Please See Below with Brynn Whitfield
Loading Your Silly Girl Spring With Tiff Baira
Wed, 14 May 2025
Tiff Baira, Gen Z matchmaker extraordinaire, sits down with Brynn to discuss the mess (and the fun) of modern dating. They delve into the importance of staying true to yourself and why confidence is key. If you're gearing up for a silly-girl spring, this episode is your perfect pregame. Host: Brynn WhitfieldGuest: Tiff BairaProducers: Belle Roman, Chelsea Stark-Jones, and Kat SpillaneEditor: Jon RoemerTheme Song: Devon Renaldo Shop for every party at amazon.com/BirthdayCelebrations Learn more about your ad choices. Visit podcastchoices.com/adchoices
Chapter 1: Who is Tiff Baira and how did she become a matchmaker?
Welcome back, loyal listeners. Okay, I'm so excited for today. You are going to love this. I have a New York City darling. You might have seen her on the streets during some matchmaking. She literally makes me look like an old, boring millennial. Flirt. It is the one, the only, Tiff Farrah. Welcome.
Hello, welcome to Please See Below, my brand new podcast all about perfecting the art of oversharing. Here, we mention the unmentionables and talk about topics and things that no one wants to say out loud, but everyone is desperate to know.
Welcome to... when that intro is crazy and not true. Yes, it is.
No, you're the hottest. I'm so pissed I don't have on sequins.
Oh, my God. Trust me. I got enough for both of us.
Okay, I know. You literally do. Next time I see you, matching suits. Okay, okay. Next episode. Next episode. You are literally the woman on the street post right now. You are trending TikTok, Instagram. Everyone knows you. Everyone loves you. You are NYC's Gen Z matchmaker. How did that happen?
A lot of bad fucking dates. I was like, if someone's not going to change this, I will. No, I mean, I've lived in the city for 10 years. And I think you grow and evolve. And you're like, hey, like, I want to date with standards. And I want to, like, make new friends. Like, basically, like, I was finding that it was hard to make connection. And genuinely, between the 4 a.m.
What are you doing text and, like, the bar was in hell. And I'm like, why don't I just create a concept where it's so easy? Just show up as yourself. There's no, like, who pays the bill or any of those, like, insecurities that come up. Let's put a table in the middle of the street and see if people connect.
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Chapter 2: How can dating be made more fun and authentic?
Okay, so dating in NYC got so bad. You're like, I'm going to take this shit outside. I'm going to put on a cowboy hat. I'm just going to set up shop. Or also, because you have two different weekly series. Both are amazing. The other one's like, you're just going to go up to strangers and be like, will you take me on a date right now? Cool.
Like there's some movie character that you remind me of and I can't put my finger on it. It's like How to Lose a Guy in 10 Days meets like the Barbie movie meets Elle Woods.
Meets like How to Be Single. Yeah. No, I love those comparisons. I mean I think the main thing is like I definitely struggled with confidence about putting myself out there and I think before – TikTok, giving advice and all that, you only heard certain narratives that if you don't look a certain way, if you don't lose your whole fucking personality and you're boring, guys aren't gonna like you.
And my whole ethos is like, fuck if they like you, you want them to like the real you. So I feel like with street arts and with Take Me Out, I'm putting myself out there and showing like, hey, you get rejected, but like you can't lose what you don't already have. Like you got to shoot your shot and see what happens.
So it's almost a test for me to grow, too, because it's so easy to be like, oh, my God, guys suck. There's no one out there. Like I'll never meet anyone. But that's like a self-fulfilling prophecy. So when I felt like I was like not meeting anyone and I felt like discouraged, I was like, let me just try. And it's hot to try.
It's hard to try and you're crushing it. Now putting yourself so out there and doing it in front of a camera and then putting it on social media, so does that give you more confidence and then you're less scared of rejection? Or like prior to doing all this and we were just like the rest of us, like at home, dating on the apps or like going out on awkward dates,
obviously it's better the way you're doing it. Because I think some people would see it and be like, it's like watching The Bachelor sometimes when I watch it. I'm like, I love it and thank you for entertaining me, but I don't know if I could actually do it. You know, like I don't even want to date on my show. I'm like, no, thanks. But like, come on, let me help. Brynn. Please help me.
No, I mean, I think what's interesting is that, yes, of course, it's entertaining to watch. But what we try to do, it's easy to make dating shows mean. Like you can make it clickbaity.
Yes.
