Dating in New York City is notoriously difficult. According to one woman, there’s a particular type of man in his 30s who is practically impossible to build a meaningful relationship with, and it all boils down to a difference in timing.
In a TikTok video posted on Oct. 11, 31-year-old Sierra Simon (@sierraasimon) offers a theory about why some men in their 30s seem more interested in parties than in finding a relationship.
She says that while women have spent their entire 20s enjoying the city’s most exclusive bars, restaurants, and venues, some of these guys are only just getting their first taste of that lifestyle. Her video has gotten 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 access to the city’s most exclusive nightlife spots operates differently for men and women.
“The scene of New York City is very pay to play for men,” she explains, while women (especially beautiful women) have been gaining entry into members-only clubs and exclusive spaces from a young age, and without the same financial resources expected of men.
She names places like Zero Bond, Chez Margaux, and Faena as examples of the kinds of places she’s talking about.
“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.”
In the meantime men, she argues, have a different trajectory.
While women gain access to ritzy spots through their good looks or connections, 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, before adding that “this really starts to happen [around the ages of] 29, 30, 31.”
‘You’re Basically Just Dating a Boy’
Simon says that this difference in timing creates a clash between men and women of the same age. While a 31-year-old woman may be all partied out, a man her same age might only just be getting into it 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 because of this, pursuing a meaningful relationship with a man who is involved with this sort of lifestyle is 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, with one writing, “As a 31 y/o man in tech and based in a major U.S. city, I think this is dead on,” and another: “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 had a reputation for being one of the most difficult cities in the country to date in.
According to Time Out New York, New York City is one of the five worst cities for dating in the world, alongside Los Angeles. And a 2025 WalletHub analysis compared 182 American cities across 35 measures, ranking NYC 145th in cities for singles (but 5th for fun and recreation).
And dating in your 30s introduces other complications: People of the same age aren’t necessarily in the same phase of life.
While one person might be looking to settle down, another is only just beginning to enjoy the financial independence or social opportunities they spent the previous decade working toward—especially in a city renowned for its “fun and recreation.”
Anecdotally at least, many women on Reddit tend to agree that dating is more difficult for them in their 30s than it was in their 20s. Some reasons listed include a smaller dating pool and higher standards, as well as more life baggage from both ends.
Is There Any Hope?
However, dating in your 30s isn’t completely hopeless. 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 issue seems less to be about finding dating opportunities, and more about finding someone aligned with one’s priorities.
At least one man dropped into the comment section of 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 dude who’s already bored of it.
@sierraasimon
Subplot reached out to Sierra Simon via TikTok message.
