She sets strangers up on the street—Tiff Baira is NYC’s ‘Official Cupid’

Tiff Baira wants you to admit that you crave being loved. She’s talking about you, with a roster, you, who’s so good at ghosting you could open your own funeral home, and you, who is “playing it by ear.” Tiff Baira wants you to know that it’s OK to want to be loved because even the worst of us all kinda, secretly do.

Baira would know better than most: in the past year, she’s helped couple up hundreds of seemingly undateable New Yorkers, earning her the title of “NYC’s Official Cupid.” You’ve most likely seen Baira on your TikTok ‘For You Page’ (she’s got over 229,000 followers) in her feathered cowboy hat, sitting strangers down on the street and asking rapid-fire questions to see if they’re a romantic match. Her series, Street Hearts NYC, is sometimes awkward, sometimes tender and always hilarious. It has led to innumerable IRL matches, and she tells me that people have walked straight out of interviews to go hookup. When Baira is in charge, she makes dating seem fun and easy, but most impressively, she’s managed to do it all in person. 

@streetheartsnyc “Ego” 😶‍🌫️ #subway #dating #nyc ♬ original sound - Street Hearts

Baira says there’s at least one thing about dating we can all agree on: We’re in the trenches, and you’d be hard-pressed to find single people who are happy with the current state of dating. Part of the malaise, at least in New York, is the feeling that we have infinite options—You’re telling me there’s all these hot people and I can’t sleep with all of them?—and nowhere is that false sense of abundance more evident than on the apps. 

Don’t get her wrong: Baira isn’t against dating apps, but she does think that they can give the illusion that we’re actively dating when really, most of the time we’re just having the same conversations in circles. “You can’t be stuck in app purgatory,” she tells Time Out New York after her cover shoot at the East Village’s Beauty Bar. “[The app] is like a plane, your vacation is not on the plane—you’re taking the plane to get to your vacation, which happens offline.”

Once you take the date offline, where you go first absolutely matters. “If you’re not compatible with restaurants I don’t know if you’re compatible in the bedroom,” she says. “If they send a reservation to a place you don’t like, tell them. If you’re gonna have a bad date you might as well have a good meal.” Among the places she recommends going for that first link: The Nines for a nice dinner; Tigre for an intimate speakeasy experience; Peak for good views of the city; Pastis for their martinis; Le Dive for wine; and you could never go wrong with a Lucien or Bemelmans moment.

If you’ve deleted the apps altogether and want to meet someone the old-fashioned way, there’s still plenty of good places to do that, too. Baira recommends SoHo Grand in Soho, 169 in the Lower East Side, Employees Only in Greenwich Village, Ray’s on the Lower East Side, The Wiggle Room in the East Village, and Cafe Balearica in Williamsburg. But Baira’s best tip for making a deep connection offline is even more simple: Just become a regular somewhere. 

Your bartender is your best matchmaker, she advises, something she knows a thing or two from having worked as a hostess at Soho House. “Finding love is luck and location. If you are a regular in some places you build relationships that help you get into relationships,” she says. “The bartender is also gonna know who all the single people are.” Plus, if you meet someone at your favorite New York bar, you already share something pretty fundamental in common.

Although Baira is an expert matchmaker now, all the knowledge she has comes at a cost. For the eight years that she’s lived in New York, she’s had every dating experience conceivable—crying drunk in the back of an Uber, seeing a date flirt with someone in front of her during the actual date, coming home to a cold, empty bed. For a long time, Baira didn’t even think she would find love. “When I was growing up, people that didn’t look a certain way were told they’re not eligible for love,” she says. “A lot of the dating advice that I was hearing was, if you want someone, you have to not be yourself.” But then she dated someone who treated her so poorly—or, as she calls it, the d*ck that broke the camel’s back (and not in a good way)—that she realized she needed to change her own understanding of what love looked like.

One thing that Baira is sure of? The age of “situationships” is dead. She says you can tell you’re in a situationship if you find yourself constantly confused about how much the other person cares about you or if they even want to be with you. The prevalence of situationships is a tragic byproduct of an app-fueled culture in which we see each other as disposable characters in a larger story that centers our own fantasies at the expense of others’ humanity. “We gotta stop viewing each other as just options, it’s almost like we’ve depersonalized dating so much to where we all feel disconnected,” she says. And when we’re treating each other like numbers and cut people out for minor infractions, it actually affects how we view ourselves, too. “It creates the idea that we ourselves gotta be perfect to be loved.”

But here’s the thing: Baira recognizes that part of the reason finding deeper connection in New York is so hard is also part of what makes New York great. There is no lack of love here: Love is in the bodega man who has your order memorized, love is in your best friend calling you out of the blue to go on a hot girl walk, love is in the person you make out with for 10 minutes at the club on a Thursday. You technically don’t need a love interest to experience intimacy in its infinite forms, which is part of what makes New York so enthralling.

At the same time, sometimes none of that feels like enough. Baira’s hope with Street Hearts is to show New Yorkers that dating doesn’t have to be so serious and that we can still love our bodega man while loving a significant other, too. She gets us in front of each other physically and helps us see that when you take a moment to notice, we’re all actually craving something deeper. She makes strangers stare into each other’s eyes and think about the possibility that at the other end of the table is not only the potential for more heartbreak but also, potentially, the type of connection that could transform our lives for the better. 

“After you meet the person that you really connect with, all those previous rejections and mismatches don’t matter anymore,” she says. But you can’t get there if you don’t believe that love is possible, or more specifically if you don’t believe it’s possible for you. “Ultimately, you have to start with the most important love story, and that is the love story you have with yourself.”