Going Out With Jake Cornell: With an Older Man (w/ Serena Shahidi)

In this episode of “Going Out With Jake Cornell,” host and former NYC hospitality pro Jake Cornell speaks with New York-based comedian and TikTok creator Serena Shahidi (also known as @glamdemon2004). They chat about having gay therapists, how meeting people at a bar is better than the apps, and why it’s better to date an older man. Tune in for the full conversation.

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Jake Cornell: I’m excited to have you on for a litany of reasons. This show is obviously about going out. It’s in the title, and I think going out is something that you clearly enjoy doing.

Serena Shahidi: As often as possible, yeah.

J: Same, truly. What I think is interesting is that you are a bit younger than me.

S: Thank you.

J: I haven’t had a chance yet to talk to someone on the show who is decidedly younger — Gen Z — and talk about what your experience has been like. How long have you lived in New York?

S: Four years.

J: Okay, so you’re finishing out your first four years. I feel like that’s your big adjustment period for New York, especially those first two. How you go out and finding your places to go out and doing all of that, especially when it’s the first place you’ve lived outside high school or college or whatever, there’s so much that happens in that period of time. And I feel like you just went through that.

S: Oh, absolutely. It was big. I moved from North Carolina. That’s where I went to high school. When I moved here, I was immediately a manic person. Oh my God, people are attracted to me here and there are cool places. Neither of those situations existed in North Carolina, so I was going cuckoo.

J: Yeah, I’m from Vermont, so it was the same thing. There’s no gay people and there’s one cool bar to go to. And then all of a sudden I was in New York and it’s zero to 100. I would guess based on the couple of times we’ve interacted that you are similar to me in the sense that you thrive in an environment that’s like getting thrown into the pool and learning how to swim. At least that’s how I am, very much. I don’t want to go to a ton of swim classes as much as I want to just get thrown in and figure out how to do it.

S: Exactly. Socially, I love to be in super-different environments. The weirdest possible, preferably. I don’t know, I like stories and collecting them.

J: You said you want to do it as much as humanly possible. What does going out mean to you? When you wake up and you think about going out, what comes to mind?

S: The thing is, it’s so dual for me because I keep my dating life and love life very separate from my friends. You can see it very clearly in who I date versus who I’m friends with. I am friends with cool people and comedy people and gay people. The people I date definitely tend to be like, “I work in fin tech and I’m twice your age.” So to me, going out either means bar hopping downtown and going out in Brooklyn with the girlies, or conversely, it’s going out with a middle-aged man.

J: There’s a glamor to that, for sure.

S: For sure. It’s a delicate balance.

J: I really love this. I’m not that much older than you, but I used to very much be the same way. I’ve had a boyfriend for five years who is the same age as me, but before that, I often would keep my dating and my social lives very separate. I remember when Hinge first hit the scene as one of the dating apps — do you know how Hinge used to originally work? Because in my mind, it was the most deranged thing in the world.

S: I don’t think so.

J: The original premise of Hinge was that you would only be shown people to swipe on that you had mutual friends with on Facebook. That’s my nightmare. Why the f*ck would you do that?

S: I want to avoid those people at all costs.

J: I downloaded it because I was like, “Oh, new fun dating app.” You’d be swiping, and it would be a picture of me, and then under it would list all of our mutuals. So then you would be like, “Oh, he’s friends with this person, this person, this person.” This is hell on earth, I never want to do this. And I deleted the app immediately.

S: That’s terrible. Raya does that if you have the same contact in your phone with someone, it’ll show it. That’s someone I went on two dates with, I don’t need them to know that I have that contact saved.

J: There’s an anonymity that I would like to prefer at all times with stuff like that, that Hinge used to really just sandbag.

S: That sounds terrible. Yeah, I try to keep things separate for the most part. Getting followers on the internet has definitely made that more difficult because now regular people can sometimes know who I am. I met a doctor while I was out and he had read an article about me and I was like, “What the hell?” He’s not a guy that’s in any social scene that I’m affiliated with.

J: I would imagine it’s hard. It’s one thing to get recognized when you’re out with the girlies, that can be fun. But you can’t really wear a sign on your back when you’re on a date that’s like, “Leave me alone. I don’t want anyone to recognize me.”

