People Share The Worst Dating Experience They've Ever Had

Love is a beautiful thing but, also an insane, confusing, arduous life experience. Trying to find love can test anyone's most solid mental resolve. But we continue to try. And every date can lead to the best and most out there stories. At least there is that.

Redditor ItsMeMaple wanted to hear how off the rails other's love lives are to feel better about theirs by asking:

What was the worst dating experience you've had and why?

In the Family.


"On the very first date this woman decides to tell me she had an affair with her brother-in-law. Couldn't leave the bar fast enough."jzhoodie

Cue awkward conversation.....

"Went on a first date. Waited 60 minutes for food at the restaurant. Cue awkward conversation. Went to a movie and the movie jammed in the middle and we had to wait 20 minutes for them to fix it. Cue awkward conversation. On the way home, the car broke down and he insisted we couldn't call any of my brothers or sisters for a ride, so we walked 4 miles home. In the snow."

"We have been married for 37 years."4ninawells

Bye Girl Bye. 

"I got catfished but for some reason I felt too mean calling her out on it because she was a nice person, just not my type, and she had obviously used another woman's photos. Other than that she seemed very kind and I didn't want to hurt her feelings."

"So we still went to my place where eventually during a movie after some hints she finally just asked me, "Do you want to have sex now?" Again I felt bad, so I made up this lie about how I really wanted to, but I was a devout Christian and it was a war inside me. I got her a soda and we finished watching Captain America."

"At the end of it she asked me if I was gay and I said no, then she kinda rolled her eyes while we said goodbye."Kamehwik

Date ended there and then.

"I went on a date with a guy who not only felt that I was emasculating him because I won't let him pay for my meal and drinks. It was a first date and I believe in splitting the bill on the first date so that no one feels they owe the other. He kept demanding that I let him pay and I kept saying it's fine when he blurted out "just let me pay damn it. How the heck else am I gonna get lucky tonight?"

"Date ended there and then. I don't sleep with people of the first date either. It made my school year awkward though because we shared a lot of classes but for the most part I avoided him." Lark1987

Mr. Complex. 

"Mr Complex, ugh. It was seriously like he was a crappy movie stereotype come to life."

"He made a couple of snarky comments about me wearing heels on the date even though I wasn't. We were the same height (5'7") and I guess imaginary heels was the only way his mind could grapple with the concept. When we got to the restaurant, I opened my door to exit the vehicle and he began screaming at me for "making him look like less of a man" by not letting him open my door for me. A LOT of the dinner conversation was about how women don't appreciate "a male provider" "anymore".

"I was young and stupid so we ended up going back to his place and it was the only time I've actually had an "is it in?" moment. Afterward, he recalled that he's pleased many women before and they all said he was one of the best they'd ever had. Before I left, he let me know we were actually at his sister's house and she was in the bedroom next to us and to try not to wake her up leaving."

"What a sad dude. I hope he got therapy."Much_Difference

Just Twice.


"Not me but I was heavily involved in setting up the date. I set up a good friend, a girl with a guy I used to work with."

"Later that night after the date, she called me up and said "I think I'm related to him somehow." We go sleuthing on Facebook and text each other updates. And after an hour of talking to some distant relatives, we are dead certain that he's her nephew a couple of times removed."

"She calls me up sobbing saying they had already had sex twice after that first date. "Slash1909

Al Those Wings. 

"First night I stayed over at my partner's house. We both thought her family had gone away for the weekend and were somewhat vocal as a response. The morning proved us wrong when her mother congratulated us over breakfast she had specially prepared."

"She offered us tips and practical advice, also gave us a thumbs up. Best MIL ever. Mortifying at the time however."

"They had a large house, and her mother was keeping herself occupied in a wing we had no reason to enter, so we didn't know/expect her to be home."Lazy_Raccoon

All Cued Up. 

"Oh so many."

"Being an American immigrant of Russian Jewish decent and not married by 21, my mom naturally signed me up for a dating service. I have always been pretty open minded so whatever. Cue (or queue) a line of men (some in their 40s, some younger, most creepy) who were looking for anything resembling a woman that would lead to a green card."

"Personal favorite was a Dolph Lundgren lookalike who showed up in a suit, grabbed his heart Bill-and-Ted style, and proclaimed that I was the most gorgeous woman he had ever seen (spoiler, I am decidedly not) and he must marry me. Preferably by the 29th of March." Spectrum2081

It's All Aight!

"As someone who just got tinder thanks for making me laugh, feel self conscious about how i might end up here and how this could possibly happen to me." MeatBuu

"Hahah that's perfectly natural. I feel the same way every time I download Tinder, as do the friends I've spoken to about it."

