People Share The Most Cringeworthy Dates They've Ever Been On
With dating apps, it's easy to be a couple of steps removed from the person you're planning on meeting later. You don't know their mannerisms, what they're like, if your quirks match up. But boy oh boy, you're going to find out.
Here were some of those stories.
This Is How You Know It's Love
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.
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.
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, hes 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.
Two Kinds Of Weird
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!
People Will Exploit You
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.
Eight Awkward Years
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.
$3 Is No Cost For A Lifetime Without You
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.
Attend The Tale
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.