S: It is weird when I’m out with an older man and someone’s like, “Are you the girl from TikTok?” Oh my God.

J: I’m curious, because you keep those things separate and because you have that affinity for an older man as one of the things you’re into. If you’re out with the girlies on a Brooklyn night out, are you like doors up, we’re not flirting, if someone makes a move, or closed off to that because we’re with friends? Or are you still open to what might come your way?

S: Oh, I’m open to it. I tell this story all the time of Vincent. We both know Vinvent, of course. The night we went out for one of our friend’s birthdays, the next morning he was like, “I’m sober. What happened that night?” I remember it because we were out in Brooklyn, and normally I would never meet a man in that type of environment. But I had many a drink and we were walking from one bar to the other. I accosted this man who was standing outside the next bar. Basically, I was just like, “You’re coming in with us.” And I introduced him to my friends and I was just like, “This is my boyfriend. This is my new boyfriend. What’s your name?”

J: I love that, that makes me. That’s just a good night. You sometimes need that one little, really assertive move to add some spice if things are starting to flatline a little bit. And I love that.

S: Exactly. You need that. There were many an assertive move made that night by both me and Vincent. In many socially — I don’t know — uncomfortable ways, which is probably why he’s no longer drinking.

J: So would you say you are someone who is good at going out?

S: Honestly, no.

J: I love that.

S: It takes so much energy. I would say I’m good at going out for the average person in America.

J: Living here and going out at all, you’re already in the top 10 percent of America.

S: Exactly. But in a lot of my social circles, if you can’t party until like 6 a.m., then you can’t really keep up.

J: Yeah. Are you someone who can get that late or are you like, “No, we’re going to bed?”

S: I’m going to bed.

J: 6 a.m. is really not an option for me. That is happening maybe once a year. I can do 3 a.m. or 4 a.m. every now and again. But 6 a.m. is really tough for me.

S: Yes, it definitely depends. What are my plans the next day? Is there food available? Because if I’m not eating and I’m just drinking, let’s do 2 a.m.

J: Oh, 100 percent. For anything after 2 a.m., I’m really only interested in a 24-hour restaurant or a diner. I’ll do that and then we’ll get a car home. That’s absolutely gorgeous.

S: For me and my best friend, that’s our move. We leave a party and go to a 24-hour diner.

J: What are your 24-hour spots in New York?

S: Remedy for sure. I’m in Midtown East, so I go to a few other spots. I don’t even know their names.

J: Have you ever done L’Express?

S: Where’s that?

J: I want to say 20th and Park. It’s right above Union Square. It’s a very fun, 24-hour spot. You’ll get some fun celebrity sightings there. I’ve definitely been there at like 3 a.m. and had dinner next to Amanda Lepore. It’s very fun moments like that. And it’s one of those places that’s French-designed and inspired. It’s supposed to feel like a 24-hour Parisian restaurant, which makes it feel kind of nice. But then you are also like, “Oh, this is ultimately a mid-level restaurant, but something about it feels luxurious just because it’s French-themed and the lights are dim.”

S: I love a tacky, fake classy theme. I love that. My ideal restaurant aesthetic is The Cheesecake Factory. Not food-wise, certainly not calorie-wise.

J: No. But I get what you’re saying. I am a little tired of the minimalist New York aesthetic. The very clean lines, everything is incredibly monochromatic. I’m down for a little bit. I want a little bit more excess. I want some maximalism.

S: You know what I’ve been oddly obsessed with recently? The aesthetic of Joan Rivers’ house; a Vegas, gaudy mansion, faux-Mediterranean? Just gaudy, I love it.

J: Like the Venetian. I know exactly what you mean. Have you been to Vegas?

S: I’ve been to Vegas once, yes.

J: Were you an adult or were you a kid?

S: I was 19. I was there with my suitor at the time who was an adult.

J: Incredible.

S: Yeah, it was fun. I did take my first — and only, actually — legal edible, and it was so much for me. I definitely cried.

J: Yeah, that’ll happen.

S: I wasn’t even feeling emotional. It was just that suddenly water was pouring out of my face.

