‘I Need To Talk About It’: NYC Woman Shows Up To First Date With 43-Year-Old. Then He Has 2 Of His Interns Join Them

First dates can be nerve-wracking, especially for women. They’re used to taking safety precautions before even agreeing to meet. It’s not unusual to share locations with friends, come up with a good exit plan, or keep an eye out for red flags. Because when things go wrong, they often go really wrong.

That’s exactly what happened to Caitlin, a woman in New York City who says she went on the “absolute worst date” of her life.

TikTok creator Caitlin (@centralparkracoongorl) posted a video describing the New York City date. Her clip has already racked up more than 347,100 views.

“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,” she says at the start.

She explains that she met a man at a bar in the West Village. “He was definitely older, which I’m not usually into, but he seemed really cool and nice and well dressed,” Caitlin says, adding that when he asked her out, she decided to give it a try.

The two met at Cecchi’s, a restaurant in the West Village. But when she arrived, she says he wasn’t alone.

“The second I come into the date, I see that he’s sitting at a table with six of his guy friends,” she recalled. Two interns from his company also joined, leaving Caitlin immediately uncomfortable.

He eventually moved them to a separate table, but things didn’t get better. When Caitlin revealed she was 25, she says he told her he was relieved. She recalls him saying 21- and 22-year-olds couldn’t keep up intellectually, while 30-year-olds were “too desperate.”

A Strange Dinner And A Push To Keep The Night Going

As the night went on, Caitlin says the man began showing off pictures with celebrities and talking about the company he had founded.

“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,” she says.

When dinner ended, Caitlin was ready to leave. But he insisted she come with him to an art gallery bar next door called People’s.

“I don’t really feel like going to People’s tonight. It was a Tuesday,” she explains. According to her, he told her he wouldn’t order her an Uber unless she went with him.

She laughed off the threat, saying she could get her own ride home. But he pleaded again until she agreed, she recounts. Inside, she was once again seated with a group of his older friends.

An Abrupt End

The date came to a sudden end when one of the men mentioned that a celebrity would be at the membership-only Chez Margaux later that night.

Caitlin said her date became visibly excited and quickly arranged a car to send her home.

But as she waited outside, she says she overheard something she wasn’t supposed to. A friend ran out and asked, “’Did you get rid of that girl? Let’s go to Chez Margaux.’”

“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,” Caitlin explains.

She locked eyes with both men. “We’re all just looking at each other like that Spider-Man meme,” she remembers. Moments later, her car pulled up, and she left.

How Do You Spot Red Flags On A First Date?

Caitlin’s story lines up with some of the most common red flags women report seeing on first dates.

In a piece for Image magazine, author Hannah Kingston shared results from a reader poll about the most notorious red flags people should look for.

At the top of the list was stinginess. Kingston explained that when someone suggests going out but then seems surprised when money is involved, it puts everyone in an awkward position. Another major red flag? Rudeness toward hospitality staff. As Kingston put it, “I have witnessed the life drain from their date’s eyes” after someone snapped at a server.

Other common deal-breakers included constantly checking their phone, bringing up exes, being obsessed with their job, or failing to ask their date a single question.

And, of course, a few more blunt and amusing ones made the list: arriving drunk, being openly misogynistic or racist, or proudly showing off a Velcro wallet.

Commenters Are Appalled

In the comments, many thought the biggest warning sign was the man’s age. “Girl the biggest sign was he’s 43 and single,” a commenter wrote.

Others said they recognized him. “Airbnb guy – a friend of mine dated him and he’s completely unbearable,” one person said.

Some joked about how far people were going to try to identify him. “Creator: I’m not going to say who he is. Comments: here’s his home address,” another added.

And at least one tried to guess the celebrity he wanted to meet. “Was the celebrity a blonde & was recently in a jeans ad campaign?” a commenter asked, referencing Sydney Sweeney.

BroBible has reached out to Caitlin via TikTok messages for comment.