Please See Below with Brynn Whitfield
Tight Fives and Red Flags: Dating in NYC With Jared Freid
Wed, 09 Apr 2025
In this refreshingly honest episode, Brynn sits down with comedian and U Up? podcast cohost Jared Freid for a deep dive into modern dating, being the “funny one” on first dates, and what it really means when someone says they’ve “deleted the apps.” They unpack why dating in NYC can be both magical and maddening and how men and women often approach relationships from wildly different emotional starting lines. Host: Brynn Whitfield Guest: Jared Freid Producers: Belle Roman, Chelsea Stark-Jones, and Kat Spillane Editor: Jon Roemer Theme Song: Devon Renaldo Learn more about your ad choices. Visit podcastchoices.com/adchoices
Chapter 1: What does Jared Freid think about modern dating?
I don't want to be shown who I look like. I don't think most people want to be shown, especially on a date, so they're like, oh my God, you have the same... They said you have the same vibe, you have the same this, you have the same... Was it like a friend or a cousin or something? It was like a friend's husband, and then they brought up the picture, and I was like...
Again, I just don't think... This person could be offended that someone thought I looked like them. Again, it can go all ways. It's hard to say that you were like... Again, I just don't want to be shown who I look like on a date. It kind of takes away the special nature of us getting together. I'm kind of like... I brought that to the podcast.
I think that's like an interesting... Like, what would you do? You know, so... If someone was afraid of dating me, I would totally understand that. Like, I'm not for everyone... Just like anyone is not for anyone. Yeah, yeah, yeah. That's a scenario you would have to deal with because... Listen, we all have opinions and we all make judgements, and everyone's judging. No one cares, everyone judges.
So no one's holding onto it the rest of their life, but they go, oh, I got shown what I look like, I don't think I'm gonna go on day two.
Has someone ever contacted you after, even if you did keep it classy and very general? This person. So after you talked about it on the pod, then she talked?
So then I see them a month later, and they're like, so-and-so isn't ugly. And I'm like, what?
Oh my god.
I saw them in person. And they're like, if I showed you Brad Pitt, you wouldn't care. I go, well, you didn't. I was like, that's not how it went. And I would go, I don't look like him. It's a waste of time. Again, that's why dating podcasts are fun. I enjoy unpacking those things. I'm going to give how I feel on it. It's okay for someone to disagree. Yeah.
So, yeah, people – I've gotten messages from people, and I've been at bars. I had another instance where someone was like, you talked about me. And I – again, here's the thing. Men who talk about their dating life – there's not a lot of straight men who talk about their dating life.
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Chapter 2: How does being a comedian affect dating?
Oh my God, I've told this to so many friends. They're like, I think after like three dates... Someone I know, then he kind of was like, hey, I don't think this is going to work out. And then she's like, I was trying to think. Maybe on that second date, he didn't like such and such. And I was like, no, honey. He wouldn't have even gone out with you on the first date.
They ran into each other's street in New York. That's how they met, exchanged numbers. And I was like, he wouldn't have even taken you on the first date. So it wasn't something he was icked out on the second date. Because then he also went on a third date. There's no male physical ick. He thinks you're hot. He thinks you're attractive. That's it.
No, the reasons men end things are way more personal and detrimental. Yeah. Tell us more. That's why the ick is fun for women to talk about and not fun for men to talk about. I talk about the ick on my special.
I know. You're like the inventor of the ick. I'm not the inventor. Do you own the IP of the ick? It's under your name? I wish.
I'm owed a lot of money if that's the case.
Wait, so explain that to me. I love the detriment. I like the way you say it. It's far more detrimental.
Well, because you see, like, you know, maleics are turnoffs. Like, they don't see a future with this person. It's not like, I don't think any man is, like, one, you know, sandals with jeans away from being like, I can't fuck this chick.
Yeah.
You know, like, that's just not how it works.
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Chapter 3: What are the challenges of dating apps?
Oh, we date, I could try this, and then two months in, you're like, I don't want to marry this person. Now you're two months in, why would you make me come here? That gets put on the guy. Now it's TikTok story time. This guy said he could, you know, make long distance work. And then he then we have sex and we hook up and the, you know, the energy changes.
Yeah.
Well, yeah, I got to know you. You know, like it's like, aren't we allowed to get to know someone? And I feel, you know, personally, this is where it's tough to relate to the audience because I do feel and I'm sure you do. You know, a big step for me is like putting someone on social media. And I think that's a big step for everyone. I think we all have 200 friends that are watching.
I think at this age, you're 39. I'm 38. I turn 39 in like a month. Yeah, at this age, I'm done with that. I'm literally going to do one of those announcements. No one's going to know that I'm even dating anyone.
Good luck with a dating podcast.
And I'm just going to put a picture of me with a ring. And then I'll do the introduction.
What are you going to talk about on this show?
Oh, I have like 25 years worth of dating experience.
But I'm just saying, people are going to want to know. And then like, well, here's the other thing. No man in your life is going to care.
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Chapter 4: How do men and women differ in dating expectations?
Yeah.
And they end up putting their life ahead of the life that they might want. And I do this all the time.
I do it nonstop. Right.
It's the story of my life. So I always call it the aunt woman.
Yeah.
Like women who love being an aunt. Yeah. They're so busy with the niece and nephews.
Yeah, yeah, yeah.
It becomes like the ultimate way of avoiding their dating life.
Yeah.
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