yes. Trust me, I can go high and low, whatever we need to do. Whatever the vibe because I date-

J: Yes. Okay. I’m going to ask you to taste.

T: No, I love Grammy musicians with matches on the floor too. It’s like I’ve been to them all. Oh, a place in Williamsburg that I really love is Hotel Delmano. Very romantic. Let’s see. I’m going through everywhere. Rocka Rolla is a good first date spot. It’s a dive bar. I like first dates at a dive bar. Getting to know someone without all of the glam. Now, if you do want to get cocktails I feel like — Oh, the hotel Lobby Bar at the Chelsea, so romantic and the hottest bartender I’ve ever seen. We have stayed-

J: I think we went through an era recently where people didn’t understand that you can go to hotel bars, not as a hotel guest. Some of them are gorgeous and chic. I feel that was a thing that got lost in the sauce for a second.

T: That is the best place to meet men. I have met every single — I went out with Elon Musk’s lawyer a while back.

J: I thought you just were going to say Elon Musk. I was like-

T: Wait, that. No, I would get tuned. I met him at the Beekman Hotel because I went to school at Pace down the street. I actually got my education at the Beekman Hotel. I would skip class and I’d get a mysterious notebook and pretend that I’m a moody student. I’m an English major. I was a philosophy major, that’s an-

J: That’s the moodiest of all. Are you f*cking kidding.

T: I know. No, literally. I’d just be, “I’m just writing my thesis.” When you’re flirting with someone at a hotel bar, your voice goes down. You have to be like, “Yes.”

J: Well, people are sleeping upstairs. You have to whisper.

T: Walk me through this step by step. You’re showing up to the hotel and you’re just like, “I’m going to post up at the bar and someone’s going to approach me.”

J: That is it. That is what always happens. I am a huge solo diner. I’m a huge solo drinker. That is the best way to make friends. It’s the best way to meet men in the city for me.

T: Okay. What are you doing to conjure that energy in when you’re sitting solo at the bar?

J: Okay, so, number one, I feel this is universal in the sense that you need to learn how to sit with yourself. If you can’t sit with yourself, no one’s going to want to sit with you. Just that if you don’t find yourself interesting, no one is going to find you interesting. Those are exercises that I’ve done. I’m an only child, so I always used to do that because my parents were working. As soon as I had a car, I was roaming around because I’m like, “Why the f*ck am I going to wait to live my life just for someone to do it with me?” I just always prioritized experiences even if I was alone.

J: Totally.

T: If I’m going out to eat alone or going out to get a drink, I think accessories are very important. Make sure that you have a book or a little journal or something like that.

J: The tools.

T: A little tool. Just something. Don’t look at your phone. The phone is the worst way to like — it’s a turn- off.

J: Because then you actually look busy. You look like you’re working. You look like you’re on a conference call, you’re on a Zoom in the middle of the hotel bar, babe. I think it’s good to have a more relaxing accessory. I always-

T: Screens kill the–

J: Screens kill the vibe.

T: Kill the vibe. Let me just say this. Right the f*ck now, I hate a motherf*cker on a laptop in a bar or restaurant after 4 p.m.

J: Realize that, “What the f*ck are you doing?”

T: F*ck off. If the sun is down, put your f*cking laptop away. I mean this with every cell in my body. That makes me so mad. Every bar I’ve ever worked at, if someone pulls out a laptop, I’m like, “Put that sh*t away.”

J: Absolutely.

T: “Not here. Absolutely not.” I mean this, I’m dead serious, “F*ck off, go work somewhere else. That is not what a restaurant or a bar is for.”

J: Go to f*cking WeWork? Like, “What the fu*ck are you doing?”

T: People are there to have a vibe and experience an outlook from your f*cking laptop, is ruining it for everyone. That sh*t makes me so f*cking mad. I’m sorry, I just derailed your point, but I don’t think I’ve expressly said that on the podcast yet.

