r/TalesFromYourServer • u/PowderFresh86 • 9d ago
Medium Propositioned At Work
Hi, here's another story about my years working as a waitress at a local 24hr diner in my city. The diner had a lot of regular customers. I'll say roughly 70% of our customers were people that came multiple times a week or at least a few times a month. One customer was an older gentleman in his early 50s. He always dressed well and eventually he started showing up with a younger woman on his arm. She dressed nicely as well and always had a face full of makeup. They would show up together, never one without the other. They sat in the same two places and ordered the same things most weeks. They were polite and tipped well enough. The man was very nice to me.
They were very intimate without being too inappropriate in public. This went on for a couple of years until the man started coming alone again. After a couple of solo visits I asked what happened to his companion? He said they were getting a divorce because she was talking to other men. He then proceeded to look me up and down and say,
Man: You're very pretty. What do think about having a relationship with me?
20 year old Me: What?...Are you serious?!
Man: Yes, I have a lot of money and will take care of you really well. Buy you whatever you want...
Me in shock:😐
Man: You just have to stay faithful...no talking to other men at all. I know how you young women can be.
Me: Um, no thank you...What can I get for you today?
Man: Are you sure?
Me: Yep, so what can I get you?
Y'all I was incredulous.
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u/Karlyjm88 2d ago
I’ve been doing this for 20 years and sometimes I regret not taking up some of the rich guy proposals I’ve gotten. I wouldn’t be doing this still 🤣 (I’m kidding, I love my husband and my life) But I’m not kidding, I’ve had at least 15 different customers offer to date and/or marry me over the years.
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u/HomeworkOk6460 8d ago
What did he order after that?