J: Totally. I do love Vegas. I’ve only been once, but I’m making plans to go back soon. I want to see Katy Perry. But I went there for Gaga three years ago and it was like heaven on earth. And I do think you can only be there for 48 hours to 72 hours maximum.

S: Yes.

J: I do think I would have really been in a bad place had I used marijuana at all. I don’t think that would have mixed well for me. It’s definitely a drinking spot for me. I just can’t handle that much stimulation. When you’re drinking, having a little bit of a dark side is sort of fun. But when I’m stoned, if things have a little bit of a dark side, I’m like, “No, my soul will get corrupted and I will go to hell.”

S: Yes, absolutely.

J: My upbringing starts to creep out via the THC.

S: Ohh. Yeah, I’m not the biggest weed person. So I feel like that was definitely a mistake, especially in that context. But I love how Vegas feels like you’re in a board game.

J: It’s Disney World for adults.

S: Yeah.

J: But you know, everything is fake. Everything is nice but cheap, and nice but tacky, and I do kind of love that.

S: I love that. I definitely want to go back. I was watching that video of Katy Perry performing with the big toilet.

J: It’s going to be a good f*cking time. Do you know what I mean? I like a lot of her songs.

S: Is this the Katy Perry renaissance, because she did dye her hair back to dark?

J: Yeah, I think that people are coming around. You got to show respect. You can all make fun of certain things, but the songs are the songs and they hold the f*ck up. She was a time, you know?

S: Absolutely. I think it can come back. I’m ready to be a Katy cat.

J: I think part of me has always been a Katy cat, but I haven’t ever taken it on as a fall moniker. But I could be into it. I’ve never seen her live, so I think that would be fun. But I do like a lot of her music. So walk me through this. You have two versions of nights out. You have nights out with the girlies. You have nights out with the suitors. I’m obsessed. When do you decide which one you’re having on a night? What are your preparation differences? What are your goals? And what does the ideal version of each of those nights look like for you?

S: Yes, OK. Usually, nights out with the girlies are more spontaneous. If my friend is like, “Let’s go out tonight,” I’m not going to be like, “You should have given me further advance,” in the way I would be with men. Just because I’m a b*tch. It definitely depends on who I’m going out with, but I love to do a little downtown moment. Where do we even go? I haven’t been out in the past few weeks.

J: Well, it’s been a hard month. It’s been hard.

S: Yes, this past month has been rough. I stayed in New Year’s Eve because I had a sore throat and I was convinced. We’ll do bar hopping, maybe go to a Susanne Bartsch party. I have found someone who works in PR and is always going to those nights. The outfits are wilder, the hair and makeup is more experimental. Whereas going out with a suitor, I’m more likely to be in a little black dress with a cat eye and a red lip.

J: Totally.

S: That’s probably going to be at a restaurant or maybe a hotel bar or something like that. Definitely a hotel bar if you want to pick up rich men.

J: Yeah, and that’s my next question that I was curious about. Do you prefer a pre-arranged date from an app or do you prefer going out and finding something?

S: Definitely going out and finding something.

J: I think you’re a really rare breed for that, especially these days. And I really respect the hell out of it.

S: Do you think people really prefer that, though? Or is it just easier?

J: I think they prefer it because no one knows how to be comfortable. I know people that won’t go to a bar alone, they won’t go to a restaurant, they won’t go out to dinner alone, they won’t go to a bar alone. When I started going out, it was when I lived in England and I was 19 and there weren’t apps yet. This was 10 years ago. So I had a phone that had Bejeweled on it. But that was it. There wasn’t the app option. So you go out. I think it would have been easier back then because that was true for everybody. I think Grindr had just started, but it was still a niche thing to be on Grindr, even among the gays when it was that early. But it was that anyone who’s single and looking to meet up and hook up, they’re all out at the clubs and the bars. Where now I think there’s less of that because that has been relegated to apps. So now people are afraid to do it. But I think it’s a really important art form, and I’m really thankful for people like you keeping it alive.

S: It is an important art. I feel like charming men is truly a lost art that I want to bring back. But I don’t know, dating on apps is difficult for me because I have trouble caring about men.

J: They’re not real until you meet them in real life.