J: I’m so happy you made that clear.

T: Screens, phones, obviously, you can’t expect a club to be phone-free. Especially in a nice cocktail bar, the less we’re seeing phones, the more the vibe is going to be sexy. A laptop has got to f*cking go.

J: No, it’s absolutely unacceptable. I’m 100 percent on your page.

T: That just really hit a vein for me.

J: No, I know. I feel like when you go out alone, back to, “Bring your laptop.”

T: You’re like, “I do love an iPad.” Oh, my God. No, I think it exudes a confidence to be able to go out alone.

J: 100 percent.

T: If someone’s judging you for going out alone, that means that they’re too insecure to do it. I think going to music shows, I don’t know, it depends where you feel comfortable, right? Start with one place, go there often. Create a relationship with the bartender.

J: So important.

T: Because the bartender is actually your connection to meeting other single people. If you’re friends with Eddie the bartender — this happened to me, I was at Bemelmans. I love going there alone just to feel like, I don’t know, like my life makes sense.

J: That’s luxury.

T: No, I love it. Honestly, I feel I live in squalor most of the time, so when I just get up. I feel there’s two extremes to me. I don’t get dressed, I don’t do anything. I stay at home and-

J: Gremlin.

T: Yes. I’m gremlin. Gremlin vibes only. Then it’s like, “Okay, I’ll lean into this two nights a week, three nights a week.” Every time I’ve met someone because I know the bartender and they’ll connect you to other people. That’s the first thing. Then after that, flirting in real life is something that a lot of people struggle with.

J: That’s the best thing in the world.

T: It’s so simple. There’s three steps. It’s so, so easy no matter where you are, eyes, literally deep into someone’s soul. Give it three seconds. If they make a cute little smile or like, look you back in the eyes, it’s on. If they don’t read the room, move on. We all get humbled. It’s okay. Rejection is a way to redirection. You’re all right. Then you do it to someone or next to it. I say that finding love is literally just luck in location. When you walk into a room, you do a Scantron of the room, you got to see where everyone’s at. If you see someone that you think is cute, definitely, find a way to position yourself close to them. If there’s an empty bar stool, go there. It’s going to be hard for you to talk to someone if you’re literally,

J: You’re playing in the paint, you’re playing hardball.

T: Oh yes, I’m ready to go.

J: I love it.

T: You got to have a strategy.

J: Absolutely.

T: I date consultants, but I am a strategist.

J: Here’s a question I have. Obviously I’m dating men, so it’s a little bit different. I’m trying to put myself in the shoes of being someone in a bar, in a hotel bar and seeing someone at the bar that I think is attractive, reading a book, writing in a journal, whatever. What is the way, in your opinion, to make the approach that isn’t invasive, corny, but sexy?

T: Of course. I think definitely reading the room and knowing the vibe in a way that like — that was-

J: I came across Bemelmans in a clown outfit. Like, “No.” Yes. “What are you reading there? You come around here often, baby?” To me there is a few ways to do it. I think the sexiest thing is being inquisitive. If I saw someone reading something, and I honestly, a lot of times I get hit on before I hit on someone else. I do hit on people too.

T: That’s how I-

J: Come on.

T: The reason I say like, the venue is really important. I think if someone is doing that and you know the book, that’s already in, in. Find a commonality. Everyone likes a compliment and everyone wants to talk about themselves. If you can lean into those two things, you’re fine. I don’t think it’s too intrusive to be like, “Hey, so wait, I read the first edition of that ‘Harry Potter.’ What’s the second one about?” Or something.

J: If someone asked that, I’d be like, “Read the second ‘Harry Potter.’”

T: I have never even watched “Harry Potter.” I don’t even know what the f*ck — did I say edition? What is?

J: They changed it in the second printing.

T: Whatever.

J: Oh God.

T: All right. Let’s regroup. I would say — okay.

