“I would make all of her dreams come true and she doesn’t even give a fuck about me,” Mikey says. “Not even a little bit. Not even a slight desire. None. Nothing.” It’s nearly 1:30 a.m. and I’ve been listening to this spiel all night. We’re sitting on the roof at Casa Cipriani, the city spread out and shimmering all around us. Mikey’s talking about beautiful, blonde Stella, who’s currently traipsing away.
“She honestly seems slightly uncomfortable,” I say.
“She’s honestly a fucking smokeshow,” Mikey says, as if this isn’t obvious.
Perhaps as a form of consolation, Mikey turns to Nina, Stella’s friend, and asks — of all things — about her new job working in the pediatric surgery wing at Cornell. I’m grateful for the minor reprieve from Mikey’s pursuit of Stella in exchange for normal conversation, but it doesn’t last long. Mikey can’t help but put his foot in his mouth. He interjects mid-conversation: “Your friend’s tights have me hard as a rock.”
Let’s rewind. Mikey, George, Mario and Eddy (some of these are aliases, some not; I’ve been forbidden from printing any last names) are having what they call a “wholesome night” for four guys who normally drink until sunrise. I’ve known George and Mikey for years through bartending, and — like most straight men — their two objectives for a night out have never strayed from getting hammered and taking a woman home. Was the latter always accomplished? Maybe, maybe not. Did I want to find out? Obviously. I’m extremely nosy.
Given the alarming stats concerning young men and their inability to meet women IRL (some 45% of men aged 18 to 25 have never asked out a woman in person, apparently), I wanted to meet men who are actually bucking this trend. To study them, as it were, in their natural habitat. To be the David Attenborough of horny bros unafraid to roll the dice by chatting up women at bars and clubs across New York City. It is, after all, a subject that interests me.
I told Mikey as much and, a week later, he invited me along for their next Saturday night outing.
“The main issue is social media and dating apps. People are flooded with options, and then scared in real life, or scared of ‘cancel culture,’” Mikey says. He doesn’t use social media or dating apps, which he claims is a “massive green flag,” and a way to “force real-life interaction.” Hmmm, maybe. Although to others this might be a massive red flag, as in: is there something so sketchy about your past that you’ve abandoned social media in fear of being, dare I say, doxxed?
I decided to take Mikey’s word for it and join him and his friends.
Mikey, 27
From: New York, NY
Occupation: Owns a metal fabrication company
Seeking: A wife
Actually seeking: Attention
George, 26
From: New York, NY
Occupation: Creating a party pop-up label, or being the party. Unclear.
Seeking: A few drinks with the gang
Actually seeking: To be in bed with his girlfriend, Yas, before midnight
Mario, 26
From: Italy, currently living in Zurich
Occupation: Investment associate at a PE firm
Seeking: A fun night out with the boys before he returns to Zurich
Actually seeking: Margo, his vacation tryst
Eddy, 26
From: Italy
Occupation: Finance for Loro Piana
Seeking: To not be cucked by his lover’s ex
Actually seeking: Sleep. Jet lag comes for us all.
7:00 p.m. George instructs me to skip The Yacht Club, where the evening has commenced, and head to LoHi in Williamsburg for the Toy Tonics set. I book it there in an Uber, google “Toy Tonics” — a Berlin-based house music label — so that I can pretend I know what it is when I see them. I don’t love house music, but everyone in this city seems to, so maybe I’m the one lacking taste. Upon arrival, I immediately plop stoopside while I wait for the boys. The block is in that quiet, warehouse-lined back area of Williamsburg, and the only people on the street are bustling in and out of LoHi’s entrance. George drives by in his Audi (which I clock as vaguely Q5-shaped). He parks on the next street and we all convene, hugging and kissing cheeks. Along with George, Mikey and Yas (George’s girlfriend), there’s Eddy and Rafaela, and I’m reintroduced to Mario (who I’ve met once before). I feel so…American among the boys’ Italian (and Rafaela’s Brazilian) accents.