S: Exactly. So I am horrible at making plans or replying to them because it’s like they don’t exist in my head. This Hinge match, who cares? Whereas even if I met someone briefly at a bar, I got the energy. You read off of them, whatever. I’ve also gone on plenty of dating app dates where it’s not necessarily that they’re a catfish or anything like that, or something terrible comes out about them. But you walk in and it’s like, “OK, you look like your pictures. Nothing surprising, but still immediately. No.”

J: That’s what is behind what I’m talking about with what this lost art form is. It’s also a loss for that appreciation of that moment when you’re out and someone catches your eye and you’re like, “You’re coming in this bar with me, you’re my boyfriend now,” That feeling you get when you start a spark like. I hate saying spark because it’s not even sentimental or romantic. It’s something more of a sex thing than it is a love thing. But just that thing of being like, “Oh, I could be down.” And then also seeing, “Oh, you’re into me.” Doing that part online, at times, is like you’re skipping one of the best parts.

S: Yes, it’s so much more exciting in person. Whereas online, you set up a date and then you have to convince yourself to like that person.

J: I met my boyfriend on Tinder, so I’m not saying it doesn’t work by any means. I am a Tinder success story. But people should not totally write it off the in-person because I think it does have a power to it that can’t be replaced.

S: Yeah, I would say dating apps: optional. I could take them or leave them. But going out in person is a must for sure.

J: I am envious of the hotel bar move. The fantasy of putting on a cute dress and doing my lips up to go to a hotel bar and see what happens. I will tell you, I was a hotel bar bartender for a year or six months, and it didn’t occur to me when I took the job. Which is stupid, but I was 22. It didn’t occur to me once, “Hey, what do you think’s going to happen if you bartend in a bar where half of the people there have a bed upstairs?” It was debaucherous. The sh*t I would see was wild.

S: Oh, sure.

J: The number of covert wedding ring removal and then someone coming in, seeing them meet for the first time and start flirting and then hook up and go upstairs together. It was a lot of that. A lot of like, “Hey, you have to go upstairs now because what you’re doing in this bar should be happening in a bed.” Full-tilt, people feel like it’s their house. It gets raunchy. But it’s also crazy because it was a nice hotel. So everyone looks amazing. Everyone’s drinking Moët. It’s elegant and gorgeous, but everyone’s acting like trash.

S: Yes, it’s definitely elegant debauchery vibes.

J: That sounds like a good band from 2009.

S: Yeah, that sounds like a good band I should start now. I was out actually with my friend a couple of weeks ago, my friend Marlowe. Shout out, she wrote a book called “Happy Hour” that’s about two girls going out and all that. She’s a fantastic writer. But we were at The Mark and we met this old rich dude who immediately gave each of us $300 cash. I don’t even remember the context. But we sat down with him and talked to him. At one point, Marlowe saw garbage men stopping by, and she was like, “Wait, can I have another $100 to give to them?” And she literally ran out and tipped the garbage guy.

J: I’m obsessed with her.

S: She’s everything.

J: Incredible. You’ve lived in New York for four years. You moved here right from high school, right?

S: Yes, I moved here after school.

J: I would say you’re impressively far along for being 22, after four years in New York. In terms of knowing the spots, having sh*t together and knowing what you like. This is not where I was when I was 22. What did those four years look like in New York? Did you hit the ground running? How did you get where we are today?

S: I mean, I definitely hit the ground running when I first came to New York. I’ve never experienced all of this culture and social life. So I just wanted to experience as much as possible as intensely as possible. I definitely went on three dates in a single day. Or I would go to random parties. I went to an NYU frat party just because I was like, “This sounds like something I would never do. So let’s check it out.” Just being a yes girl.

J: Were you a yes girl before in North Carolina, or did New York bring that out of you?

S: There was nothing to say yes to North Carolina.

J: I guess that’s kind of the same as me. That’s kind of how I feel. I felt like I never had a chance to say yes, so when I got to the city, I was like, “Let’s f*ckin go.”

S: Especially in my high school, there was a party scene. But it was either that you don’t party at all or you do heroin. I’m picturing the James Franco-directed “Palo Alto” movie.

