32 Food Service Workers Describe The Awkward, Ridiculous Dates They’ve Waited On

4. Not the waiter’s fault

My boss / head server of the restaurant I work at had a similar story.

She had a guy who would always come in with a lady and get a specific bottle of wine; very predictable. One night, she went to greet her table and noticed it was the same guy, so she started off with “Hey there! A bottle of Juan Gil tonight?” Then, she noticed he was with a different woman than usual, and he apparently gave her some non-verbal cues. She tried to play it off by adding something like “I just love recommending that one, it’s one of my favorites!” I don’t think she ever asked or found out which one was the mistress, or if that was even the situation.

Even I had a similar awkward situation one time. As I went to greet a table of two, I recognized the guy had just come in recently (just a few days back), and I said something like “Hey, you look familiar!” Then I turned to the girl. Silence. I clearly remembered he had come in with a brunette last time, and this time he was with a blonde. I smiled awkwardly and changed the subject. He left me a pretty bad tip, so I think I might’ve ruined his date accidentally. Not sure if he was cheating, or casually dating and stopped seeing the previous girl, or if one of the girls was just his sister, or what, but yep it was pretty awkward.

5. Wow, just wow

I used to be a waitress in a diner. One day a young man comes in and sits down. He’s smiling nervously. I go over and ask him what he wants to drink. He says water, and I go get it. When I drop it off and try to take his order, he tells me he’s not ready to order because he’s waiting for someone. Ok, I say, and wait for his joiner.

After about 10 minutes, he confesses to me that he was meeting a girl there. So he could break up with her. He was the only customer in the place at the time, and I immediately thought ‘oh no!’ And wondered how this girl would take it.

A few minutes later, here she comes. She’s smiling, SUPER happy to see him, and comes and sits down as if its her best day ever. I felt awful. I knew in just a few minutes, her whole day is going to shit. It was awful.

She orders him a sandwich, and something for herself. He didn’t want the food, but she was kind of insistent. So, right after I drop off the food, the hammer drops. She’s upset, crying, etc. She tried very hard to keep it together in light of what was being told to her.

After about 30 minutes, he gets up and leaves. She spends a minute collecting herself, and then comes to the register to pay. FOR BOTH MEALS. Yep, he broke up with her, and left her with the bill.

I looked at her teary red eyes and told her to forget it. I paid for it. I just couldn’t bear to watch her pay for his meal.

6. Don’t yell at waiters

I was waiting on a couple once, had to be a first date. The guy was constantly a dick to me, and the girl was very apologetic. He asked for a well done filet mignon, when I started to advise him that it would be burnt as such and to ask if he’d like it butterflied, he he flipped his shit yelling “you don’t tell me how I like my steak!”

She got up, pulled out a $20, handed it to me, and walked out without a word. He shouted after her to come back, didn’t even get up till she was out the front door though. What a douchenozzle.



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