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Ask any fed-up single what the NYC dating scene is like today, and you’ll most likely get the same response — it’s chaotic, messy and the apps are a drag.
No one wants to commit. Hookup culture is at full speed. And ghosting is at an all-time high.
As a result, desperate Big Apple singles are seeking alternatives in their city-wide search for love and placing their trust — and considerable funds — into the hands of professional matchmakers.
Elliot, a Big Apple-based former attorney turned house-flipper, made a promise to himself that if he were still single by his 40th birthday, he would succumb to handing his love life over to a professional matchmaker.
After interviewing with three different high-end matchmaking services in late 2020 and early 2021, the now 45-year-old signed up to be a part of the free matchmaking database of London-founded agency Maclynn (formerly the Vida Consultancy) to be placed in the agency’s complimentary pool of potential daters, and met with Carly Spindel, half of NYC’s Janis Spindel Serious Matchmaking mother-daughter team.
Though Elliot, who preferred to go by his first name, was initially “more than willing” to pay the hefty $25,000 fee for a starting contract at the time, he quickly realized the service was “everything I didn’t want.”
“She [Carly] was happy to tell me she had a Rolodex of girls with all their pictures and that before she sets them up on a date, if she meets with them in winter, she has them take their jacket off and do a little twirl,” the Upper East Sider told The Post. “I was like, okay, if you can’t get enough from a basic picture and that’s your sales pitch — really not much else — that’s not what I was looking for.”
Elliot instead signed on with Three Day Rule — an LA-founded luxe service where singles get paired with a personal matchmaker and coach to match them with a potential suitor based on goals, values and lifestyles, costing around $20,000 for VIP membership, with a recently offered $1 million dating package for ultra-VIP clientele.
Though he declined to disclose the exact details of his contract (including how many dates he went on and how much he actually spent), he shared that his “insightful” matchmaker, Kristen Stewart, gave him a wealth of sound advice, “cheerleading” support and dating feedback, eventually matching him with his now-wife and mother of his child in 2023.
“We sent Kristen an invite to our wedding,” Elliot told The Post. “She even came to our apartment shortly after we got married…It wasn’t just, ‘Okay, I found you a girl and now we’re done.’ She was phenomenal the whole way through.”
Aside from weaning through NYC’s sad pool of singles, what exactly does a costly matchmaker contract buy someone?
Bonnie Winston, one of NYC’s most sought-after professional cupids, whose six and twelve-month contracts start at $60,000 and can balloon up to $200,000, keeps clergy-type hours to appease her tight Rolodex of affluent clients, who include everyone from millionaires to A-list celebrities.
Between deploying custom hair and makeup teams to clients’ homes before dates, virtually vetting potential suitors, making them “stand up over Zoom,” and even connecting some singles with trained psychotherapists, the 25-year industry veteran is proud to serve at love’s constant beck and call.
“You can call me at midnight,” Winston told The Post. “Say you’re on a date and you’re in the bathroom, going, ‘Should I go home with him?’ I’m going to tell you ‘yes’ or ‘no’… A lot of things that happen when you’re a matchmaker don’t take place from nine to five. They happen when the date’s happening.”
Winston, who describes her main client base as “women who have lost love through death, divorce, or disappointment,” generally prefers to work with this group because she finds that higher-earning women are more often searching for a meaningful connection, rather than a match-after-match dating service.
Whereas male clients are continuously on the hunt for their perfect match, sometimes for the wrong reasons.
“I called [a male client] and asked how it went,” Winston explained. “He said, ‘… she was beautiful inside and out, just my type…So, who else do you have?’ It was crushing.”
And with high-paying clients come some wild asks.
One asked only to be set up with Travis Kelce and Brad Pitt look-a-likes, “You’re very attractive, but do you think you’re Angelina Jolie?” Winston said in response. Another had a list of 15 “must-haves.”
Winston shared that her most successful clients are those who use her services with realistic expectations — even if they have budgets most could only dream of.
Charles, a 39-year-old cybersecurity professional, found his perfect match by following this advice when working with the NYC-based Matched by Quality team, run by siblings Melissa and Nick Rosen.
Though Charles, who declined to share his real name, initially signed up for a coaching package for $5,000, after a few months, he upgraded to a full-blown matchmaking contract, which included six dates in total, “wingman” hangouts, where Nick would personally accompany Charles on nights out, and even hypnotherapy sessions with Melissa, who has formal certification in the practice, for a little over $30,000.
“I work in cybersecurity, so my job is literally patterns and risk. Dating in New York was the opposite of that — a lot of noise,” the New Yorker told The Post. I wasn’t having trouble getting dates, but I kept ending up at the same place.”