J: I definitely had the same thing, but more so in college. In Burlington, there was the bar scene or the party scene. I was like, “Hey, guys, like, I don’t know who wrote the book on this, but I just don’t think it’s fun to be in a basement with 600 people.” I love a bumpin’ party, but I used to say that the theme of the party is, “If there was a fire, we wouldn’t get out.” We would all die. I don’t want to go to that party. If that’s the theme, I’m not going. I think it’s interesting that you learn a lot about what you do like from what you didn’t like from before.

S: Yeah. What was the crowd like in the basements?

J: I went to UVM because it was my state school. It wasn’t a good fit for me, honestly. I made friends there and some of my absolute best friends are from there. But was it the right fit for me? No. The party scene was a weird mix, because it’s people from Vermont. So there’s a lot of lower-middle-class and working-class people from Vermont who go there because it’s a great public school, but it’s our state school. We get in-state tuition or whatever. And then it’s a lot of kids who come from the Connecticut, Boston, New York area and vacation skied in Vermont. And they come from a sh*t ton of money, and probably more new money. They’re not the old money people who had to go to Yale or it was a humiliation to the family. They had money, they would go skiing. I remember one girl my freshman year, her dad was the owner of Kraft Mac & Cheese. That sort of vibe.

S: I love it when someone’s the heir to some random sh*t.

J: Especially when I was doing comedy at UCB, you would find out that their parents were rich and the ways that they were rich were always my favorite thing in the world to find out. But the thing about UVM was that it was all of these rich kids from very affluent backgrounds, but they’re all doing steezy, crunchy, salt-of-the-earth, backwoods Vermont drag. They’re wearing sh*tty corduroys and hiking boots and an old flannel. But their dad is a cardiologist that lives in a penthouse. It’s very funny. But the parties were just very heterosexual and had a lot of kegs of sh*tty beer and very crowded basements. It was better once we turned 21, you could go to the bar scene. There were still bars that had that vibe. But then there were cocktail bars and stuff like that. Those were a little bit more like my scene and where I found my people and my vibe. And then I just followed that even more when I got to New York.

S: Do you know what I just realized, like yesterday? When this pandemic started — this is kind of random — but I was still using a fake I.D. I was still 20.

J: That’s so funny. Damn.

S: So I’ve only been legally drinking during this pandemic. Granted, I got a lot of illegal drinking.

J: But yeah, we all did. I had such a good fake I.D. in college. It was my crowning achievement. If you had to say, what is something you’ve learned from these years of finding your passion and going out and honing your craft? What are some things you’ve learned?

S: What are some things I have learned? I’ve spent so much of my time going out and I’m like, “Have I learned anything?” I destroyed my body. I mean, it’s hard to say.

J: I guess I’m just impressed. Especially if your taste in men is older fin-tech people, you’ve got to be really discerning because there’s a lot of hellscape monsters in those populations and in those spaces where those populations hang out. Maybe you just have really good instincts or you’ve figured out your own way to suss out how to get through those situations.

S: Oh yeah. I mean, I have a million ways, just because I’m very quick with men. I don’t like that. Don’t say that. I remember, I was talking to a guy on some dating app recently. He was like, “I live in the Upper East Side” and I was like, “Oh, I’m in Midtown East, right below you.” He was like, “Oh, I like the idea of being on top of you.” I was just like, “Don’t talk like that. It’s unbecoming.” No, I don’t think so.

J: I’m envious of you. I’m someone who’s deeply conflict averse and you seem like someone who is pro-conflict. Or confrontational, at least.

S: I’m like that in my dating life, but kind of nowhere else. Maybe I’m just mad at men in general, so I feel like having conflicts with them.

J: That’s so refreshing because I can’t tell you how many friends I have, especially their girlfriends, who are totally the opposite. They’ll be so assertive and know what they want in their career better. This isn’t even just women. I have guy friends that are like this, too. They are so assertive and know exactly what they want. And then like when it comes to dating, they’re like, “Um, like me.” No, you have to show up with that same like “oomph.”

S: I know, it’s so weird. I’ll have friends who are wildly successful in their career and then they’ll be like, “Wait, can you read this text and tell me if you think this guy likes me.” I’m like, “What in the world is happening?”

