Dating is odd. Sometimes you hit the jackpot, but most of the time…well, you know.
AskReddit users were nice enough to share their most cringeworthy date experiences for your reading pleasure. Share yours in the comments!
“Met with a girl in a dark university bar. Everything is going well. We eventually go outside because there is a mechanical bull we are goin to try. As soon as she gets on the bull, I realize she is at least 10 years older than she claimed and has a rotten meth tooth. After asking her a few questions, she admits that she has two kids outside of the state and has no interest in them.
She also admits to having a girlfriend with whom she is not sexual. She is physical with her though. She starts showing me pictures of her girlfriend with bound breasts…like ropes around them bonding them. This girlfriend of hers is white, but her breasts are black from being beaten in while bound. I was young and completely unprepared for this. We ended the night early and I even got the courage to tell her I wasn’t interested instead of ghosting her like I truly wanted to do.”
2. He knew she was a keeper
“Probably the 2nd date with my now wife. Some guy paid me to get revenge on a buddy of his and wanted me to scatter a few hundred pounds of potatoes into his buddies front yard. It was near where I was planning on taking my now wife and she said she would be cool with helping. So we drove to this guys house, made sure he was not home, filled his yard and driveway with potatoes together then went on our date.”
3. Meet my father
“I went on a date with a guy named Dan when I was in my late teens. Dan said “I’d like you to meet my father, he’s going to love you”
So I got in the car and as we started heading out of town I asked where we were going and Dan said “you’ll see, we’re almost there”
15 minutes later we pull I to a cemetery and he says come with me, I was nervous as I followed him down a little hill and he kneeled down in front of a tombstone and said “dad, she’s going to be my wife someday”.
That was the first and last date Dan and I ever had.”
4. Two tales
“I will tell about both worst weird, and best weird because, I can’t really pick one
Worst weird was this guy that was a avid hiker like me, and suggested we do a quite easy, very known and travelled circuit by the coast. The weather was great ( sunny, windy, the very best for a hike) but.. The guy spend the three hours of the circuit reciting BY HEART all the people having committed suicide on the path ( a part of it was near a cliff so people used to go Sprotch when they wanted to cancel their subscription to Life ™ ) and he knew. Just. So. Many. I mean, it was odd at first, creepy soon after and quickly descended into terrifying. Needless to say no second date was had.
Weird cute one was with a guy I dated for some time after: we were just sipping coffee on a bench when his phone went off : his brother’s wife had gone into early labor and said brother was freaking out, and in his soon to be a dad way ahead of plan frenzy, shouted: ” the baby’s room isn’t even painted!”. Cue my date leaping in with a ” I got this, stay with your wife!” , pocketed his phone, turned to me and went ” I have a double of his keys.. wanna help me paint the room ?”
“What, like, now?”
And we spent half a day painting a kid’s room. That was fun, all things considered!”
5. Don’t tell anyone you’re a mechanic
“I have a bad habit of telling people I’m a mechanic too early into knowing them because I really enjoy it and I like talking about it. The last date I had involved about 20 minutes of us actually talking to each other about things like school, what books we’re reading, and video games. When we get to the part about what we do for a living, I tell her I’m a mechanic. She immediately drops all conversation and begs me to go fix her car right then and there.
I’m a little too nice of a person and couldn’t say no at that moment, so we pay for our drinks and leave. As soon as I see her car I know I made a mistake, it’s been recently wrecked and should not have been on the road. She then starts to tell me about how a friend of hers says it only needs a few repairs and it should be good to go, when in reality it probably should have been totaled with how bad the front end was caved in.
I tell her this and she starts yelling at me saying I must not know what I’m doing, then says I need to fix it anyway and that she needs to borrow my car to go run some errands at 10:30 at night. I tell her no, and that I’ll call her a tow truck since I have AAA, and that I don’t think we’re going to work out. It’s been 3 weeks since then and I still get calls from her asking her what’s wrong with her car.”
“I essentially got cat-fished by a coworker. There had been some mutual attraction months before but I decided it wasn’t a good idea and told her we should just be friends. Then she made a fake online dating profile, used her knowledge of my likes/dislikes to attract me to this profile, carried on extensive communication pretending to be someone else, and then showed up to our date expecting me to suddenly fall head over heels in love with her.