7:12 p.m. We immediately lose the Italians. We won’t see them again until we leave for dinner. Mikey surveys the rooftop, checking out the variable crowd consisting of medium-height men in soccer jerseys and lanky women sporting their favorite low-rise jorts. He turns to me, arms folded and brow furrowed. “Status report: Not a whole lot of lookers here.” I laugh, and I judge a little bit. You know that saying “We listen but we don’t judge?” Does not apply to me. I can’t help but think about how Mikey and George are the topic of frequent discussions among the staff at my bar because they’re always bringing the hottest 20-somethings we’ve seen in for drinks, so I know what a “looker” is to them. Real hot. Model hot. An NYC “10.”
We trail George toward the DJ booth. George daps up the DJ, Mathias Modica, aka KAPOTE, co-owner of the Toy Tonics label. George later tells me about running his own “house party pop-up label” (whatever that means), so his connections to DJs appear to be unlimited.
7:55 p.m. Mikey tells me he’s “always looking” for his wife and laughs, but it’s a forced unhinge of the jaw, some electro-shocked bark of a laugh. I know him — despite all the bluster, there is a girl who he cares for in a real way. She has no idea how he feels about her. He won’t talk about her much. Some nights he sits at my bar alone, wired earbuds glued in. His eyes rest empty on some spot behind me. I imagine, all those times, he was thinking about her.
Mikey is a born and raised New Yorker, now estranged from his friends Monday through Friday on the lonely coast of suburban Connecticut. The reason? Golden shackles — i.e., “owning a successful metal fabrication company” — which he’s been running for the last five years. So, during his city weekends, dude lets loose.
The music is ear-splitting. I shout-ask into Mikey’s ear if dating is easy for him. Instead of answering me directly, he keeps emphasizing how there’s “not a lot of ‘talent’ here,” while hitting on exactly zero women. Mikey’s hot take: “Dating in NYC is incestuous.” As proof, he does some senseless math that doesn’t add up. Still, if I consider Mikey and the crowds he runs in, then I can wrap my mind around his gripe: too much overlap.
8:33 p.m. I abandon my post and tragedy strikes: Mikey is “cucked,” as he calls it. Read: a more aggressive form of cock-blocking, this time by a guy scooping some German girls out of his grasp.
“It’s a cucking economy out here,” Mikey says. “Everyone’s just trying to find someone to fill the chair, y’know?”
Mikey is double-fisting Margaritas and dancing next to whatever women bump up against us. I can’t look away, nor would I dare — I abandoned my post for 30 minutes and missed the cuck economy in action.
9:10 p.m. Next location. We take two Ubers.
9:35 p.m. We head to Yopporai, an izakaya on the Lower East Side. Mikey orders for everyone. Rafaela orders a bottle of Suigei sake. Mikey orders too much agedashi tofu.
We settle in, shoeless and cross-legged, as the sake shots start rolling. Conversation ranges from a friend’s arrest on Paros for flashing his bare ass at a club (they showed me unsolicited video evidence — just kidding, I totally wanted to see it) and pointing out tonight’s evident lack of blacking out and getting arrested. They keep mentioning “Tommy,” a so-called psychopath who, for better or worse, isn’t joining us tonight.
Eddy confesses that he feels he’s getting cucked by his situationship’s ex. Cucking seems to be a constant point of contention for this group, or maybe men in general — it’s a specter that looms over the entire night’s proceedings. You’re a big dog or you’re being cucked. The center does not exist, nor will it hold. Eat or be eaten.
11:07 p.m. The group fractures. Eddy, George, Yas and Rafaela all choose sleep over further partying. This night might be a wash, I think. But when I see Mario doing a costume change in the middle of Clinton Street from a regular tee to a collared shirt so he can abide by the Casa Cipriani dress code, I know the night is still young and worth observing. Ye of little faith.