J: I’m glad you brought this up because I’ve been saying this for years. The syntax of a text message is not what’s going to make or break it. I have one dear friend who would always make me read his text messages. And one time I was like, “Babe, if they like you, they’re going to text back. And if they don’t, they won’t.” That period versus exclamation point is not what’s going to happen. If you’ve already gone on a date, they know whether they felt something in their lower stomach or not. They know whether they felt something. They’re going to follow that, not the syntax of your text so you need to chill the f*ck out.

S: No, it’s true. I’ve never understood that. I don’t put a lot of thought into texting. I also don’t love communicating that way if I can talk to someone in person. I’m not a “send me a good morning text” type of girl.

J: Back when I was dating, if I ever got a good morning text, it’s over.

S: I feel like that’s one of those things that became a thing on social media. And now everyone’s like, “Oh, it’s that cute thing to do to send a good morning text.” No, it’s just what children tweet about.

J: Let me miss you. Let me want to see you next time.

S: Also, I wake up at noon. So your good morning text is not even applicable.

J: You missed it.

S: Yeah. I don’t know mornings.

J: I’m having Panera, it’s lunch. So sorry.

S: I’m having a sandwich.

J: Do you get told a lot that you’re wise beyond your years, like an old soul?

S: Yes, by plenty of old men I date.

J: Sure. Has that always been your taste? Older guys?

S: Definitely when I moved to New York. But I also didn’t really date in North Carolina. I had one little boyfriend who was this little skater boy with fluffy blond hair. We would play MarioKart or something. It was just very that. I moved to New York and I kind of familiarized myself with the types. To me, there are two major types of men to date in New York. There’s the younger, creative guys and the older finance, tech, health guys. I moved here and I was like, “OK, I met the Timothee Chalamets of the world, and I’m going to have to pass.”

J: Because the thing is, the younger tech guys are obviously in New York. But in my experience, they’re working 100 hours during the week and then doing a lot of coke on the weekends.

S: Absolutely, the analysts and finance boys.

J: They’re analyzing lines of coke. That’s what they analyze.

S: Yes, they are.

J: But then you come in when they’re a little bit older and they’re starting to mellow out. And I do respect that because they have that energy of partying, but they also are slowing down a little bit.

S: Yes. I gotta respect that they work hard and play hard, in general. The things I have seen men like that do and they get up at 7 a.m. and go to Barry’s Bootcamp. Holy shi*t.

J: Yeah, it’s actually truly a wild breed. I didn’t understand it until I started bartending in the spots in New York where those kinds of guys go. You would not believe how much of financial and corporate America work is being done fully drunk. I didn’t know this. Before I moved to New York, I thought they were alcoholics who are a rare breed that are secretly drinking and it’s a private shame thing. It’s a big secret that they’re drinking too much. And then there were people who didn’t have a drinking problem. And then I’m bartending in New York and I’m bartending at a lunch meeting where they each had three Martinis. Then they’re like, “OK, cool. Good deal.” So a $150 million dollar deal was signed, sealed, delivered at the bar, three Martinis deep. And then they’re like, “I got to go back to the office. I have two more meetings.”

S: That’s the crazy thing, it’s important people doing sh*t like that. You expect it to be the intern or the temp. No, girl, it’s the M.D.

J: It’s the M.D. The VP’s are getting ripped. I watched people expense a $1,000 bottle of wine on their corporate card at a lunch. It’s insane.

S: There was this guy I was dating who was like, “Oh, I work better when I get drunk at lunch.” But I do respect it. I had maybe one year of my life when I was F.I.T. I could party until 4 or 5 a.m. and then go to a 9 a.m. class. That was the peak of my ability to live like that. It did not last long.

J: That’s something I’m navigating now that I do comedy full-time. I used to be someone that really preferred to keep work and play separate, especially when I was working restaurant jobs. I’m not trying to get drunk at work and I’m not trying to get drunk after work often. Because I need to save my energy for comedy stuff and my career outside of that and also just my social life outside of work. I don’t really want them to bleed in. Obviously, I’m not really drinking for the podcast episodes. But when I do shows and when I do gigs at night, it’s with my friends. It’s at a bar. The work and the pleasure starts to mix. I have friends that are like, “Oh yeah, I prefer to have two drinks before I go onstage.” That’s not me at all. I totally respect that. But it is a weird navigation where, if you’re at the show for two hours and you’re up whenever, I’m always like, “Can I go earlier?” It’s just interesting to see how everyone balances things out.

