Dating in New York City is notoriously tough. One woman says a particular type of man in his 30s is nearly impossible to build a real relationship with, and she blames it on timing.
In a TikTok video posted on Oct. 11, 31-year-old Sierra Simon (@sierraasimon) shares a theory about why some men in their 30s seem more interested in partying than in finding a relationship.
She says women spend their entire 20s enjoying the city’s most exclusive bars, restaurants, and venues, while some of these men are only now getting their first taste of that lifestyle. Her video has pulled in nearly 95,000 views.
‘Men in Their 30s in New York City Are Black Holes’
“Men in their 30s in New York City are black holes, and I’m going to explain exactly why to you right now,” Simon says in her video.
She explains that men and women get into the city’s most exclusive nightlife spots in different ways.
“The scene of New York City is very pay to play for men,” she explains. Women, especially beautiful ones, have been walking into members-only clubs and exclusive spaces from a young age, without the financial resources men are expected to bring.
She names Zero Bond, Chez Margaux, and Faena as examples of the places she means.
“We have been allowed to get into these seedy places … easily our entire lives since we were 20, 21,” says Simon. “Which means as a 31 year old, I’ve been in that environment and in that setting for 11 years.”
Men, she argues, follow a different path.
Women get into ritzy spots through their looks or connections, while men typically need money or status.
“So what happens is they work hard, they’re grinding, they start to get their money and they start to realize that they can now pay to play in these places,” she explains, adding that “this really starts to happen [around the ages of] 29, 30, 31.”
‘You’re Basically Just Dating a Boy’
Simon says this timing gap sets men and women of the same age on a collision course. A 31-year-old woman may be all partied out, while a man her age might just be discovering it all for the first time.
“They are basically the level of excitement that us women were when we were like 21, 22 years old being at these places,” she says.
She believes that makes pursuing a meaningful relationship with a man deep into this lifestyle pointless.
“It’s literally impossible to have anything remotely serious, deep, meaningful with the men in New York City who care about being in these rooms,” Simon says.
Her advice to women dating these men is to compare them to their own younger selves.
“That is why they’re scheming, they’re plotting, they’re doing all of these things,” she says. “Because it is literally like a brand new Disneyland for them. And it’s a place that we’ve been in for over a decade.”
Her conclusion is simple: “You’re basically just dating a boy 22-year-old.”
Several men in Simon’s comment section agreed. One wrote, “As a 31 y/o man in tech and based in a major U.S. city, I think this is dead on,” and another added: “As a man that frequents these places – you are spot on lol.”
Is Dating in New York City Harder in Your 30s?
New York City’s dating scene has long carried a reputation as one of the toughest in the country.
Time Out New York ranks the city among the five worst in the world for dating, alongside Los Angeles. A 2025 WalletHub analysis also compared 182 American cities across 35 measures and placed NYC 145th for singles (but 5th for fun and recreation).
Dating in your 30s adds more complications, since people of the same age aren’t necessarily in the same phase of life.
One person might want to settle down, while another is only beginning to enjoy the financial independence or social opportunities they spent the past decade working toward, especially in a city famous for its “fun and recreation.”
Anecdotally, many women on Reddit agree that dating gets harder in their 30s than it was in their 20s. They cite a smaller dating pool, higher standards, and more life baggage on both sides.
Is There Any Hope?
Still, dating in your 30s isn’t a lost cause. A June 2026 Marquette Law School Poll found that single Americans in their 30s reported going on dates more often than any other age group surveyed. So the problem seems to be less about finding dates and more about finding someone who shares your priorities.
At least one man chimed in on Simon’s TikTok, writing “I’m 36 in NYC. I could care less about these types of places.”
Maybe the secret to finding love in New York City is finding a guy who’s already bored of it.
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