Parole Officers And Broken Bones: 13 People Share Their Worst First Dates Ever

First dates can be so exceptionally awkward. It’s like a job interview for a job you’re not even sure you want. You’re out with someone you don’t know well, aware that the night could turn into something romantic and wonderful, or boring, or worst of all, just plain awful. Sometimes the awfulness is funny, though — maybe not at the time, but looking back. These Redditors shared their funniest worst first date stories, and while the dates were certainly terrible, the stories are hilarious.


1. ChoppyChug was zero for two right from the start.

I met up with a girl I’d met on OKcupid, we had planned to go to this little coffee shop. I get there about 15 minutes early and find that the place is closed inexplicably. I then return to my car to find out I had locked my keys AND phone in my car.

So I had no choice but to just sit and wait for her to show up so I could explain to her that the place is closed AND ask her to help me get my keys out of my car.

2. Molly-Millions‘ date bared it all. Not his all, but his ex’s all.

Went on a date with a guy I’d met through a mutual friend. Things seemed pretty normal until we were sitting and waiting for the movie to start. He got his phone out and started showing me pictures of two of his ex-girlfriends. Both women were completely naked.

3. There is no explanation for the behavior of brokebackhill‘s date.

A cute-ish guy approached me at a foreign film screening at my university in Arizona and asked me out in French, which was the language of the film. I spoke college level French, so I accepted the offer of a date. I mean, he was kind of cute.

When he picked me up that Friday night, he greeted me with “Guten tag!” Okay, cute, a reference to the foreign film screening, right? Nope. From that moment on he spoke nothing but clumsy German all night long. He took me to Blockbuster (I’m old) and we rented a German film. He spoke German to the cashier. He spoke German through dinner. He spoke German while watching the film. He tried to get to first base in German. And yes, this whole time I was telling him repeatedly that I don’t speak German, I can’t understand him, etc. He just responded in German.

But the weirdest moment was when his roommate came home as I was awkwardly leaving (my date was trying to convince me to stay, in German) and my date interrupted our “conversation” to say in a perfectly normal Arizona accent, “Hey man, what’s up?” And then turned beck to me and continued to speak German. Oooooookaaaay.

4. Ridiculous_Diagnosis might have had the worst first date in the history of dating.

I took him to a baseball game, where he proceeded to pronounce loudly to anyone and everyone around us that we were an “item”. He pulled out a very large bag of peanuts with the shells and started eating them…with the shells still on. He had pieces of shell all over his face while he kept asking my friends if they wanted any, occasionally spitting up nut particles on them much to their horror and my extreme embarrassment.

He then tried getting into a full on fight with me about a hypothetical situation where we would be caught on the kiss cam. “I’m just saying, if we’re on it we gotta go HARD!!” And I was just sitting there cringing and grinding my teeth into oblivion.

He drank so much that he never really even saw the game (had to keep getting up to go to the stadium bar) and he kept asking for my ID so he could double fist his 10$ coors lights. He probably spent 100$ on coors in the first few hours. Not sure why I kept letting him use my ID, maybe it was just shock.

He chugged 2 beers on our way out and kept refusing to let me walk on a certain side of the sidewalk because “a man walks on this side, it’s his duty to a lady”. Wtf. He started insulting women as we were walking past to get to my car. I was ready to punch him in the mouth but he was 6’7″ and I just wanted to take him home and forget the night ever happened.

He drunkenly started insulting my driving while we were in post-game traffic and kept trying to open the door to get out and drive instead of me. He insults my career, tells me I couldn’t possibly keep up with the “manly” job I have, but dont worry babe it’s not because you’re not great, it’s just that it’s too hard for you is all I’m saying.

I finally pull up to his house and I’m white knuckling it to the point where my hands are nearly numb. I tell him to get out and he asks me to come in. I say absolutely not and he lunged at me to kiss me. He like…sort of….licks? My face? And I literally shoved him out of my car onto the street and sped off.

The next day he texts me, “hey had a great time! Would love to see you again!” I said “your behavior was ridiculous, please never contact me again.” And he responds, “cool, well if you ever want to get a beer let me know! ?”

Hard pass. Hard. Pass.

Edit– TL;DR: guy spits peanuts on my friends, gets drunk, insults me all night, licks my face.

5. Just shaking our heads at FloppyTunaFish.

Backed up into her parents car on our way out causing 1,500 dollars worth of damage.

6. Three was a crowd for PM_ME_TINY_DINOSAURS.

I was talking to a guy online and we finally agreed to meet for a date.

I get there and there is a woman sitting with him. It turns out that it was his wife and they were looking for a “third”.

He never mentioned that during our chats and then called me a cunt for saying that I didn’t want get involved.

7. FeeingWhimsical‘s date resulted with her leaving Tinder altogether.

Finally get to share this story!

A couple of years ago I dabbled a bit with Tinder. Met one guy who was super cute, traveled a lot, and seemed interesting. I suppose “interesting” was one word I could use to describe him.

We start the date by getting lunch and a few beers at my favorite spot in town. We were chatting away and the topic of daydreaming came up. I asked him what he daydreamed about.

His eyes then get a bit dark and his voice gets low as he says, “When I daydream, I imagine the light leaving my enemy’s eyes.”

By this point I was a few beers in and didn’t know what to say. I respond with, “Oh…so uh, how do you do it?”

He looks away, ponders for a second and says, “Harpoon.”

The rest of the date was spent with him talking to me about his extensive anger issues and how he still lives with and bangs his ex. Hell, he had just banged her before he came to meet up with me.

That was when I decided to stop using Tinder.

8. Iamnotyourbanana probably still cringes thinking about this.

I was so nervous I threw up on him and myself. No second date.

9. IAMATruckerAMA was not met with excitement.

Realizing that I was the guy who’d gained too much weight since his profile pic was taken. At least her look of disappointment motivated me to lose 40lbs.

10. Ouch, mypoorbrain. Ouch on so many levels.

I went on a Tinder date in January that went poorly. At the end he tried to kiss me so I dodged, tripped over a curb, and broke my fibula while falling into traffic. The guy got down in the road with me, moved my hair behind me ear and said “we could tell people that we fell in love”.

11. Let’s just say Nikx‘s date had some issues.

It was just an awkward date with no chemistry, but when he dropped me off near my apartment he asked if I’d like to go on another date sometime.

I tried to let him down easy, but he freaked out and wouldn’t accept it until I explained why I wasn’t interested. Nearly an hour later I finally told him that even if I had been interested, he ruined it by being creepy. Then he let me go.

It’s been 10+ years, but I’ll never forget the last thing we said to each other. He asked “Will I ever see you again?” And while scurrying away, I responded “Only time will tell.”

12. At the very least the date could have asked handsupamazing if she had any laundry, too.

Instead of taking me to dinner a guy took me to his parents house so he could do laundry.

13. Wanderingstorm believes in second chances but yikes.

Met a guy online who missed our actual first date because he had to meet with his parole officer. I gave him a second chance because everyone deserves a second chance and maybe he’d learned his lesson. First time meeting him and I casually ask him about what he’d been in jail for – and he says a drug charge. Okay…not terrible. Then he proceeds to go on and on about how he doesn’t care that he went to jail, doesn’t care if he goes back, etc. Yeah………….bye…….

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