24 Restaurant Workers Shared The Most Painfully Awkward Dates They’ve Ever Witnessed

14.

“As one of the closers, if anyone came in between 9:00 p.m. and 9:30 p.m., it was no big deal, but I’d make it obvious we were closing at 10:00 p.m. Anyone in after 9:30 p.m., I’d tell them the kitchen closed in 15 minutes. After 9:40, I’d just tell everyone that food was to-go only. The managers didn’t like this, but I was the first to greet the people, and I was doing all the work in that last hour; I was the captain now. So a nicely dressed guy came in at 8:45 p.m. and asked for a table for two. He declined anything but water until his date arrived. I did what I could to stay busy, but after 45 minutes (and it being 30 minutes until closing), I approached and warned him that the kitchen would close in 15 minutes. He said his person was walking in. A woman in yoga clothes walked up and flopped down opposite him, never looking up from her phone. He ended up having to order for both of them because she was not present beyond physically being at the table.”

“I got the order in, and as I was passing to get to another table, I heard him quietly pleading that she give him a chance. Their food came, and as I was dropping it off, she said, ‘It’s just not the way I thought it’d be, so I don’t want to do it anymore.’ His face was crushed, and his body language said he was flatlining. I automatically brought boxes with the check, as she hadn’t touched her food, and I wanted to save time. 

I knew dessert wasn’t happening, but the manager was out front, and I had to try that final upsell or be banished to the back section with the flickering lightbulb. ‘Just ask if they want dessert! Just ask if they want dessert!’ I said it the whole way to their table, and with a giant smile, I asked, ‘So guys, you thinking about DIVORCE tonight?!’ Cue my horrified gasp, and the girl just looked up at me from her phone and said, ‘See Justin? Even the waitress knows this isn’t working.’ And poor Justin just looked at me as I tossed the checkbook and boxes and said, ‘I’m so sorry. Jesus!’ The manager gave them a discount, and I never again offered dessert.”

—Winter-Nebula83