She showed up at the date and I asked her what she was doing there, she replied “I think you know why I’m here” and I got in my car and left without saying anything. Eight years later and her cubicle is still 15 feet away from mine.”
7. Sounds a little unhinged
“So many adventures, so I’ll stick with the highlights. Dinner seemed to go all right, except that he drank most of a shared pitcher of margaritas by himself, then drank all the liquor I had at home. I was kind of irked, so we go searching for more.
The first place was closing up (it’s Sunday), so he goes up and bangs on the windows, loudly demanding that they sell us some beer and calling them assholes while I die of embarrassment. At the next place, after they served us, he casually said, “Oh yeah, I don’t have any money, so you’re going to have to get that.” (Not that I expected him to pay for my beer, but he expected me to pay for for his.)
In conversation, he mentioned that his favorite book was Ulysses and compared himself to Jack Kerouac. I asked him what kind of movies he liked, only for him to snottily retort that he watches “films.” He had me read a short story he wrote that, frankly, was pretty terrible, but when I offered polite criticism, he got angry and said I just didn’t understand. That was the problem with being a “natural writer,” he said. No one understands.
At one point during the evening he wanted to check on his dog. He said it wasn’t far, but it turned out to be a long drive to the middle of nowhere. Nothing was open, and I had to piss really bad. It was the most resentful roadside pee imaginable.
After he snapped at me about not understanding his writing, I said I was tired and he should go. He asked me for $3.00 for gas. I wanted him gone so much I actually gave it to him.
I later found out that he had a huge coke problem, and he told the mutual friend who set us up that we had sex that night but that I ghosted him after. The ghosting part was true, anyway.”
8. A whole series of them
“Mine is a series of dates that led to the weirdest one.
I was a student at a big state school and it was very possible to meet someone at a party and never see them again. I chatted with a woman a few times who was always interesting and engaging. She was a Christian and outspoken about her faith. I’m cool with that, but I’m not all that outspoken myself.
I asked her out to dinner and a movie after the second or third time of running into her and chatting and she said yes. I wanted to keep it traditional and do the whole date thing, so I cleaned up and picked her up to go to a restaurant and a movie. It went well. We hugged, said our goodbyes, and that was it.
We wound up going out again for a drink or something and things seemed to go okay a second time. It was sort of platonic, but we never had a conversation where we said that we were just going to be friends or something else. In either case, we were definitely going on dates.
So, I invited her out on my signature move- a canoe trip on a local river. It’s spring-fed, crystal-clear, and there are a number of deep springs with floating docks. It’s a great time. We both worked retail and had a day off in the middle of the week so that was the plan.
When she got in the truck, she was surprised to hear that she would be needing a bathing suit to go canoeing (?) and so we stopped at Target for her to buy one. I received specific instructions to stay in the truck while she shopped. No big deal.
When she got back to the truck, she let me know that she bought a two piece because all of the one piece bathing suits didn’t work. Awesome. Things are going swimmingly. Except she followed up with “it doesn’t matter. You will never see me in a bathing suit anyway.” That was weird, but okay.
The canoeing was fun. We swam. She swam in a T shirt. That was weird. But, overall, we had fun. On the way back to town, I asked if she wanted to order a pizza and watch a movie. She said she couldn’t, because she and her roommate had a policy that boys were not allowed over alone. Then she backed up and said that well, since these weren’t dates and we weren’t dating, that it would be okay for me to come over, but I had to leave by 9:00.
Hold up, I said. These are dates. She got all weird about how these weren’t dates, that we were just friends, and that she was not going to date. God would provide her with a husband on his accord. Right, I said. And these are dates. I’m not sure how you missed that.
She went on to talk about dating and marriage and then dropped that she knew I wasn’t the one because God told her that her husband was a baseball player. She knew that her husband was going to be a baseball player and she would consider going on a date with a baseball player, but it would be a stretch.