S: It’s such a strange balance. It’s like a lifestyle interruption. I was literally telling gay therapist…

J: Shut up, you and my boyfriend both have gay therapists and I’m so jealous.

S: Oh my God, literally slay.

J: I’m going to get one. I’m currently doing the thing where I have health insurance that I pay so much money for that covers nothing. That’s what I’m doing right now. Live, laugh, love.

S: But I was telling him the other day that I know I could never work a desk job. That’s not the life for me. But I’m so jealous of them because their day-to-day lives are so simple, they know exactly what they’re doing. They get up early because they have to. I’m not even getting sunlight half of these days.

J: My boyfriend and I were talking about this recently because he’s also going through a career change. This is something an older guy told me when I dated an older guy when I was younger. This is disgusting that he said this, but it’s true. He was, “Any job you have will have a sh*t sandwich that you have to eat to do it. And you just have to find the one that has the sandwich you’re down to eat.” Why it had to have like sh*t involved, I don’t know. But it’s true. No job is perfect, even your dream job. People say, “It’s perfect. I’m never not happy.” No, there’s definitely part of your job that you don’t want to do. Having a really traditional day job, any of us could go sign up, get the money together, and go do coding school or UX design school for six weeks. In a few years, we could be making good money. But for 45 or 50 hours a week, you’re going to be doing this thing that is not passionate or exciting to you. And there’s nothing wrong with that, but is that the sh*t sandwich that you’re able to eat? That would spiral me into a really hard depression. I don’t think I would do well with that.

S: Yeah, I would slowly go crazy.

J: But like some people can, God bless. It is nice that you know exactly where your health insurance is coming from, exactly how much money you’re going to make this year, and what the parameters are for your time off and when you can do things.

S: I do think if I was a different person, I might be doing some sort of finance thing. Even when I’m like, “Oh my God, I wish I could do that,” I would go fully insane. Like Joker, insane. What am I talking about?

J: Yeah, I also think I’m so all or nothing with things. Being a creative and having a creative career, you have to put in so much to get so little back and that’s fine. I do think that if I were to become a finance person, at this point I would be trying to become Jeff Bezos. The way that I would be evil, I do think that that’s where I would go.

S: I don’t blame people like that at all for being the way that they are, the greed and all that. It would be pretty easy to get sucked into all of that, especially when you’re drunk and coked out the whole time.

J: I know, right? I haven’t talked to anyone about this yet. Did you see the photos of Jeff Bezos where he’s hot and he’s getting hosed down? Did you see this?

S: He was not hot. Oh my God,

J: He’s ripped, he’s buff. If it wasn’t the man who has the capability of solving climate change with a phone call and is choosing not to do it — obviously he’s evil — I think people find him unattractive. But that body type is hot to a lot of people, he’s in good shape.

S: Can I say something homophobic?

J: Yes, always.

S: Gay men are always like, “Oh my God, this guy is hot,” and he just has abs. That’s literally it.

J: When I say hot, I don’t mean I’m attracted to him. I mean that he’s in good shape. Someone could look at that body and say, “He’s hot.” I don’t find Jeff Bezos attractive. I also am not an abs guy. It’s not my thing. This is all to say that if I had the money and power that Jeff Bezos did, can you imagine being like, “I got to stay in shape?” It would be so low on the totem pole.

S: Yeah, that does take a lot of time. I don’t know, maybe he’s buying a lot of flat tummy tea.

J: I think I would just be like, “Look, I’m going to really live my life and I’m going to ride this body hard.” I would put millions of dollars towards, when I’m 60, cutting the head off of an Abercrombie model to stitch me on that.

S: Yeah, it’s always blown my mind that he never got hair plugs. That’s one thing I respect about Elon Musk. He was balding. He was like, “I got the money to fix this.”

J: I didn’t know about Elon, and someone showed me a before picture and I was like, “Oh, he was Gollum.”

S: It’s so crazy. He’s not busted now. It depends heavily on the picture. It was looking rough back then.

