Photo-Illustration: by The Cut; Photo: RAGAN HENDERSON
After an hour with Tiff Baira, host of TikTok talk show Street Hearts, my faith in dating has been restored. The 29-year-old content creator is bubbly and bright and has been making videos about dating in the city since the pandemic. She calls herself New York’s Cupid, while offering up advice. “I was a hostess at Soho House when I went viral for the first time, and I got a lot of my inspiration by seeing a lot of shitty dates,” she tells me. “I was on the other side looking in and being like, Dating cannot be this hard.” Despite her optimistic nature, Baira is not naïve (“sometimes dating can be horrible”), but she firmly believes that going on dates should be fun. And who doesn’t want to have fun?
How much does your own love life influence your content?
I struggled a lot with my body and dating from a place of insecurity, especially when I was younger. I would always think that I was lucky to date people and then I was dating the wrong people for validation. So I really had to learn how to pull myself by the bootstraps and get out of the mud of dating and be like, It’s not normal for me to chase after a man like I’m a fucking Olympian just because that’s all I’ve ever done. When I’m giving advice on how to be confident in dating, it’s because I know what it’s like to feel like you’re not deserving of love. I know what it’s like to feel like you’re not pretty enough or good enough. As I’ve continued to make my content, yes, I hope it’s helped a lot of people to date more confidently, but it’s also helped me understand that I deserve more, too. Sometimes when I’m going on a date, I’ll watch one of my videos and be like, “Listen to that bitch.”
What was the craziest thing you saw when you were a hostess at Soho House?
You will see people go on dates by appointment. So they have a 5 p.m. date, a 7 p.m. date, and a 9 p.m. date, and by the end, they would give me an extra tip, being like, “Act like I just walked in.” And I’d be like, “I got you, bro. No one’s gonna know.” It’s the Charlotte York of it all, where she’s penciling in all of her dates to see which one’s the best. If you haven’t dated in a while, I recommend breakfast, lunch, and dinner, babe. If you don’t enjoy the men, make sure you enjoy the meal.
How can you tell when sparks are flying?
You can instantly tell when the sparks are flying because the eye contact is locked in. I think it’s so important when you’re talking to someone to hear what they’re saying, but it’s all body language. If you’re sitting there on a date like this [crosses arms], you’re not interested. I’m so over-chalant. Cut the nonchalant shit out, okay? I can tell that people like each other when they’re leaning in, when they’re laughing.
What’s your No. 1 rule for flirting?
Flirting is just being hot and yapping. I call it the volleyball strategy, so it’s like if they say, “I love pizza,” you’re like, “Amazing — pineapple or bell peppers?” You could be talking about the stupidest shit, but it’s not what you say; it’s your interest and excitement to be there. Truly, the best advice is just to ask questions. Be curious. Act like you’re on a date with someone that you’ve been a fan of for a while. And can we bring back decorum? Put the phone away. I went on a date, and a guy had an AirPod in.
That’s crazy. Did you ask what he was listening to?
No, I honestly just left. Restaurants have a 15-minute grace period, and so should you on a date. I used to feel like, Oh, I have to be polite. I can’t hurt their feelings. Don’t go out of your way to hurt someone’s feelings; we’re all being vulnerable. We should actually be a lot kinder to each other when we’re on dates. Even if you know it’s not gonna work out and you wanna go, you don’t have to be like, Let me jump out of the bathroom window, but just say something like, “Oh my God, I’m so sorry. I just got a Slack,” and I’m tired of hearing you yap, I gotta go.
What type of summer is it for girls?
We’re having a romantic-girl summer, but we’re outside.
Where should we be going?
If you wanna shake ass and go to the club, the main place where I hear that people are going is Casablanca; they play ’80s music. I know Jean’s has hot guys. Nowadays is like a day party. I love dancing in the day. Wiggle Room is for my young girlies. If you want to meet like a guy that definitely has a Roth IRA and won’t shut the fuck up about his Rolex, I’d go to Little Sister. If you’re on the younger side, I think Kind Regards is so fun.