J: If someone said that sentence, “I read the first edition of that ‘Harry Potter.’ What’s the second one?” I’d be like, “Human trafficker. You can’t even speak the English language. You’re an alien who’s here to, in disguise, to take me off this planet?

T: Let’s take “Harry Potter” out of the f*cking mix. No, basically if someone’s reading something, you’re like, “Oh, do you read whatever a lot?” Ask them a question about what they’re doing, or if you like their shirt, I’d be like, “What is Babes?” What do you say? I can’t even read the shirt.

J: It says Bimini Babes. It’s a drag crease queen.

T: I would just be like, “Oh, I love Bimini Babes,” even if I don’t know what Bimini Babes is. Or like, “Tell me about Bimini Babes.” It’s asking questions about them in a way that’s normal. I wouldn’t be like, “Hey, babe, what’s your Social Security?” I don’t hit on people too early. I think it’s really corny and cheesy to be like, “Wow, you’re so beautiful. You come around here a lot.” In a way, don’t make it about looks off the bat. I think you want to make sure that the person you’re talking to doesn’t feel like you’re going into their space.

J: There’s something about the — because I’m saying mysteries enticing is so viciously corny, but saying-

T: No. It’s true.

J: If someone starts up a conversation with something like, “Yes. Oh, what book are you reading?” If there’s a second, there’s a slight chance that they might, actually, just be asking the question and not flirting with you–

T: Yes. It’s so true.

J: Then you’re like, “Are they flirting?” Whereas if they’re like, “Nice ass,” you’re like, “Well, they’re flirting.” Do you know what I mean? That uncertainty for a second, at some point in relationships you do need clear and healthy communication but at the beginning-

T: Not the beginning.

J: No.

T: Keep it toxic

J: No, actually, wait, I literally was talking about this with my friend the other night in a bar and it’s, “Actually, in the beginning, keep it a little toxic.”

T: No, I agree. I think it’s really sexy, not necessarily know what people want. In the way that you don’t know, to your point, “Are they flirting with me? Do they, actually, just like this book? Do they want to actually just have friends?” I think it’s good when you’re talking to people to not, going back to our original point about, “Worry less about the end goal and worry more about just getting to know the person across from you.”

J: A 100 percent.

T: If you came up to me at a bar and were asking me about my book, I would tell you, “Because I just want to talk to you.” I don’t have a goal in mind. Now, if the vibes were good and it was immaculate and we were attracted to each other, then that would lead into the next step, but stop making everything off the bat about either getting a relationship or getting laid. Just talk to people. That’s honestly, it’ll make you more relaxed, which makes you more fun to talk to, and it’ll get you closer to your goal. I don’t know if you do yoga? When you’re doing yoga, you are repeating the same sh*t over and over again and you just naturally get more relaxed. You don’t just do it with the goal of getting relaxed. When you’re trying to fall asleep, if you want to go to sleep and you’re forcing yourself to go to sleep, you never fall asleep. I think it’s the same thing where it’s like, be open to conversation, be open to getting to know people and just f*cking talk sh*t. That to me, talking sh*t will get you in a relationship eventually.

J: Yes. With your dating and with your going out, does being in a relationship feel like a goal if you love dating this much? Do you know what I mean?

T: Yes. I’ve been in relationships. Wouldn’t recommend. No. Genuinely, I’d fallen in love once and it was a really beautiful relationship and I actually think that he was sent to me in my life although not forever to remind me of what I deserve. Now, when I’m going into my next relationship, I’m open to it. Everything I’m talking about now to what I think people should do is also my approach. I’m not forcing a relationship and I’m really open to different types of relationships. I feel like at this moment, I’m not here to say what I want right now. I’m here to explore and I just want to go out and meet cool people. That’s my goal right now. I went so long without sex, which was a really cool moment for me, actually, to where now I’m not thirsty.

J: Yes.

T: Honestly, I always used to feel like I needed my fix all the time.

J: Totally.

T: After my relationship, I just stopped having sex for six months, and it’s honestly been awakening.