I rescinded my offer to watch a movie and order a pizza, and that I didn’t think I was interested in going down this road. Shortly after, she called my phone about a dozen times in a row because she had a flat tire and wanted me to come change it. I told her to check with the baseball team.
Epilogue- Some time later I was at a party, standing around a keg, and doing normal college student stuff when one bro asked another bro if he remembered to invite his girlfriend to the party. People in the know laughed and eventually the story came out that this random girl would come to every baseball practice and every baseball game by herself, stare, and pray. She’d try and interject herself in awkward and creepy ways and she would randomly show up wherever they were. This was pre-social media, so it had to have taken a lot of effort to make this happen.
So, there you go. Don’t not date crazy religious women who are betrothed to collegiate athletes.”
“The guy faked an Italian accent the entire time.
He was from Florida.”
“Once had a girl get up and go to the bathroom during a make-out session. Came back with her head shaved.
I asked why she did that, she told me her “head was too hot” and she “had been thinking about doing it for a while”
Made out for a little while longer until I could think of an excuse and got the hell out of there.”
11. Oh my
“I’ve got a weird one
met a girl at a bar
went back to her place
she did the whole whipped cream bikini thing
the whipped cream was spoiled
I muscle through sour whipped cream
30 minutes into fun time her daughter walks in on us that I didn’t even know was there or that she even had kids
another 15 minutes and her Aunt & Uncle walk in on us… yeah- wasn’t even her house but her Aunts.
She then breaks down in tears and starts telling me about being abused and her old heroin addiction.
then proceeded to tell me about her 2 other kids
I nope right the fuck out of there
a week or so later I see in the newspaper that she was in a car accident and died
surviving family members in the obituary included her current husband.”
12. Getting back out there
“First date after a broken engagement for me.
This girl kept telling me how much she wanted to go on a date with me off tinder. I was hesitant but she was persistent. Well, we got to the coffee shop and had some really nice conversation. Then she said she had some coworkers down the street that were at the Arcade Bar playing in a Mario Kart competition and if I would like to join in? Hell yes! We went down, got some beers and met the coworkers, super cool dudes.
She spent the rest of the night dodging around the bar trying to avoid them. Kept telling me how weird it was that they were here… uhh yeah but this was YOUR idea girl. Then she went to the bathroom and as she was getting up looked and me and said,
“can I bring my beer or are you going to drug me?”
Me “Uhh, what?”
“Are you going to drug me?”
“No, why the hell would I do that?”
“Ok.” Gets up to leave… “Actually, i’m going to bring my beer.”
Then when she gets back..
“My mom isn’t going to like YOU.”
Me “Uhh, ok why not?”
“You have me drinking on a thursday, I never do this. I can’t believe you made me.”
me “All of this was your idea, every single thing about it!”
Then when I walked her back to her car, she sprinted the last block to her car, got in and drove off. Then texted me telling me what a great time she had and if we could set up a time to meet again.
Edit: since people are enjoying this.
I had another tinder date with a second girl.
She invited me over to watch a movie. I came over and she was watching a movie with her roommate. They were already 25 minutes into the movie when I got there.
They didn’t want to talk while they watched the movie either.
So I sat awkwardly for two hours at a movie I didn’t know what was going on in. And neither of them would tell me what was happening.
Then movie ended and I got the hell out of there.”
13. Hi mom!
“Tinder date. Woke up to her mom knocking on her locked bedroom door and she made me hide under her bed while she had a full conversation with her mother.
She had her own apartment.”
“I was on an exchange program with a French school and matched with one of the girls in my class on tinder. We didn’t speak before but we made an appointment via messages to meet at her place to watch a movie. We then realized that I didn’t speak French at all and that she could only communicate with me because she put everything I wrote and everything she wanted to say into google translator but she didn’t speak a single word in English.
So we watched a Movie and tried not to be awkward. I wanted to make a move but not being able to speak with her made it very weird for me I don’t exactly know why. So I didn’t do anything and when the movie ended there was a long uncomfortable silence… that was probably the most awkward moment in my life.”
15. Just like a Seinfeld episode
“She talked about herself in the 3rd person the whole time. I didn’t realize until the date was almost over that she did not have a best friend with the same name as her.”