NEW YORK, NY – A man’s attempt to impress his date at a high-end restaurant ended in financial disaster when he unknowingly ordered a $3,500 bottle of wine—after pretending to be a “wine expert.”

Jason Caldwell, 31, had planned the perfect evening: a romantic dinner, candlelight, and the illusion that he was much classier than he actually was. Unfortunately, one poorly timed bluff turned his night into a financial nightmare.

“I just wanted to seem sophisticated,” Caldwell admitted. “I didn’t expect it to cost me my rent.”

According to witnesses, the evening was going well until the waiter handed him the wine list—a 20-page book filled with words he did not understand.

“That’s when I panicked,” Caldwell said. “I didn’t want to admit I usually just buy whatever’s on sale at the grocery store.”

Instead of asking for help, he decided to fake it. He furrowed his brow, nodded thoughtfully, and muttered, “Ah yes, an excellent selection.”

The waiter, clearly impressed, asked if he had a preference. This was Caldwell’s moment to back out—but instead, he doubled down.

“I wanted to sound like I knew what I was doing,” he said. “So I just confidently said, ‘I’ll take the Château Margaux 2003.’”

Unbeknownst to Caldwell, Château Margaux 2003 is one of the most expensive wines on the menu. The waiter’s eyes widened slightly, but Caldwell mistook it for admiration.

“I thought he was impressed,” Caldwell said. “In hindsight, he was probably thinking, ‘This guy’s about to have a heart attack when he sees the bill.’”

The bottle arrived with an entire ceremony. The sommelier carefully uncorked it, poured a tiny sip for Caldwell to taste, and waited for his reaction.

“I had no idea what I was doing,” Caldwell admitted. “So I just swirled it, sniffed it like I’d seen in movies, and said, ‘Ah yes, bold… yet… mysterious.’”

His date, seemingly impressed, nodded in approval.

Then the check arrived.

“At first, I thought there was a typo,” Caldwell said. “Then I realized, no, I had actually just spent $3,500 on fermented grape juice.”

His face reportedly went pale as he considered his options: run, cry, or fake a medical emergency.

In the end, he did the only thing he could—he paid.

“I put it on my credit card and just accepted that I will be living off ramen for the next six months,” he said.

His date, to her credit, offered to split the bill.

“She even said, ‘You didn’t have to impress me, I would’ve been fine with house wine.’ That was helpful after I had ruined my finances.”

Caldwell has now sworn off pretending to know anything about wine. His new policy? “Whatever’s cheapest, please.”