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Flirt School

I wasn’t born with the gift of banter. This summer, I tried to learn.

Photo-Illustration: The Cut; Photos: Getty
Photo-Illustration: The Cut; Photos: Getty

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Sometime in the past few years, I noticed I’d stopped making eye contact with strangers. I’d moved out of my parents’ house, where I lived during the early months of the pandemic, back to the city. But I rarely left my neighborhood or even my studio, never fully uncoiling into in-person life. There were no more charming barista encounters, no banter inside sweaty basement gyms, no conversations struck up in dimly lit wine bars or housewarming parties. “You’re so pretty,” the hostess at a hotel reception desk in the Bowery recently told me after I pressed her for the lobby Wi-Fi. Flustered, I volleyed the compliment back: Thankyousoareyou! Out of my mouth, the copycat words sounded unctuous and insincere, and she grimaced — there was no free Wi-Fi.

I wasn’t always this way. Though never a confident person, I once considered myself to be a confident flirt. There was no one I didn’t flirt with: waiters and weed dealers, authors I followed on Instagram, the crushes of friends on behalf of those friends. It was low-stakes fun, and we measured our successes by the number of horny DMs received. I don’t want any more of those, but I miss the poise and openness that came with being a decent flirt. Could I learn to become a better one?

When I ask a friend about this plan, she breaks it to me gently. “I don’t know that it can be learned,” she says. “The people I know who are good flirts have always been good flirts.” To be fair, this friend — let’s call her Alicia — has reason to be pessimistic. She takes cues from flirtier friends and practices at bars, but her interactions with men blow up anyway. “I try to look for an obvious in — What are you drinking? And the guy literally answered, I don’t want to talk to you. I was like, I don’t really want to talk to you either. I was practicing, but whatever.” Once, a man took Alicia up on her offer to buy him a drink, surprised to be asked. It seemed like a promising start, “but I would say it didn’t work, because this guy ended up buying six drinks on my card and giving them to other girls.” Alicia has learned to bypass traditional flirting tactics and go straight for negging, but that’s proved to be a mixed bag as well. She once talked to a man on an app for two years before ever meeting in person. “Our banter was straight cyberbullying,” she recalls. When the two finally met, Alicia kept up their cutting rapport. I said something really mean to him: You’re not as cute in person. It was meant as harmless banter, but it did not go over well. “He was like, Oh my God, you’re actually mean. I was like, We’ve been saying way meaner things to each other than that!” And then the date was over.

In other words, you’re either a born flirt or you’re not. Alicia points to a certain je ne sais quoi of her flirty friends. They’re skilled at starting conversations with random people who somehow become “very interested in what they have to say — I haven’t figured that out,” she says. Good flirting, in her estimation, means pivoting seamlessly away from the awkward moments and pressing on past the dead ends. It’s having everything you need to keep momentum even when the other person is giving you nothing. It’s comfort with rejection. “They’re just good at talking,” Alicia says. “So people like whatever they say.”

That night, I scrolled through cheese pulls on TikTok and considered Alicia’s assessment. I realized I’d probably never been a good flirt; rather, a two-bit sexter incapable of striking up meaningful conversation. I had to get better at flirting, or at the very least, better at talking, and I’m not the only one who’s desperate for a hack. On TikTok, relationship experts peddling their “juiciest flirting tips” recommend buying perfume that makes you smell “as close as humanly possible to a doughnut,” citing a study suggesting that the scent increases blood flow to the penis. (Or, if that’s too tame, wearing your own vaginal fluids as perfume, known as vabbing, which supposedly attracts partners by broadcasting your pheromones out to the greater public.) People are reaching for more old-fashioned methods too. Earlier this summer, Miriam Makalia Vance, a 28-year-old who works at an indie press, designed and printed her own cards to hand out to potential suitors: Hi, I think you’re cute, they read, with her Twitter handle and phone number at the bottom. If you think I’m cute too, get in touch. Vance doesn’t consider herself a bad flirt — she just wanted to do something different from the apps, avoid missed connections with cute subway strangers, and sidestep the general creepiness of approaching them. When we spoke, she hadn’t yet handed out any of her cards. She was thoroughly roasted after tweeting about them and worried that recipients would post screenshots online: “Oh my God,” Vance imagines her prospects saying, “This uggo gave me her card.”