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Chapter 3: What are the challenges of modern dating?
Some things just don't mix. So I always love to keep it as positive as possible. Like, on the new Take Me Out, I wanted to evolve it even more.
I just saw. I just saw.
It's a different format. No, it's a new format. And it's, at the end, the producers, they bring us separately. So they do a confessional saying if they like me. And then I do a confessional and say if I like them. And I still haven't seen the edits yet. So, like, I don't find out what they say until we post it.
Are you serious? Why are you doing this to yourself? You have executive producer credits. Let me see the footage. And I'd be like, oh, he didn't like me? Then I'm going to rewrite it so I can bash him. Scrap it. Get it out. Delete. Next one.
No, I think it's really interesting. I think putting yourself out there in confidence is a muscle. Of course, these are extreme things, like going on a date on camera. But what I've learned, and especially matchmaking on Street Hearts, is there's so many amazing people out there. And when you put yourself out there and have an open mind,
Saying like, I can't guarantee where this will go, but I know that I'm putting myself out there and that's what's important. Changes your whole dating experience.
And I feel like dating should be more funny. Like dating should be more funny and dumb. Like I just, I started a dating app recently and now it's generated. It has like Gen Z in mind, but obviously we're going to open it up. It's going to be open for everyone. But it's like, my whole thing is like with, you have all these dating shows and you have dating apps and everything's so serious and scary.
Even like, I'm still on Raya. It's so funny. I'm like, have a dating app and I'm still on Raya. I got banned. Oh, did you? We're doing what? Tell me. Tell me. This is going to be awesome. Why did you get banned for violence? I mean, of course I took a few straight shots. Everyone knows you're not just a dude. Everyone knows you have to get your friend's camera.
No, but the main thing. I know. Where were you? Where were you for me?
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Chapter 4: Which NYC bars are perfect for dating?
Oh, like a millionaire will never like you if you're not a size two. You know, or like someone, a high quality person won't like you if you don't look like this, if you don't behave.
It was all about, yeah, it was all about changing yourself. They're looking for someone. Yeah, and sometimes some of those dates, they would be like, I want someone who's working out more. They was all kind of like ripping on each other. Or remember, I actually was watching old episodes of it. The MTV show where they get out of the limo.
Next Bus. Next Bus. AKA my favorite show of all fucking time. Wild.
It's awesome, especially the gay episodes.
No, I need the TIFF bus.
Oh, my God, do it. Wait.
100%.
No, I mean, I think there's something real to honesty, and I love that. I don't think we should hide how we feel, but I think there's better ways to articulate it and also lead from a place of compassion rather than just anger. Agreed, agreed. when you're dating, you can't control how other people are gonna treat you, but you can control how you respond to it.
Yeah, you can always control your response, but I like everything about the content you're doing, because it's about making things fun, and that's what I'm passionate about, because I've been in the game for a while, and I'm like... And what I have done, people complain about New York or LA or dating, and I'm like, I have fun dating. I really, really enjoy it.
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Chapter 5: What are the top red flags in dating?
But I think you're saying such a big, I think of like Carrie Bradshaw when it was her birthday. She's like, I feel so alone. And I'm like, yeah, if you're single, you have to accept that you will be lonely. But is it worth sacrificing everything for the wrong person and feeling lonely all the time?
So it's either being lonely, occasional holidays or being lonely all the fucking time because you're with someone you don't actually like. But I think. What is really interesting about what you said is that a lot of times, especially in our early 20s, we're dating from a place of needing validation rather than from what we actually want. Yes.
So you're chasing the person or the goal, and you don't even know what you want. You're not even focused on if you like them because you're so focused if they even want you. Yes. So when you level up and you're like, hey, I am desirable. Someone would 100% want to date me. I was the biggest insecure baddie for all my life, and it's still something I work on. Yeah.
Once you start to date yourself and know what you deserve, even if you don't always believe it, but you have the discipline to act on it, you then can attract someone that sees your value, but you accept it. Because I also like the nice guy effect. You know when you date someone that's actually treating you nice and you're like, wait, what the fuck? Why is he weird?
Why is he weird? He's a psycho.
Yeah, he's a psycho. He's nice to me. He wants to take me to dinner. Yeah, yeah, yeah. But it's funny. You have to evolve yourself. You have to retrain your brain.
Yeah.
Toxicity is comfortable if it's all you've known. Exactly. So it's scary to take a shot on something that is new, even if it is what's good for you.
Oh, my God. This is like church.
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