J: I would go for Jeff before I went for Elon, visually.

S: Really? I think I would go for Elon. OK. If he went for Grimes, he would go for me.

J: Oh, 100 percent.

S: An insult to myself.

J: I actually can’t imagine a more miserable conversation than a conversation between Grimes and Elon Musk. If I got stuck at that dinner table, like Azealia Banks did, I would absolutely die.

S: My God, they were definitely talking in code and probably mouth sounds. I can’t imagine.

J: It’s a hellscape. That is true what you said about gay guys just seeing abs and thinking someone’s hot. But it’s because of the pressures to make our bodies perfect that we put on ourselves toxically. When anyone achieves anything like that, we’re like, “Ugh.”

S: That’s true, it’s considered so synonymous. Whereas girls are like, “He has to be sensitive. He has to have read this book.”

J: Are you an outlier among your friends with your taste in men and also liking to go out in the ways you do? Or do you feel like you’re in sync with everyone?

S: I’m a bit of an outlier. I feel like I’m also rubbing off on some of my friends.

J: Because they see you at restaurants you get to go to.

S: Exactly. If you stop dating boys who skate, you can do it, too. Most of my friends are in their 20s and they tend to date guys in their 20s. Which is fine. Do you know who texted me earlier today, and was like, “I want to set you up with someone?” It was Caroline Calloway.

J: She texted you and wants to set you up with someone? Oh my God, Is it someone your age or is it someone older?

S: He’s in his 20s. But the thing is, he has an ex that’s famous. And I’m like, “Why would he want me?”

J: Are you friends with Caroline Calloway?

S: Yes.

J: Gorgeous. If a friend knows you and you can trust them, I’d say go on the date. Unless the ex is fully scary.

S: Oh, definitely not.

J: I love that. We’re coming to the end and I do find that I’m really enjoying this conversation because I do think you are a preserver of some things that were really put at risk during the pandemic. As New York is changing and shifting, it’s really nice to see that that stuff is being kept alive. If you had to give advice to someone who is wanting to come to New York and find their vibe in all of this stuff, in going out in navigating being in your early 20s and moving to New York, what would you say?

S: I would say definitely experiment with different crowds. Social scenes are always changing. You never know who you’re going to meet or what sort of thing you’re going to like. I would say there’s a lot of artifice everywhere, but especially in big cities like New York. Every poor person is pretending to be rich, every rich person is pretending to be poor.

J: So fucking true.

S: Don’t believe everything that people tell you about who they are or something like that.

J: Don’t let people tell you who they are, they’ll show it. If someone’s telling you who they are, it’s not worth it. It’s not real.

S: They will give you $300 at night.

J: They’re not stylists. I went through a period where everyone’s like, “I’m a stylist.” No, you’re not.

S: You got dressed this morning, it doesn’t mean you’re a stylist. Don’t be afraid to go places alone and just look around.

J: Don’t be afraid to go places alone. I think what you’re good at that I wasn’t good at when I was younger that I’m hearing, is taking the risk of doing something you’re not going to like and being like, “OK, not doing that again.” Be willing to have a few bad nights to figure out where the good nights are. When you’re young, time is on your side. It doesn’t have to be perfect tonight. It can be perfect tomorrow. You’re going to find out what works out, but you gotta try everything.

S: Exactly. That’s when you get the funniest stories. I used to hang out with my friend and she had a sugar daddy, and he and his old friends would invite us to spend hours just drinking wine and stuff. It was just the craziest experiences and stories from that group. It was so funny. Sh*t like that where it’s like, just say yes. Why not?

J: Yes. And also, I love that you always fall back on a little black dress for the date. I think that’s a good move.

S: Exactly. Get a good little black dress.

J: Well, Serena, thank you so much for doing the show. This was so fun.

S: Of course. Thank you so much for having me on.

J: I’m sure I’ll see you out and we should get a drink sometime.

S: I would love to.

J: Gorgeous.

S: Gorgeous.

J: Bye.

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 shoutout to VinePair co-founders Adam Teeter and Josh Malin for making all of this possible.

The article Going Out With Jake Cornell: With an Older Man (w/ Serena Shahidi) appeared first on VinePair.