Ruin My Week
21.
“Not a 1st date but a guy decided to propose to a stripper from Scores (high end joint in NYC), she was stunning. Also in fine dining, he gets on one knee and pops the question and she goes out loud “are you f*cking kidding me”. He got up and asked for the check.” –Pieniek23
22.
“Saw a guy hitting on a girl and buying her drinks for the entire night, then realizing she was a hooker.” –ViperKira
23.
“I used to work at a Mexican restaurant and one year when I was working on Valentine’s I was subject to one of the weirdest first dates ever. A couple walks in, she is dressed to the nines, like she’s ready to hit up a club. He is dressed more casually, in jeans and a button-down. Our hostess seats them and when I go to greet them the man announces that this is their very first date! The lady looks less than impressed and gives a small smile, more like a grimace. They order drinks and as I’m watching their table you can tell that the date is not going well. The guy is talking animatedly and the girl is glancing around like she’d rather be anywhere else. I head over to take their order and it’s clear that I’ve interrupted something. The guy looks a little embarrassed and sad and the girl looks pissed off. He orders his meal and she flippantly orders something (seafood enchiladas) without really looking at the menu. She tosses her menu in my direction and sucks down the rest of her drink. I deliver their food and go back behind the counter to continue rolling silverware and watching my tables. They dig in and the man seems to be enjoying his food, his date looks disgusted and is flicking bits of her dinner around the table/floor. I walk over to check in and see if she maybe wants to order something else. I get to the table to ask how everything is and she gets up, SCREAMS that her food is DISGUSTING, and goes OFF about how shitty this date was. She started yelling at him about how he should have ordered for her, how dare he take her to such a low-class place, she was so done with this, blah blah blah. She shoves her plate away, gets up, and storms out of the restaurant. The dude is mortified. I tell him I’ll be right back with the bill and would he like his food boxed up? This fucking guy shakes his head, pulls her plate towards him, and says nope, he’s fine to continue eating the meals he’s paid for.” –TheTrickyLettuce
24.
“There was a guy who would used the place I worked at as his go-to. Every time, a different girl. And every time it ends in anger. He’d butter them up, brag about himself and talk about how he is such a gentleman for treating them to classy place and as gratitude they should let him f*ck them. Every time the date would walk away and we would have to deal with the horny asshole who tried to get either pity sex or pity dessert from the female staff.” –illogicalfuturity
25.
“I was the one on the first date. Went to a bar with this guy, our waitress came up and immediately recognized him, was super friendly, took our orders and left. While she was gone he told me they used to date. The rest of the night they openly flirted with each other. There was no second date.” –1927co
26.
“Wasn’t the waiter just a nearby patron with good hearing. They were just about done with dinner when she gets a call tells the caller she isn’t busy and makes plans to spend the night with another guy all while lover boy sat across from her with his jaw on the floor.” –Not-an-Ocelot
27.
“At the end of the meal… after appetizers, two of the most expensive entrees, a high priced bottle of wine, and dessert with a bottle of Dom… the man says to me, in front of his date, “Hey man… we are on a first date. What more can I do to guarantee I get laid tonight?” The young lady turned deep red with her jaw dropped open. I sat down the bill and said, “After asking me that? There is nothing you can do.” –akoontz
28.
“Restaurant in Canada; a couple come in from USA. Man has a first-gen iPhone and they haven’t been released in Canada yet. Guy at next table is so enthralled with the device he won’t stop talking to the iPhone man. Talks so much that his date, got up without saying anything, and walked out the door.” –ThePalerKing
29.
“Went with my friend to this Italian place we used to go to all the time in high school, and this single guy comes in and sits down at a table for two and looks around and at his phone like he’s waiting for someone. At this point, I’m not paying really attention, but he orders two glasses of wine. About 10 minutes later I’m halfway through my meal and his date (or who I assume was his date) finally arrives and sits down without saying a word, and neither does he. (Btw, I’m not watching their every move, I can just kinda see them when I stare straight ahead. As far as I can tell, after five minutes they’ve said nothing and just drank their glasses of wine). As high schoolers do, my friend and I started coming up with possibilities of what this could be, whether a first date gone horrible wrong or something. I mean, these two 20 somethings were sitting and eating like old people do when they’ve run out of things to talk about after being married for 40+ years. Anyways, they both order ravioli. It comes out wickedly fast and almost immediately, this guy starts to eat it WITH HIS HANDS. Now, I’m really paying attention. By now, they aren’t o have exchanged a few words, but with completely blank faces. Absolutely no idea what they could have been talking about, but the woman hasn’t touched her food at all, and this guy’s licking all the sauce off his fingers one after another. Something like ten minutes went by and the woman still hasn’t touched her food. My friend and I are convinced that this woman is trapped on the worst date of her life, when suddenly, she ALSO BEGINS TO EAT WITH HER HANDS, and grabs a huge ravioli and sucks it down with sauce all over the place. My friend and I are stunned. We can’t make heads or tails of whatever the hell is going on. All in all, I guess they were made for each other. They then ordered desert- some sort of tiramisu- and ate it with forks.” –sderou20
30.
“I waited on a couple who were clearly on a first date, and the lady was clearly not impressed by the guy she was on the date with. The date was over quick enough and the guy paid, leaving me a 5% tip. The next day, the lady came into the restaurant, walked up to me, said “that was the worst first date I’ve ever been on, and I was mortified when he stiffed you on the tip” and then handed me $20.” –Vomiting_Winter
