48 Waiters Share The Most Cringeworthy Dates They’ve Ever Witnessed

25. Ok, This One Is Also Just Super Sad

Had a young gay couple come into the restaurant I worked at about 10 years ago. They were adorable, but about 5 minutes in I think they recognized someone else in the restaurant and the date suddenly became not a date. I guess they were both still in the closet at the time. The rest of their dinner was insanely awkward, never making eye contact and they barely spoke the entire time. Felt really bad for them.

26. Not A Great Way To Remind Someone Who You Are

I waited on a man and a woman who got into an argument at the table, after which the man got up and left the restaurant. He stuck her with the check and apparently he had driven the two of them to the restaurant, as she was waiting outside the restaurant when I left work, waiting on a ride to come.

Jump ahead a couple of weeks, I walk up to greet a table where a man and woman are sitting. I welcome them to the restaurant and ask for their drink order. When I turn to the man, he excitedly says “You were my waitress last time I was here! Do you remember me? I was with the girl and I left her behind?” He was with a new girl this time though…poor girl probably should have left him at this point…

27. WTH?! How?

I was waiting a table for two teenagers who where probably around 16 or so and clearly on one of their first dates. Everything appeared to be going well until the boy got his head wedged in the back of the chair. Fire brigade were called and after 20 embarrassing minutes he was cut free. Girl went to the bathroom and never returned.

28. The “Bitch” Who Liked Assholes

I’ve commented this in a previous post before, but it’s a good story so here it is.

I worked in a bar while I was in college and I had a guy come in before his date and told me that when ever he ordered a scotch what he really wanted was chardonnay. I must have given him an off look because then he got embarrassed and confided in me that he was really in love with the woman meeting him there for the date. He told me how she usually dated guys that were more macho and he didn’t want to order wine in front of her, but if he ordered anything else he would make a face because he didn’t like the taste. I felt pretty bad for the guy so I agreed. He seemed like a genuinely nice man and I wanted to help him out. Well the woman this nice man was in love with was a total bitch.

She came in with two other women to their date, he mumbled something to me about maybe not being clear, and plastered a smile on his face. The woman was extremely charismatic she was one of those life of the party women and the guy was very quiet… Anyways later in the evening he ordered another “scotch”, he had been doing this all night, only this time when I brought it to the table she insisted she wanted to try it. She said that she had never ha scotch before etc etc. It was like watching a train wreck, he tried to stop her saying things like “here let me buy you a glass” etc. well she took one sip and knew it was wine… I tried to help him going over and apologizing pretending it was my mistake, but she guessed the truth and started teasing him. Her friends joined in laughing as well… I felt awful and I could tell he was really embarrassed, even though he was laughing along etc. After a while he asked for the bill, I brought him the tab with his and the woman’s portion and he told me he was paying for everyone.

I felt so awful, the woman and her friends had all had so many drinks the tap was over 100 dollars, but I brought it and he tipped me 50 making me feel if possible more awful. They were my last table so I closed out with my manager and went back into the bar to have a drink with another girl that worked there. The group was still there so I decided to go over and ask to buy him a drink. I just wanted to I don’t know help him or something. Make him look good and possibly make that woman jealous. Well I went over there and asked if I could buy him a drink. He smiled at me, got up from his chair, and took me aside. He told me I was very beautiful, but I was too young to be hitting on men old enough to be my father.

I almost explained to him that I was just trying to help him, but decided not to. I figured that he could use the ego boost after that “date”.

29. A Bad Break Up

Did not wait the table, but I had to clean up the mess. A young couple were having dinner when all of a sudden the guy stood up, picked up his plate of wings and threw the plate at the women’s face and stormed out the restaurant. Turns out she had brought him to dinner to break things off and he did not like that.


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  • http://radiatepositivelife.wordpress.com Natali

    This was probably the most entertaining thing I will read all week!!!

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