13 Funny First Date Stories That’ll Make You Crack Up
We went out to eat at a steakhouse she insisted I drive her Camaro , where she berated the waiter so badly and for such a trivial reason that I found the manager while she was in the bathroom and apologized. We had time to kill before our movie, so we went to a bookstore. While at the bookstore, I mentioned that at some point I needed to go to a store and buy some beer see reason above. We agree on a restaurant in another, distant-ish part of the city, and dude decides he wants to walk there instead of taking the subway. Though my boots have annoying heels, I try to be a good sport and agree.
He insists that instead of dinner, he absolutely HAS to take me to his absolute-favorite-in-the-whole-world gelato shop, which just happens to be a couple of blocks away. I turn away from dude to look at some display of artisan chocolate or something and surreptitiously gnaw my hand. He takes that as a positive sign, I guess. Dude ushers me, still stunned, into the tiny little corner onto one of the tiny little stools.
He takes the other stool, and then puuuulllllls my stool closer, right between his knees. He feeds me gelato. He actually presses the spoon to my closed lips until I open my mouth. At this point, I busy myself with drinking water to avoid being fed further spoonfuls of gelato and fake an emergency phone call with a nearby friend. I make my excuses, and run out of there to her place, where I manage to obtain real food and booze and laugh and cry and laugh. We made arrangements to meet at a stuffy Cambridge watering hole.
And she was not happy about it! I, on the other hand, was mortified. This fraction of a second set the tone for the rest of the evening which was to be predictably brief , and we soldiered our way through a single drink together which as I may have mentioned was actually my second, thank god. She was not only visibly displeased with our little arrangement but went out of her way to make this as evident as possible: In short, it was the most excruciating half hour of my professional dating life.
As soon as we both realized there was most certainly not going to be another round she started angrily protesting the inattentiveness of our actually perfectly attentive waitress I guess because I was so off-putting that the bill had to be paid RIGHT NOW and she got up and stormed off to the bathroom. So we walked out together. Meanwhile, the train pulled into the Kendall Square stop, and in brief flash of genius I hatched an escape plan: He sang songs on my answering machine, either telling me how he deserved another chance or telling me what a huge bitch I was.
I met men who told me they were single and then three dates in told me they were married. I met a man who said he was 45 but was probably Since I am the common denominator in all these disastrous dates, I think the problem is me. I must have had a terrible screening process. We met at a bar, and she was super attractive I really wanted to bang her but also wanted to be a gentleman so I deferred to conversation. We talked for 6 hours. She came over to my place on that weekend where some friends and I were having a fire.
She texted me at 2AM from inside my house asking if she could stay over after taking her friend downtown. She stayed over and we had awesome sex. We continued having awesome sex every day that week.
And we actually had a lot more in common then sex. Like birds and stuff. Then she mostly disappeared. She wrote me a big ol email about being busy for a while she was finishing her thesis and I was dumb in ignoring the writing on the wall. And this book on the history of graphic design that she said was her favorite. A few weeks went past, and I emailed her to see if we could meet up to exchange our stuff. She had my binoculars. Then she moved to Iowa with my fucking binoculars. But I still have her pillow and book. But not the panties. They had stains in them. But I would totally have negative sex can you do that?
So when I go to leave and his girlfriend current? It was very dramatic.
The atmosphere and food were great! The company not so much. We leave, he then asks me back to his place. I decline and hop in a cab and head to a dive bar to meet up with my friends and tell them about the date. A few days later I receive a text about how ungrateful I was for a great meal and the least I could have done was put out. I was the snob and I totally missed out on being with a great guy who could have provided me financial security blah blah blah.
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I then received a barrage of text messages, each more vulgar than the last. I was a whore, slut, cunt, bitch, fag, gold digger, trailer trash who fucks for tracks His words not mine. He grills me from across the room, and my current boyfriend has exchanged words with him on more than one occasion. He was in an ugly homemade tshirt that loudly proclaimed his religious preferences to the world in about 12 different fonts and 13 different colors.
I was in a denim skirt and summer blouse. He seemed rather needy, but not awful. We said goodbye after the film and he vaguely mentioned doing something the next day. I told him I usually used Sundays to run errands and the like. By the time I pulled out of the parking garage, I had a text message. Four more text messages by the time I made it the 30 minute drive home. After church I forgot to turn my phone back on until I got home from the gym around 3pm.
During that time I missed 17 text messages, 5 phone calls and 3 emails. The entire missive expressed again and again how compatible he thought we were and how amazingly well he thought the date went and how I had to go out with him again. I sent back an email with a single line: We went to a martini bar on Bowery and proceeded to have three i think pretty damn strong drinks.
We got in a cab to go to her place, and attacked each other in the back seat of it, groping a bunch. We got back to her place, and she asked me up.
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I declined, on account of it being the first date. At first, things seemed normal: All the standard stuff. However, as the night went on, Joe started pulling tricks from The Game. Things took a turn for the the what-the-fuck when he started asking to touch my butt and for me to touch his dick through his pants. After about half an hour of being shamed for being boring, I tried to do so, but no luck: I am physically incapable of taking a proper ass shot.
I was happy about this, to be honest. After some mediocre doggie style because I was not going to be face to face with a laughing old man while being fucked by a younger one , I made my escape. I had had my first adventure in Single New Yorker-dom! And it was done.
Or so I thought. PSA for the dudes: So I go to check out his profile, and am smacked in the face by his photo.
He is the identical twin of a good friend of mine. Turned out that he was involved, in varying degrees of seriousness, with a whole bunch of other women many of whom he met online! He seemed really normal when I first met him in real life, too.
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During the post-coital lounge, he told me that he had asked me out again only because he was curious about how I would react, because I seemed so strange. Anyway, we finally go out I pay and also drive to the other end of town to pick her up. I ask her out again and she says yes I paid and drove again.
Again a 3rd time at a really nice place for her birthday yup, I paid and drove. Again a 4th time we split the bill but I still drove. And still not even so much as a kiss. I mean, like, FIVE calls from his mom. He had been divorced for over a year, but still super bitter about it. No excuses on my part for why I kept talking to him. He got married 4 months later, and then had a kid. He tried chatting with me online a few times after those things occurred to tell me he acted the way he did because he was scared of the things he was feeling about me.
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