J: Yes.

T: Now, I’m dating at a desire and not desperation, and I’m dating because I want to, not because I need anything.

J: Right.

T: I pay my own rent, I have my toys, I have great-

J: Your roadies.

T: My roadies. I really am at a point where I have everything I want in my life, and I want someone that’s going to add to it. That’s something that I’ve never had before. This is the first time in my life where I’m dating as an equal and as believing that I deserve to be treated as an equal. That’s something that I think is so inspiring to myself and I’m not getting as many guys, but it’s fine. I’m going out and meeting people and having fun.

J: It’s because there are different kinds of dating and there are people that approach dating being like, “Who is the person that’s going to complete me or complete my life?” Then there are the people and I think that’s common because that’s what we’re trained to think. That’s what we’re taught, but then it’s you, actually, who have these relations — you can, actually, go into dating being like, “I’m good. We got it all figured out. If there’s someone else that wants to get involved, I’m open to that, but I don’t need anyone.”

T: There’s room on the list. We’re not at capacity yet. I do think another thing I want to touch base on. Another thing I want to talk about too, is going to your question about what dating and all that stuff with going out? There are some people that just want to get laid. There was a time in my life where all I wanted to do was that, and that is so fun. I want to talk about meeting people if you do want to just get laid.

J: Please, let’s talk about it.

T: I think that’s actually a different dance that people don’t talk about either.

J: Absolutely.

T: The way we talked about the “Harry Potter” edition when approaching someone if you think they’re hot at a club is going to be very different than approaching someone at a hotel bar. A lot of the times when you’re at a club, you’re already with friends, which also makes it a lot easier. Even if you’re not, most clubs have a bar that you can sit at. Even if dancing is getting too much and you want to go sit at a club instead at the bar, at the club, that’s a great way to meet people too. I’ll say when you’re interested in going home with someone, I’ve been discovering a new side of getting to know people in that way. I think it’s more physical. You start dancing with someone and then the dancing leads to kissing and the whole thing, right? I think being open and doing your own thing at the beginning of the club is how you attract people. It’s a different thing. It’s less words at the club when you’re trying to get laid and it’s more just attracting, where it’s like dancing with your friends, doing stuff like that. Whereas, I feel like when you’re at a hotel bar, it’s more calculated and conversational.

J: Well, yes. That makes sense because it’s a physical connection versus a mental connection.

T: Yes, it’s been crazy to balance both. I’ve had a lot of club kisses recently.

J: That’s very fun.

T: You’ll always see me making out with everyone at the club.

J: Wow.

T: I love making out more than sex.

J: I think I sometimes enjoy flirting more than sex.

T: Yes, definitely. Gets me off.

J: Flirting is not as good as the best sex I’ve ever had, but flirting is better than a lot of sex I have.

T: Let’s be real. Most of the time the sex is subpar.

J: The part that’s more exciting is the flirt, I don’t know, because as a gay man, we have — I don’t want to say we because I’m not speaking for all gay men. There’s a lot of app hookups and sex that’s very casual. My mom listens to this podcast.

T: Oh, my gosh. Hi, Mama.

J: There’s a lot of using apps for these very transactional interactions a lot of the time. For me, when it is something that comes up more organically in real life where there’s the flirtation before there’s sort of, “Is there a vibe here? Are we going home together?” That is all so exciting. By nature of that, you can’t force it. Sometimes you just don’t — the guy’s not there, sometimes they’re not there, and sometimes they are or whatever. It’s like that is so much more exciting to me, that part of it.

T: Oh, it’s like Christmas. Christmas sucks once you’ve already opened the presents. It’s like the anticipation is so fun, “What’s going to happen?”

J: “Fine, I’m just going to go eat some ham.”

T: “Fine. Have you watched “The Grinch” for the 10th time?” No, I feel like it is the fun part. I think flirting is really an art, and I think it really comes from a place of confidence. The key to being good at flirting is not being afraid of rejection.

