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

37. “Changed My Perspective”

One night I watched a couple order a pizza and a couple drinks and just eat in silence. they were in their fifties and seemed like they were probably married. I said to my coworker, “man, I hope i never end up in a marriage where I just sit across the table from them at a restaurant with nothing to say.” My coworker said, “actually, that’s the kind of marriage I want to have. one where you don’t have to impress each other or make small talk. Just exist peacefully together.”

Changed my perspective.

38. *Cringe*, Another Proposal

I had man come in for dinner (I work in a four star restaurant) sweating bullets from the time he sat down. He and the lady were obviously a couple and the entire staff guessed what would happen, especially after he ordered a $300.00 bottle of champagne to start the meal. She looked happy, but worried through the entire meal. When the dessert came he got down on one knee and I heard her say, “Please don’t.” Those two words stopped MY heart, I cannot imagine what this poor dude was going through. They had a hushed conversation and she ran out, literally ran, while he sat there still holding an open ring box. He finished the bottle of wine they had ordered during dinner, and pretty wasted turned to me and asked, “Why won’t she let me love her?” Just like that. Like I am going to give him some kind of answer to explain the complex and painful thing that has just happened. I told him that sometimes we fall in love with the wrong people, and the only people worth anyone’s time are the ones who give back what they get. He finished the bottle, paid his tab and walked slowly to the parking garage. I never saw him again.

39. The Freaky Couple

I was probably about 24 waiting in a 4 star restaurant in Cary, NC when a young couple comes in and is seated in my section. As I wait on them the female is quite obviously making moves on me and flirting like there is no tomorrow in front of this guy. I am friendly and joking but never let on that I think she is really really hot. They try to make it clear that they are just friends so I turn on the charm a bit. That is when the guy asks where the bathroom was. I point and give directions but he wants to be shown. After we are about 20 paces from the table he informs me that they both would like for me to come home with them.

Uh, twice the amount of people I wanted to have sex with from this table and politely decline. He goes to the bathroom and when I come back from the kitchen they were gone. $100 tip was on the table and it was an interesting experience over all, just not my cup of tea. She was mega hot, a real bombshell.

40. The Slutty Army Wife

Bartender at a dive bar for a bit and this was the worst thing I saw. Not really a “date” but close enough.

This lady, about 30 or so, would come in every so often and meet men. They’d get drunk and then leave together. Turns out she was new to town so all the local men were interested in her. After about 9 months of this she comes in with a bunch of girlfriends. I’d only seen one of them before so I’m surprised they would come to this bar for a girl’s night out or whatever. We had a small party room in the back and they had claimed it for the night. After about an hour of casually drinking a group of people come in, a few older men and women, a few younger people I assumed were not 21, and finally a man in a military uniform. The man asks around for the woman and a friend of hers says she’s in the bathroom. He asks me where the men’s room is and I see the main bathroom was occupied so I pointed him down the hallway to the bathroom most people don’t use because it’s kind of hidden behind the party room. He thanks me and proceeds to the men’s room.

Next thing I see is the woman running out of the bar and the military man bawling his eyes out to an older guy who I assumed was his dad. After the longest 5 minutes of my life they all leave, a friend says she’ll come back for the tab later that night.

About two hours later one of the female friends comes back in to pay their tab and she tells me the friend didn’t know her husband was coming back from Afghanistan and they wanted to surprise her. Since she’d been going to my bar a lot they thought it would be a great place to surprise her. Turns out she had been having sex with all the regulars in the hallway bathroom for months and never told anyone she was married.

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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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