11:22 p.m. We arrive at Casa Cipriani, aka the waterfront private membership club in FiDi, and Mikey, who is a member, is immediately beefing with the doorman over his dress-code violation. Apparently, men cannot wear short sleeves. Newsflash for Mikey, who is wearing a collared short-sleeve shirt. The doorman insists that Mikey must wear a Cipriani-branded blazer. Mikey is beside himself, but obliges.
While Mikey seems to know the entire staff and is on a dap-them-up-and-hug basis with at least 10 of them, he is not immunized from forced blazer-wearing.
Waltzing through the joint, I take note of Casa’s upper interior. Velvet furniture. Warm, ambient lighting (I can barely see a goddamn thing). Waitstaff adorned in white coats and black bowties whisking past mahogany walls so lacquered you could ice skate on them. Also noted: a lack of bodies inside. The real party, apparently, is on the roof deck.
11:48 p.m. I taunt Mikey into action by doing a voice-to-text note: “It’s 11:48 p.m. and Mikey has hit on zero women.”
“No, I hit on some women before I got cucked, which did discourage me,” Mikey says.
Tsk, tsk. Excuses, excuses. Mikey sighs, burdened by the weight of “the game.” He takes my taunting bait and turns to a sexy, slightly older (than us) lady, who, after only a few moments of close-talking, grabs his ass and stares at his mouth when he talks. I assume they’ve already slept together. Meanwhile, Mario, the Italian, just got scammed by a Casa Cipriani waiter and paid him $50 for Marlboro Lights. I let Mario know cigarettes go for $20 in New York. He says, in his accent, “Is okeeey, is okeeeey.”
11:59 p.m. Mikey returns five minutes later with his post-game: he’s taken this woman to dinner twice, knows she won’t “give it up,” and thinks she’s playing hard to get because “she’s full of shit” — or, as I translate it, she wants me but won’t sleep with me as part of a game. Who’s winning? He says he’ll try a couple more times, then asks whether her gallery invitation was genuine interest or just promotion.
12:31 a.m. After Mario and Mikey secure a table, they leave and quickly return with three women that Mario had called and invited during the Uber over. I am delighted by their beauty. Italian and gorgeous. Bravo, Mario. I come to learn their names eventually. We’ll call them Nina, Stella, and Margo.
I switch seats with Mikey so he can be closer to the girls, and so I can observe them. Margo, seated closest to Mikey, offers up a coquetteish, girly look. In the middle, Stella exudes sultry in an all-black ensemble featuring black lace tights, while Nina, chatting with Mario, embodies classic Italian elegance in a white maxidress. Here, finally, are the “talent” or “lookers” Mikey so fervently sought hours earlier.
How to Hit on a Woman at a Bar
Our resident female bartender dispenses crucial tips that just might improve your real-life love life1:00 a.m. A tablewide debate sparks up. I sit back and ash my cigarette into a melted drink, trying not to laugh. The question is about what women require before agreeing to a date with a near-stranger, but Mikey takes the reins — his asking Stella out is the talking point that ignited this after all. He uses what must be his secret weapon: me (somehow). He claims that he’s not “just some random guy,” and lets the girls in on his secret: “Dani is writing about me right now.” The girls’ faces are lined with disbelief. Mikey presses on undaunted. He says that I — aka me, Dani — am covering the most interesting men — aka Mikey and his friends — in New York. The girls laugh, eyebrows still raised in my direction. I meet them with a shrug. Who am I to get in his way?
1:20 a.m. The rooftop begins emptying out. Mikey has been steadily working Stella toward a dinner date. Mario has been talking to Nina the whole time, but I suspect by body language that Nina is not the object of his desires. Stella is being regaled with tales of Mikey’s famously good dates (he says he’s never had a bad date, which isn’t quite the same as always having good dates, but I let him cook). Stella inquires about what a date with him looks like, which sounds like a goad for him to say something stupid. Mikey explains: dinner, then it’s “anyone’s game,” depending on who has control. I ask, how do you know who has control? “Whoever’s hotter,” Mikey says with an easy smile. There has yet to be a point in the night where he seems serious about anything at all, which seems evident to Stella too. With each goofy grand gesture, Stella smiles at Mikey. When I ask Stella how Mikey is faring, she tells me she loves a little lovebombing, and wouldn’t mind being “gaslit” into a date.