J: I would just say, but also seeing rejection and knowing when you’re getting rejected.

T: Yes. Read the room. If you’re flirting with someone and they’re giving you one-word answers, or they’re looking at their phone? Run. There’s always someone else out there.

J: Move on.

T: Move on. I think, no matter who you’re dating, what you’re doing, if you’re hanging on to someone that doesn’t want you, that is the worst thing you can do for your confidence. If you’re knocking at a door when no one’s home instead of knocking on a new door, that is actively making you a more insecure person. I think we all have to actively protect ourselves and our confidence because it takes a f*cking long time to build your confidence, and it takes 10 seconds to destroy it. Takes one toxic person to really just run you through the mud and you’re back to square one. I think it’s super important to always, whether you’re flirting, going to the club, going on a date, or if you’re in a relationship, ask the question, “Am I being valued in the way that I deserve?”

J: Totally. Wow. You’re f*cking good at this. I’m very impressed.

T: You want to have a session? You want to be a client?

J: I’m not quite there yet.

T: You’re single now, you need some dating advice?

J: I haven’t announced that I’m single yet.

T: Oh, I’m sorry. Cut shot.

J: No. It’s fine. Just navigating how I’m going to handle that.

T: Cut.

J: No. Instead of booking a session, I like to end every episode with planning our night out together.

T: I love it. Okay, what are we doing?

J: I feel this is very self-serving. I want to go hang out with you and your hotel bartenders, I want to meet some of your hotel bartenders.

T: I love it, but then we can go to The Rosemont or we can go to-

J: Yes, let’s do that. Let’s have some nice cocktails at a hotel bar

T: Then go dance.

J: Then go dance and drink some mixed drinks.

T: Absolutely. That was the first place I ever did a show at the Rosemont.

J: Oh, nice.

T: That was my first booking as a singer.

J: I love that. That’s iconic.

T: Literally, when they first opened.

J: That’s iconic. Well, then, let’s do that and let’s see if they’ll let you get back on stage.

T: Okay, let’s do it. Hotel bar to The Rosemont.

J: Maybe a hotel bar too. We’ll do a Manhattan one, a Brooklyn one, and then Rosemont.

T: I love it. Wait. What’s our middle-?

J: Wait, if you’re going to show me a hotel bar in Manhattan, what would you show me?

T: We’re going to the Hotel Chelsea Bar.

J: Okay. Sick, love it.

T: That’s it. It’s super-old school in Taunton, and I love it.

J: Love. Then we can walk down to the aisle. We’ll shoot over.

T: We’re on our way.

J: Do you have a Brooklyn hotel bar?

T: Let’s see. Brooklyn hotel bar. I don’t have a Brooklyn hotel bar.

J: Then let’s go get one together.

T: Hotel Delmano is nice.

J: Okay, let’s do that.

T: It’s not a hotel, though.

J: It says hotel, means that-

T: Yes, it does. It works.

J: Okay, great. We’ll do that and then we’ll finish at Rosemont and we’ll get them to let you sing.

T: Iconic. It’s done. I can’t wait.

J: Perfect. Thank you so much. This was so fun.

T: Thank you for coming.

J: Bye.

T: No, I’m sorry. “Thank you for coming.” I’m so used to doing my podcast, I’m like, “F*ck.”

J: That was so fun.

Thank you so much for listening to “Going Out With Jake Cornell.” If you could please go and rate and review us on whatever you’re listening to this on, that would be really gorgeous for me in a huge way, so thank you.

And now, for some credits. “Going Out With Jake Cornell” is recorded in New York City and is produced by Keith Beavers and Katie Brown. The music you’re hearing is by Darbi Cicci. The cover art you’re probably looking at was photographed by M. Cooper and designed by Danielle Grinberg. And a special shout-out to VinePair co-founders Adam Teeter and Josh Malin for making all of this possible.