After weeks of digging into the flirting regimens of hetero women, the process seemed more complicated than when I set out. I wondered if it was just the straights who, instead of chitchat, have resorted to dousing themselves with vaginal perfume. So I spoke with Lamont White, the Atlanta-based “Gay Dating Coach,” couples counselor, and matchmaker, who painted a similarly awkward picture after working with some 700 clients, mostly gay men and some straight women. “Guys come to me because they have no idea what they’re doing,” White tells me. Flirting is “the art of small talk,” he says, and being a good small-talker over text doesn’t necessarily translate. “Some people, especially younger folks, are amazing with text and online flirting, and when you get in person you’re quiet as a mouse,” says White, who advises struggling flirts to “practice being consistent” with both. If you need plain talking practice, he advises walking through a crowded park and making idle chat. “Do not wear sunglasses,” White warns. “Do not get on your cell phone and start texting.” 

Part of the flirting problem, according to West Village–based dating coach Amy Nobile, is that it’s a lot less sexy than it sounds. Through her $25,000, four-month-long coaching service, Love, Amy, Nobile helps singles with their apps and banter, rewriting their Hinge profiles and sometimes even responding to their matches. “We were taught flirting as a superficial feminine quality, whether it’s flipping our hair, showing skin, or a funny little laugh. Real flirting is none of that,” Nobile says. “It’s warmth and validation. Get in line at a CVS. Go up to the cashier and tell them, ‘Oh my God, I love your hair.’” So long as the compliment is genuine — and PG — it will land. “I see so much of going too far too fast physically because you want someone to like you,” Nobile says, “and part of my job is to slow it all down.”

She does this by taking clients on mock dates before their real ones, an opportunity for them to get out all their “squirming and stammering,” and for her to model what they should actually be doing. We meet over FaceTime. I’m working from home in my usual disheveled state; five minutes beforehand, I’m struck with sudden pre-exam nerves and decide to change out of sweatpants into a jumpsuit and add a smear of lipstick. In the first round, I do my best to be a good talker, asking questions and attempting to push past Nobile’s cold and aloof demeanor, which makes me feel like I’m on a job interview going south. (This is deliberate on her part — “That’s what 90 percent of first dates are,” she says.) Then she quickly moves into the second iteration of our date, where she takes on the jauntiness of a personal cheerleader. Strangely, I preferred the first-round iciness; the misanthropy felt realistic. This time she inflates me with compliments and looks for points of connection; she praises me for going to therapy and fake-asks me out again, but I’m even less at ease, flustered and bungling and lobbying her compliments right back to her as if it’s a transaction. Still, my shyness aside, she predicts it will be “relatively easy” for me: “You’re beautiful, make eye contact. It’s a little touch on the sleeve without being weird.”

The more experts I speak to, the more despondent I feel about this whole self-improvement endeavor. I have never been a confident person; the breeziness of the good flirts Alicia talks about feels exhausting to me. At a group falafel dinner, a friend shares an anecdote about a friend who’s been sexting with ChatGPT and considers herself more satisfied than ever. She has trained her bot to speak to her the way she wants to be spoken to. It sounds pretty nice.

One weekend in late July, I decide to put my education to the test. I need a people-person guide, but many of my friends don’t want to participate in a flirting adventure, citing long-term relationships. My high-school friend (and top-notch small-talker) suggests we attend a “potions class” at the Cauldron bar on Stone Street instead. She wanted to go there for some time to celebrate my belated birthday — why not toss in a flirting tutorial too? I take a tiny sliver of a Concord-grape edible beforehand to help be more friendly, and we file up a wooden staircase to take our seats behind two middle-aged couples in tiki-patterned shirts who appear to be on a double date. There’s no one to flirt with except them or the “potions master” dishing out instructions in a fake British accent. After one or two dry-ice drinks, we make our way to a wine-and-tapas spot next door. It’s dark and empty and also plagued with couples. But the bartenders, flirts themselves, make practicing easy. “You look like an Erica and a Sonia,” one informs us. “We are Erica and Sonia,” I reply. He nods. “I’m Dennis Rodman.” Maybe it really was that easy.

