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

30. Holy Crap

I once waited on the engagement party of a girl I slept with a week before. I said congratulations.

31. Ditched

I don’t know if this counts as the “worst” date, but I definitely helped a couple not too long ago that definitely took the cake for the most awkward table. They both came in about an hour before close. The first thing the guy does is order a bunch of shots and a drink for his girl. Soon after he orders food for both himself and her. The next time I walked past them, I noticed that he’d moved his chair around to her side and was whispering sweet nothings into her ear. Keep in mind that I was the last server on and the restaurant was pretty dead so it was hard to miss. He kept this up for a while, even when I brought them their food I wasn’t acknowledged.

They’d barely eaten anything when I noticed that they’d suddenly disappeared, but they’d left some belongings at the table, so I knew they didn’t run out on the tab. I immediately assumed that they were in the bathroom boning at this point, so I informed a few of my co-workers that were working on their side-work. One of my fellow servers got ballsy and decided to go to the bathrooms and investigate for herself and found them in the hallway by the bathroom. She said from the looks of it, it seemed as if there was a debate whether or not to actually go into the bathroom. Soon after the guy ended up coming back to the table and asked me for the tab.

Then the guy disappears and the girl is left with the tab. I asked her if I needed to run her card, she seemed really upset, and told me that the guy was going to get a card out of his car. She waited for at least 10 minutes when I heard someone ask for me at the host stand. The guy wanted to pay for the tab but didn’t want the girl knowing he was back. Then he just left. It was so bad and so awkward.

My assumptions are this… guy wanted to get it on the bathroom, girl didn’t, guy bails on tab afterwards, comes back to pay it, then ends up ditching the girl.

32. The Overprotective Father

I use to work at an Italian restaurant on the not-so-great part of my town so the clientele there was always… interesting. But I will never forget when this younger couple came in on a date, that was chaperoned by the girls dad. Yeah totally understandable, maybe even kinda cute if they were pre teens, but no. These two looked like they were soon to be adults, definitely old enough to be on a big kid date. The dad sat himself at this smaller table RIGHT ACROSS THE WALKWAY from the two of them and seriously just stared. Didn’t order anything. Not even a drink. Just watched. It was so cringy seeing the reaction on the guy’s face when he realized what was going on, and how breezy the girl was being. She ignored the elephant in the room but the entire time he had this “could you fucking not?” look on his face. Uggh.

33. Typical Blind Date

Long story short – blind date. Lady was normal woman. Dude got naked in the unisex open concept bathroom during date. Twice.

34. The Things You Hear

My fiance is a waiter. He was serving a couple one time, and he started to approach them later to ask them how their food was, and right when he walked up, he heard the guy saying “And that’s why I’m breaking up with you” and the girl started crying. He backed off a bit to let that diffuse heh.

35. The Bird Savior

I was working a shift out on the outdoor patio of this restaurant located in a harbor right along the water. Happy hour just started and the place is packed, and I’m also training a new server. We are alternating tables when a strange older man sits down in our section with a youngish woman. My trainee takes them, and I hear a play by play of all the weird stuff he is doing: trying to order her drinks and food when she had just met him, and insisting on ordering the most expensive items. All of sudden, he looks out at the first boat docked near the restaurant, directly next to the whole patio. He notices the fake bird tied to the top of the boat flapping in the wind, to scare away other birds that are alive I’m guessing, and immediately decides to run to its rescue. He frantically asks us for a knife and instead grabs a steak knife from the food window.

At that point there are probably over a 100 people on the patio eating, and more inside, who can all see the boat, the not bird and the man. He runs out the exit, around the boardwalk along the patio, then down the docks. He proceeds to break into this boat, climb up to the top, and instantly realizes what he’s done. His walk back was so embarrassing I made my trainee serve them the rest of their meal. His date was obviously traumatized, and everyone in the restaurant had a good laugh.

36. There Was Blood Everywhere

I used to wait tables at the nicest restaurant in not just the town but the whole the area where I lived. Always rated #1 in the state, full of rich people and all that jazz. A couple sits down to order and I come over almost immediately to ask their water preference. The woman goes to scootch her chair in and, within what was probably a 10th of a second but I remember it as if it was slow mo, when she brings her hand back up I notice a spatter of blood go across the table cloth. Her date notices blood. He yells “YOUR FINGER!”. The woman looks down. I look down. Her finger tip, ring finger on her right hand, is gone. Blood is slowly dripping out of the stub and going all over the table. I stand there in shock going “uhh uhh uhhhhhh”. They both stand up and the man tips back her chair. The finger tip tumbles to the floor. He then picks it up and I run to get ice and tell the bartender to ask if anyone is a doctor (there were many) and to get the owner.

Turns out the front corner of the wooden seat had become disconnected from the hollow metal leg. Chopped it clean off. I swear to God to this day I can never scootch in a chair without thinking about it.


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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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