1:25 a.m. I finally ask Mario which girl he’s into. He confesses to seeing Margo, of the Italian Sexy Girl Group, for a few weeks — they met on vacation in Porto Cervo, Sardinia. Honestly, they’re cute together. Mario also strikes me as a sweeter counterpart to Mikey’s absurdity. With this confession, Mario and Margo cuddle up on the couch, chatting. I sit next to them, Stella next to me. Across from us are Nina and Mikey. Perfect.
1:54 a.m. Mikey continues to lovebomb Stella, inviting her to his upcoming family dinner at his parents’ place on the Upper East Side. She calls him crazy. He attempts a compromise in the form of an omakase date, and she says: “You talk too much, basta!”
From her pouted lips to God’s ears. Evidently, God is not listening, because Mikey continues talking.
2:07 a.m. While Mikey covers ground with Stella, Margo, tearing herself from her canoodling with Mario, interrupts as she hears Mikey call Stella “sweetheart” for the fourth time. “Mikey, what’s her name?” She’s pointing at Stella. I know Mikey has no clue.
“Starts with an S,” he says, which is actually more than I thought he knew. Stella no longer feigns annoyance. She is genuinely vexed, huffing and crossing her arms.
2:11 a.m. Official time of death for Mikey and Stella’s relationship.
2:14 a.m. Nina tells Mikey Stella’s name, so he is emboldened to revive their love. So many men would have given up so many rejections ago. Not Mikey. He mirrors her body language overtly, crossing his legs and flipping his imaginary blonde hair, which earns him a melodic laugh from Stella. He talks to her like he’s making a deal: Come on, dinner? Tomorrow night? Omakase? Lunch? Brunch?! The desperation in his voice is exaggerated, blown out of proportion — but it’s also…working?
He swears on his mother’s life about giving her the best dinner of her life. Stella says she doesn’t like people who swear. I resist the urge to bite my nails or light another cigarette. Mario pleads with her (“Come on, it’ll be so fun, you’ll have such a great time,” he says), breathing a faint whisper of life back into their corpse of a relationship.
“You’re such a good wingman,” Stella says. Mario continues selling Stella, compromising on Mikey’s behalf and pushing the date further and further away from “tomorrow.” Mikey chides him for pushing the date. I’m watching this like a tennis match. Mikey puts his hand out to Stella, inviting a shake.
“Come on. Dinner tomorrow?” There is a tone of finality lacing his voice that hasn’t made an appearance all night. Stella clearly recognizes it. She puts her hand in his and they shake on it.
2:18 a.m. The staff finally kicks us out after numerous efforts.
2:25 a.m. While everyone outside Casa Cipriani calls Ubers and Lyfts, Mikey continues pursuing Stella, asking for her number and referencing future plans. She gives him her number at last. Mario and Margo leave separately but at the same time, Nina alone, and before I can see whether Mikey and Stella leave together, my own chariot arrives.
I came to find out later in the week that Mikey did, in fact, take Stella out to dinner the following Thursday night when he texted me: “Let the record show that my streak of no bad dinner dates lives on.” He did not take her to omakase, but to Farra, a wine bar in Tribeca. She also joined them at a party George threw a few nights later. Not a single part of me was surprised to hear this. Does Mikey come off as arrogant, especially when laying out the details of his antics through a detailed, time-stamped report? Absolutely. But I would be remiss not to commend him for his stamina and persistence. If there’s a line to pestering a woman for a date, Mikey never truly crossed it — Stella was smirking the whole time (except when he didn’t know her name), and clearly, they were playing this game together.
I don’t think he’d have the same luck on an app.
Do you think your group of friends could outdo these guys’ night out? Email me and we’ll find out.
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