Decades ago, I had what might be one of the most infamous dates of my life. It’s a story that’s as unbelievable as it is unforgettable. Here’s how it all went down.
I had been seeing this guy for a little while, and we’d already gone on several dates. When he invited me out with his friends, it felt natural. He’d talked about them a lot, so I figured it was a good sign that he wanted to include me. He told me to meet him at his house.
I parked my car, went inside, and was greeted by his parents sitting in the kitchen. This was unexpected, to say the least. I had no idea they’d be home, and my outfit—a skimpy but cute look for the club—felt wildly out of place. His parents were visibly surprised to see me, but they politely asked if I wanted something to drink. Awkwardly, I declined and stood there waiting while he finished getting ready. After what felt like an eternity, he finally emerged, and we headed out.
We were getting picked up by his friends. When we arrived at the club, one of his friends assured us that we wouldn’t have to wait in line since he "knew someone." True to his word, we were escorted straight to a table. It was one of Chicago’s well-known clubs, and the setup was impressive. We were a group of eight—six guys and two girls—and everyone started chatting amongst themselves.
That’s when the guy I was with turned to me and said, "Hey, we only have cash, but the club needs a card on file. Can we put your card down? We’ll pay cash, but they just need the card for the tab." I agreed, mostly because I’d seen how much cash they were carrying and assumed it wouldn’t be an issue. The night went on, and we were having fun—dancing, drinking, and enjoying the vibe. Bottles kept coming out, and I struck up a casual conversation with the bus boy who was cleaning up our table. He spoke Spanish and complimented my shoes, which led to a brief, friendly exchange.
As the night wound down, it was time to settle the bill. One of the girls in the group asked me to go to the bathroom with her, and since I needed to go, I agreed. But when I came back out, the group was gone. Not a single person from our party was on the dance floor or anywhere in sight. I asked the bottle service girl what happened, and she said, "They mentioned you were taking a taxi home and covering the bill."
The bill? $2,700—plus tip.
I froze. Then I started crying. I told the bottle service girl what had happened, but she said there was nothing she could do. I tried calling the guy, but he had blocked me. I was completely distraught. That’s when the bus boy, who had seen me crying, came over to ask what was wrong. I explained everything, and he admitted he’d overheard the group talking but thought they were joking. He had no idea they’d actually leave me with the bill or that my card was on file.
What he did next was incredible. He said, "What I’m about to do could get me fired, but this is messed up. I’m going to take your card, and you’re going to walk out through the basement. Exit through the backroom by the trash cans." He handed me my card, and I followed his instructions, slipping out unnoticed.
From there, I took a taxi back to the guy’s house because my car was still parked there. By the time I arrived, it was 4 AM. Exhausted and furious, I marched up to his front door and rang the doorbell repeatedly until someone answered. His mom opened the door, looking completely shocked. I pushed past her, started yelling, and explained everything that had happened.
She immediately woke him up, and soon the entire household—parents, siblings, everyone—was in the living room in their pajamas, trying to figure out what was going on. His mom was livid. She started crying, his dad was yelling, and his siblings were chiming in. Meanwhile, I kept telling them they should all be embarrassed to be related to such a terrible person. The guy just stood there, stunned, mumbling apologies while his family berated him.
It was a chaotic, unforgettable scene—and a night I’ll never forget. Never, ever again.
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Alejandra