Where I genuinely love to go myself is People’s: There’s really nice guys there, and it’s such a vibe. I also love being outside with my little book, a little journal. I love Bar Valentina, it’s such a nice place on the Lower East Side to just sit and hang out. Bring yourself on a dinner date to Lucien. I think going out to dinner is the best way to go out and meet people. I love the Hotel Chelsea, and you can just sit at that bar. Old Mates is in Fidi and the perfect place to find a guy. If you love a Bushwick mullet king, you got to go to Bossa Nova or Mood Ring. I think Elsewhere is really cool because they’re like, “I’m in the band.” And I’m like, “I’ll be your groupie, daddy.”
When you’re there, do you have rules? Will you start a conversation with a guy, or do you feel like the guy needs to start a conversation with the girl?
I don’t believe in necessary gender roles when it comes to dating. Dating rules are not one size fits all. Instead of listening to these antiquated laws and rules about what men and women should be doing, number one, you should ask yourself, “What do I want?” I do like it when a guy pays for my dinner. But if I actually went on a date with a guy and I didn’t like him, it can feel really empowering to be like, “Hey, actually I got this. Please never talk to me again.”
Have you ever been into someone on your show and then asked them out later?
You don’t mix work and pleasure, no. I think there are enough single people out there that I don’t need to use my show to date.
Your show has also changed now to include famous people and movie promos, which I think is really fun. What’s your No. 1 rule when it comes to meeting other famous people?
With my show, with everything that we do, I want everyone to get celeb treatment. But at the same time, I’m going to ask celebs the same questions that I would ask anyone else. What’s really cool is that when we do have these celebrities, we also have singles in New York who are on the show, dating at the same time. You get to see a whole new side of these celebrities. We actually put Sombr on a date with a random single girl in New York.
How did that go?
It was great. But that’s what the power of the show is like: You could literally go on a date with your favorite celebrity.
How do people get on your show again?
We have an application. We do this whole process of matchmaking. We don’t want to just set you up with someone random. We want you to let us know what your preferences are, what you’re looking for, who your celebrity crush is, all this stuff, and then we get to cooking.
Did the girl who matched with Sombr have him as her celebrity crush?
No, I don’t even think she knew who he was.
You call yourself Cupid. What’s your No. 1 rule for being New York City’s Cupid?
You have to shoot your shot. Your biggest regret should be not finding out.
How do you cancel plans?
I love pulling out an “I’m just so bogged down with work.” But we have to stop canceling so much. I feel like showing up for your friends has been lost. If you really don’t want to go on a date, you’re overwhelmed, fine. But show up for your friends. And even for a date, even for anyone, do not cancel two hours before.
How do you deal with ghosting?
If someone’s canceling on you for a date and doesn’t actively give you a new date and time, they’re just ghosting you. I’ve dealt with a lot of Casper-the-fuck-boy ghosts, and sometimes I prefer a ghost. Let me live in delusion. I don’t need a whole MLA-formatted paragraph of you telling me why you don’t like me, but let’s not ghost each other if we don’t have to. But if you don’t like someone and it’s just because there’s no compatibility, a simple, “Hey, that was fun. I don’t think we’re a match,” is all you have to send.
Do you feel that dating sucks right now?
It’s really important that we move away from the dating-sucks rhetoric or that if they don’t match every checkbox in my hypothetical list, then I’ll never even give them a chance. We’re all overly protective of ourselves and calling it peace, but sometimes you have to unprotect your peace for the right things in order to actually put yourself out there and date. Dating is not something that you can curate. There’s a beautiful mysticism and magic about when you meet that person, and sometimes you don’t know why you like them so much. I hope that we move forward — even if it’s just hookup culture or if it is looking for the one. We’re not AI. We are not an algorithm in which you can build a baddie. You can’t build a man, you can’t build a baddie.
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