A Gen Z woman’s TikTok recount of her date with a self-aggrandizing 43-year-old quickly became shorthand for modern dating gone wrong

24 August 2025

In a tale that has Gen Z dating culture binge-watching in collective horror, a 25-year-old New York City woman named Caitlin has sworn off first dates after recounting what she calls “the worst date I’ve ever been on” in a TikTok video that has since gone viral. With over 400,000 views, her story is fast becoming a teachable moment and a meme-worthy cautionary tale.

Caitlin set the scene by explaining that she had agreed to meet the 43-year-old man after a chance encounter at a bar in the West Village. He seemed charming, stylish, deeply confident, and most alluringly not her usual type. So when he asked her out, she thought, why not. Yet just one week later, the evening started sliding sideways. He had deliberately invited six male friends and two interns from his company workers, not dates into their meetup. She walked in, voice trembling with disbelief, only to wonder how a “date” turned into a group outing from match.com nightmares.

Thankfully, he sensed her discomfort and shifted plans, requesting a table for just the two of them. But any hope of redemption evaporated once the real show began. He asked how old she was with an audible sense of relief when she said "25." “21- and 22-year-olds can’t keep up with me intellectually,” he mused, “and 30-year-olds are so desperate.” At that point, Caitlin thought she might collapse into her shrimp cocktail.

The cringe crescendo built as he flicked through celebrity photos on his phone, boasting about encounters and selfies like a human press kit lights, camera, ego. As she tried to unwind, the date's insecurities took over the table when he declined to order her an Uber home unless she extended the night with him. Caitlin managed to politely decline, but her mood only darkened when, waiting for the Uber, she overheard one of his cronies ask the fateful question, “Did he get rid of that girl yet?”

Viewers didn’t salvage the evening they rallied behind her. Commenters lambasted the man’s behavior as performative, emphasizing that his date appeared more like a prop to impress his male friends than a genuine person. “He just wanted to impress the men,” one wrote. Another echoed, “You’re too gorgeous not to have stronger boundaries.”

Caitlin’s TikTok drew parallels with other viral dating horror stories. It mirrored the saga of an Australian influencer who cancelled a potential relationship because the man refused to pay for her coffee an incident igniting debate about dating expectations in the age of perceived entitlement.

Yet Caitlin’s chronicle carried extra weight because of its place in the modern dating landscape. Gen Zers, raised amidst the frenetic ups and downs of social media, swiping culture, and performative romance, are more attuned than ever to red flags and even better at broadcasting them. Stories like hers tap into a deep shared frustration about entitlement, lack of respect, and the rise of male narcissism disguised as mystique.

It’s not just about one disappointing evening. It’s a marker of a cultural moment where ghosting was once the worst offense and now flat-out emotional gaslighting makes the headlines.

As that TikTok circulated, fellow Gen Z-ers piped up with similar experiences like one user whose date whipped out his mother’s credit card when the bill arrived, as if cash were a fashion statement. Another critique: generational texting hints that older generations’ formal norms can feel cold or uninterested to younger daters craving clarity and connection.

Still, amidst the death-by-cringe, Caitlin’s story underscored resiliency. In a digital age where humiliation is shareable and instantly sourced for approval or outrage, her willingness to speak up and walk away earned her not shame but solidarity. Social media users applauded her voice: “At least you know what you don’t want,” one wrote, affirming that a bad date is often the clearest lesson.

So as she swears off “dating” indefinitely, what Caitlin actually reminds us is how valuable authenticity and boundaries can be. If one cringe-filled date can spark so much conversation, maybe it’s time the culture of connection catches up.