Would you pay $100k to get a boyfriend?
The woman setting up New York's wealthiest women with 55-year-old angel investors, "sensitive alphas,” and eligible mensches.
Good afternoon everyone. I was reading through some New Year’s Eve reporting archives this morning to get in the spirit. In a 1995 New York Times story about people making advance reservations for New Year’s Eve 2000, a spokesperson for the London Savoy said that the swanky hotel had been fully booked for its new millennium party since 1990. New York’s Rainbow Room also stopped taking reservations (with a $500 deposit, which would be about $1000 today) for Y2K five years before it arrived.
Today’s letter includes: The young people using dating apps as LinkedIn, the Pornstar Martini makes a comeback, Matt Rodbard’s food media predictions for 2026, and Arnold Schwarzenegger’s crash diet for the mind.
We also have Cami Fateh’s latest party reporting column. This week, Cami wrote about a recent night out with Bonnie Winston, a matchmaker for millionaires — not to be confused with Patti Stanger of The Millionaire Matchmaker, with whom Bonnie works closely — who pulled the curtain back on the state of dating for the wealthiest, most eligible single women in New York City. Women turn to Bonnie when they’ve been bamboozled by dating app frauds (one client claimed to have lost $2mm to a man she met on Hinge), or need coaching on how to flirt because according to Bonnie, they’re “alphas at work.” The mundane horror of being a woman is endless.
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Political Parties is a nightlife column by Cami Fateh. It offers readers a glimpse into the unspoken politics of party culture, in rooms that they didn’t even know existed.
During the dark, slow days between late December and New Year’s Eve, a damp quiet falls upon New York City. Friends have skipped town, posting photos from warm family cabins upstate or ski houses to which you weren’t invited. The bars are empty, party dresses have been deposited at dry cleaners, the snow falls and melts, and those who are still in the city, bundled on another late subway ride, really only want one thing: someone to love.
I spent one of those evenings during holiday limbo with a person whose life’s work is helping New Yorkers meet their soulmate: Bonnie Winston, the self-proclaimed “celebrity matchmaker” who will find you love – for $100,000. I wanted to ask her whether app dating has become so horrible that people need to pay six figures to thrive in cuffing season, and what her secret sauce is to matching up two strangers – she told me, over email, that her success rate is “around 90%.”
“Oh my god, do you have a boyfriend?” was the first thing Bonnie Winston said to me, after introducing herself with a big hug, when we met for dinner last week. I smiled and told her I did. “DANGIT! I wanted to fix you up… gratis” she said, jokingly pounding her fist on the bar.
Bonnie is a bouncy woman in her 60s sporting a black mini dress with all-over-sequins, pink lipstick, and blonde beach waves with a fresh money piece. She flagged over a bartender (“Hi gorgeous,” she purred) who greeted her by name and told me “you’re in good hands with Bonnie,” as if we were sitting at the local watering hole in a Netflix Christmas movie instead of Flyfish Club, a downtown members-only cryptocurrency restaurant with an omakase counter.
She recommended the hamachi crudo (“DELICIOUS”), saying that one of the club’s cofounders was formerly the head chef at Lure (“I LOVE Lure”). When the waiter arrived with matching lychee martinis and raw fish, Bonnie gave him a hug and a kiss on the cheek: “Hi Tony, doll.”
I asked Bonnie if she came here often, since she seemed to know everyone. She shrugged, and said “Not really. I can scout at a laundromat. I can scout just about anywhere you put me.”
It took me a second to realize that “scouting” meant finding potential matches for her clients (who are almost all women) and contacts for her “Date-A-Base,” the vast network of eligible bachelors that she scans whenever she signs on a new client. Sometimes, she scouts via her “ins” at university alumni associations – she says that Harvard Business School and Wharton used to have the hottest guys, but now Duke is in first place, followed by Michigan. She’s also placed ads in Harvard Magazine since the late 2000s, and she’ll occasionally put out classifieds for her clients in the New York Review of Books if they identify as “sapiosexual.”
Other times, she’ll hit up her own personal network, like the time she cold-called a friend from sleepaway camp, who she hadn’t seen since in over 40 years, for a client. (“Remember when I was Dorothy and you were the lion in The Wizard of Oz? Don’t hang up, don’t hang up!” she said, re-enacting their phone call). Most of the time, however, she’s scouting as she goes about her business in the city.
Bonnie looked over at the men standing to the left of us at the bar and wrinkled her nose. “Not cute,” she said. Then she pointed to the right, where a group of men in suits were settling in. “Now, they’re cute. I’m going to get their info,” she said, grinning at none of them in particular, and they locked eyes with us and smiled back.
“People have a driver, they have a trainer, they have a chef, and they have a matchmaker. It’s outsourcing.”
Matchmaking has long been at the heart of stories like Hello, Dolly!, Fiddler on the Roof, Emma, and its ‘90s counterpart, Clueless. Bonnie said that “a friend once told me that going out with me is like going out with Dolly Levi [the fictional matchmaker in Hello, Dolly!] to Harmonia Gardens!” But this year, the practice experienced a cultural resurgence with Materialists, and multiple very similar stories that urged people to resurrect the habit of matchmaking their friends, citing dating app burnout. A friend of mine from college launched a mutuals-only dating app called Cerca, which is supposed to replicate the experience of a setup.
Tech founders also stepped in to try to solve heartache with AI. Hinge’s CEO left the company to start an AI dating app. Nandini Mullaji (who writes Guru Nandini Says on Substack) launched an AI dating app. Meanwhile, dating apps doubled down on slop, and people started using AI to write messages, help craft profiles, and play algorithmic matchmaker. Disappointment with modern dating has only caused Bonnie’s waitlist to swell, she says, and she’s been featured in The New York Post as “Real Life Materialists” and helped organize an IRL “YentaCon” for Jewish matchmakers.
Before Bonnie became a full-time matchmaker in 2013, she had a modeling agency called Elite Petite (“We used to call it heaven under 5 ‘7,” she said). By night, she set her friends up for fun: she matched up her best friend at a bar when they were 16, and they’re married to this day.