“Acting like that at 43 is the hugest red flag”: NYC woman’s “worst first date” with “egomaniac” goes viral for all the wrong reasons

When 25-year-old TikToker Caitlin shared the story of her “worst first date ever,” it quickly struck a nerve online. Her Aug. 14, 2025, video, which now has more than 365,000 views, detailed her night out with a 43-year-old entrepreneur and “egomaniac.” TikTok users immediately recognized the red flags and rushed to identify the mystery man behind her viral story.

Storytime: Dating in NYC

Caitlin began her story: “About a month ago, I went on the absolute worst date I have ever been on in New York City. And I need to talk about it.”

The 25-year-old met him for their date at a restaurant in the West Village, where he led her to a table occupied by six of his guy friends and two interns from his company. When he realized she seemed uncomfortable at a table full of strange men, her date asked a server to reseat the two of them at a table for two.

Alone at a new table, Cailin said he asked her how old she is. “And when I say that I am 25, he gives me the biggest sigh of relief,” she said. “He tells me that 21 and 22-year-olds can’t keep up with him intellectually, but he feels too bad for 30-year-olds because they’re so desperate, and it makes him sad to be around them.”

“And I should have just got up and left, but I am a little bit of a people pleaser, which I’m working on,” she admitted. Caitlin recalled that throughout dinner, he showed her pictures of himself posing with celebrities. She said, “In the back of my head, I’m just thinking, this is so embarrassing for a 43-year-old to be acting like this is some huge flex.”

Caitlin was ready to go home when they finished dinner, but was convinced to continue the date at an art club nearby. She said her date told her he wouldn’t call her an Uber home unless she went with him to the second location. Although she laughed and said she could order her own car home, Caitlin ended up giving in to his pleas and staying.

“Come with me or no Uber”: The second location ultimatum

At the club, Caitlin and her date joined a table where another group of his friends and older men who knew him were seated. It was “basically a repeat… of what happened next door,” she said. “These guys are just all really close, and I’m just sitting there doing absolutely nothing like a prop.”

Thankfully, Caitlin had the opportunity to make an exit when her date got a better offer—to go hang out with a celebrity at Chez Margaux. He made up a story that he was “not feeling well” and needed to go home, and he called her a car.

As she waited on the street for her ride, she overheard one of her date’s friends say, “Hey, did you get rid of that girl? Let’s go to Chez Margaux.”

Caitlin continued, “And he turns around because he doesn’t realize that the car hasn’t picked me up there. I’m still standing there, and I can hear all of this. And I turn around and the friend looks at me and realizes that I heard everything and has the blankest expression on his face. The guy that I was on the date with turns around as well and we’re all just looking at each other like that Spider-Man meme.”

@centralparkracoongorl Storytime about my date with a 43 year old egomaniac 🤠#peoplesgallery #datinginyour20s #agegaprelationship ♬ original sound – centralparkracoongorl

Caitlin’s “worst first date” resonated with others navigating the dating scene and seeing nothing but red flags.

“Why does it feel like he was trying to show you off to them? while simultaneously ignoring you?? 😭”

“Parading you in front of his boys is a lil weird. But the 25 vs. 30 thing at age 43 is wild.”

“What he really meant to say about 30 yr olds is they won’t put up w a second of his shit lol.”

“Girl, the biggest sign was he’s 43 and single.”

“Airbnb guy – a friend of mine dated him and he’s completely unbearable.”

Much like NYC, TikTok is a small town. Act right, or the Caitlins will come for you.