Explaining how he would solely chase looks before soliciting matchmaking, “I wasted a lot of time and money on first dates that ended up going nowhere because we had nothing in common besides the initial attraction,” the Manhattanite explained.
“I [decided] to treat it like any other problem — bring in someone who knows the terrain better than you. It was as simple as that.”
But something not as simple was receiving the no-nonsense feedback from the professionals.
“It was direct, even sometimes uncomfortable — like a good trainer, no fluff,” explained the 39-year-old. “Some of the feedback stung, but it was accurate… Like, I didn’t know I was constantly checking my phone on dates until they told me. That was humbling.”
While the matchmaking contract included six dates in total, Charles ended up meeting his now-girlfriend during one of Nick’s “wingman sessions” after five and has since paused his contract, which can be put on hold up to a year. He is currently “really happy with where things are at.”
“I met some great women who were very attractive,” the cyber-security professional noted.“I honestly learned a lot about myself. My [now-partner] keeps me on my toes, but there’s a warmth there I really wanted.”
But not every high-paying client is as lucky as Charles.
After feeling as though she’d exhausted dating apps and was fed up with the “fling culture” of online dating, Hillary LaReau, a 40-year-old Colorado-based emergency nurse practitioner, attempted to find love through Tawkify, “a professional service that would intricately weed through the masses to find serious potential matches that had similar interests and aspirations as me,” the single explained to The Post.
While the company doesn’t reveal its prices online, LaReau disclosed to The Post that she “initially paid $4,200 for three matches. After that was unsuccessful, I decided to buy three more at the same cost.”
“I believed my matchmaker when she said they were working hard to find men that would be a good fit for me, my lifestyle, and aspirations,” the frustrated 40-year-old told The Post.
But after a series of excruciatingly bad dates for almost a year in 2024, it became increasingly clear to LaReau that the screening process was not as involved as she’d been promised — or had hoped for.
“I don’t think there is much ‘matching’ going on — more finding men that met a few requested criteria,” she explained. “I also made multiple requests for them to take their time, but I suppose that would not be good for business. There was very little time taken.”
According to matchmaking vet Amy Doran, founder of NYC’s Modern Love Club, “Dating is such a vulnerable process” that should be handled carefully and thoughtfully by love experts such as herself, especially when clients are paying upwards of $100,000.
Doran, who’s personally interviewed more than 20,000 potential matches over her 19-year tenure for her elite clients, told The Post, “When you’re dealing with high-net-worth clients or celebrities, you want to make good matches with people who aren’t just wanting to be with someone because they are famous or wealthy.”
To find the yin to her prestigious clients’ yang, Doran and her team of 10 do everything from draw upon their personal networks of contacts, scour a singles database, which daters who can’t cough up the cash to become a client may enter for free, throw singles mixers and even recruit attractive strangers while out and about.
She also frequently taps into the networks of her fellow matchmakers — a common practice among the luxury practitioners The Post interviewed.
“Great matchmakers are great collaborators,” said Doran. “If I meet someone, I may be like, ‘I think you’re amazing — I don’t think I have matches for you but here’s this [other person]. That way we can send them to the matchmaker who’s the best fit for them…It’s like trading baseball cards.”
While high earners might’ve found love the expensive way, licensed therapist and author Dr. Kim Van Dusen reassures singles, who can barely afford Hinge or Bumble’s $40 and $50 premium monthly charges, that matchmaking isn’t the only path to love.
“Most experts will say spending over $50,000 on these matchmaking services is the extravagant limit, but I question if this type of financial investment is worth it, especially combined with the emotional investment,” Van Dusen told The Post. “There isn’t a guarantee the relationship will work long-term. If it doesn’t pan out, someone is left without a partner and their life savings.”
As an alternative, Van Dusen suggests singles to seek out “specialized matchmaking events, which can cost between $25 and $3,000, a much more practical option with a lower financial and emotional risk in a higher reward environment, compared to traditional dating apps.”
“These curated, intimate events pre-screen attendees and offer structured activities that encourage authentic connections with others of shared values, lifestyles, and or professional backgrounds,” she added.
And taking up a hobby also can’t hurt.
“I also recommend taking up a new hobby, like a specialized art class, rock climbing, a cooking class, or something of interest that prioritizes your needs and wants but is new enough that you can create an entirely new friend circle and maybe a new love interest that shares your same passion,” the expert continued.
“Worst case scenario is you invest in yourself and make some new friends and learn some new skills that you’ve been wanting to learn.”