It wasn’t. Another friend of mine, a bona fide flirt and elementary-school teacher I’ll call Sadie, has a boyfriend, but she’s down to “help fight the good fight” the next night. (“He’s fine with it,” she says of the boyfriend. “It’s just flirting, it’s not like I’m fucking somebody.”) She chose the Spaniard, a horseshoe bar in the West Village, as our stomping grounds, because she’d been there a few times before and “brought a guy home back in the day,” which is enough evidence for her to conclude that the art is “alive and well” there. Before setting out, we meet up for pizza nearby. I wear the conformist uniform of beige linen pants and a white tank. Sadie has on a little black dress and a pair of earrings resembling two bags of carnival goldfish in plastic bags. “They’re conversation starters,” she explains to me over our food. As if on cue, a waitress stops at our high-top: “Oh my God, I love your earrings.”

The expert advice does nothing for Sadie, who has her own tenets for flirting: Vulnerability and warmth is well and good, but doing it for pure fun is perfectly fine, too, she tells me. “I ask a question to loosen people up,” she says. “Like, would you rather get with Hillary Clinton or Queen Elizabeth?” Her metric for success is refreshingly straightforward. “We’re only paying for our first drinks,” she says. “If we pay for our second, we’ve failed.”

When we arrive, the Spaniard is already packed, and we’re immediately cornered by two inebriated brothers conveniently positioned at the entryway. They’re from Dublin, and one brother jokes to me that he performs as Niall Horan in a One Direction tribute band. We keep up the schtick, but when I ask him where Harry is, he grows serious: “I don’t actually do a tribute band,” he says. “I work in advertising.” As the brothers order more drinks, Sadie whisks me away to search for our next recruits.

She surveys the room, spotting three men orbiting the same disinterested girl like a planetary system of muscle shirts. I remember some of Nobile’s advice from our mock date: It’s not always about being asked out, she explained, it’s about engagement. But even with all that coaching about small talk and mock dates, I can’t walk up to them. So Sadie does, striking up conversation with two out of the three planets, wealthy Jersey boys who are stressing out about whether the Champagne gun they bought for one of their annual summer parties will actually work. “I work at McKinsey, if you’ve heard of it,” the party-thrower says. He quickly grows enamored with Sadie, buying us both tequila seltzers at her request (“He is a cheapskate,” the other Jersey boy teases, so this is a big deal) and reinforcing his interest in her by steadily negging me. “Your bag says New York,” he laughs at my magazine tote. “Do you forget where you are?”

Later, I approach two men in hats — one in a pilot hat; the other in a cargo-printed bucket hat — and ask why they’re wearing them. One starts showing us iPhone photos of himself in a romper; the other considers me: “If you weren’t so short, you could model.” Thankfully, we lose them, too, ebbing and flowing through the crowd. The quickness with which we shuffle through prospects who turn us off makes the room feel more like a sea of sweaty in-person dating-app profiles than a congregation of people; the mind-set of swiping still applies here. Flanked on all sides by the backs of tall men, Sadie makes a proposition: Tap one man’s shoulder and ask him if he believes in aliens, especially after the congressional hearing.

Before I tap, two men turn of their own accord. “I’m sorry,” Sadie apologizes to me quietly. “The guys used to be cute here.” The four of us discuss aliens, agreeing they exist; one of the men takes it a step further, polling us as to whether or not we’d fuck aliens given the chance. The other looks at me expectantly. I sip my seltzer, trying to think of something kind or complimentary to say to him, or even, per Alicia’s advice, something unkind or teasing. I can think of nothing except how smart aliens are to avoid us — how lucky they are that they’ll never have to flirt with us, knock on wood. His fleeting interest is already gone, and I’m relieved when Sadie befriends a woman flanked by men and pulls her into our conversation; she’s happy for the out. What does it matter if I can’t flirt, as long as I’m friends with someone who can? The three of us tag along with a larger group and file out into a basement bar. Thanks to Sadie, we have not failed: Someone thrusts more tequila seltzers into our hands. I retreat to the bathroom to catch a breath; Sadie joins me and helps me recover the contact lens that’s recessed behind my eyelid. We call it a night there, after so much small talk with so many strange men. So much of it has gone nowhere, but at least Sadie has made a friend, and a platonic connection is more than a hopeless flirt can hope for these days. “That girl I was talking to?” Sadie shakes her head. “She’s a flat-earther.”

Can You Teach a Girl to Flirt?