"At the end of the day it's best to just be open minded with it. I've dated some incredible people through the app, as well as had some mind-blowing sex. I've also been through some horribly awkward dates and hookups, so you'll be right!"Justforfun_x

With the BF.


"Met a lovely girl over Tinder, we really hit it off and had a great conversation, decided to meet in person for coffee the next day."

"She showed up on time, looked just like her pictures - and brought her boyfriend."confettiicecream

The Good Start. 

"Dinner went pretty well, he was funny, sweet, so we decided to uber to a bar."

"On the way there we're holding hands and chatting, the guy immediately pulls his half erect member out and asks the uber driver to reroute to his home."

"The uber driver threatened to call the cops, kicked him out of the car, and drove me home free of charge."meghanarsenic

Not Ready... 

"I went on a first date with a guy. he was very educated and polite. he was friends of a friends and they set up us. they failed to mention that he just got out of a 5 year relationship and was not over her in the slightest. We went to a restaurant he frequently took his ex to, which i found out 10 minutes into the date. i would try to change the subject when he mentioned her but it was obvious he needed someone to vent too. so i spent the date letting him get out his thoughts/emotions about his ex. he wasn't a bad guy, he just wasn't in a position to be dating anyone."tinydancerxo

3 Bottles In.....

"She ordered three bottles of wine at dinner. I had maybe three glasses total. Which means she had 9 glasses on her own. When she tried to order a 4th one the waiter cut her off. She caused a scene and got us kicked out of the restaurant. I called her an Uber and while we were waiting she pissed herself in the parking lot. Basically poured her into the back seat of her Uber and went home. She texts the next day- "hey sorry I missed our date last night, I must have taken a nap and slept through it. Reschedule?""

"For context "mean bar" is a bar my ex works at. Blackout had originally suggested we meet there for drinks and I had to explain that she works there and is kinda crazy and I probably shouldn't take a date there. She knew that's what I called the place. When I first said I'll get back to you I was really contemplating a second chance because she's smoking hot. But ultimately my big head prevailed over my little head."Reddit

A Knight's Tale.


"Sophomore year of college, my roommate and I decided to double date. It was the first date for both of us and we invited the guys to our apartment to watch A Knight's Tale. My date got drunk within 20 minutes and spent most of the movie face down in my lap mumbling "It's just so anachronistic!" while my roommate and her date cuddled and laughed at me."HugOWar

'what the hell, why not'

"My only blind date..."

"My college roommate had a date, asked me if I'd come along and take out his date's roommate."

"I thought 'what the hell, why not'

"We arrive at their place to pick them up."

"My date comes out, she's cute. She looks at me and just says, "Oh hell no". She goes somewhere else."

"I drown my sorrows in pitchers of margaritas...find out they have a 2 pitcher per person limit, and we're at 6 pitchers already."

"I call a buddy to join us. Buddy arrives, sits across from me. Order 2 more pitchers of margaritas."

"Buddy tells me he had plans with a girl he'd been dating for a bit, but the plans had just fallen through, so let's get f'd up."

"Three minutes later, the girl he had plans with arrives on a date with another dude...sits at the table right next to us."

"We call another buddy to join, so we can get 2 more pitchers of margaritas."

"In retrospect, we should have gone home after the second pitcher of margaritas."AMMJ

The Widower. 

"Didn't quite get to the dating part. My best friend was a guy and his girlfriend didn't like me hanging out with him. She decided she wanted to set me up on a date to get me out of her hair. My best friend asks me to please do this to get her off his back. Apparently the guy she wanted to set me up with was her coworker's brother. He was a young widower and a solid guy. I reluctantly agreed and she gave him my number. This guy called me and we talked. He told me that he was a widower. We talked about his job."

"He didn't ask me out. Three more conversations over the phone and he still didn't ask me out. I finally told him if he wanted to go out on a date it would have to be soon as I was leaving on a lengthy trip soon. He said he was waiting. I asked him what was he waiting for? And his reply was.... the funeral. His wife's funeral. You could have knocked me over with a feather. I noped out of that asap and told him he should wait a while to date. Was sooo mad at my best friend and told him his girlfriend could screw off."Roo514

"I don't believe in dental hygiene"

"They walked into the restaurant immediately said "I don't believe in dental hygiene". I believed them as they had black teeth and gums that I could smell from several feet away."

"I could not tell if it was a joke, or some sort of experiment, but it was hard to focus on much else. It was easily the most disgusting mouth I've ever seen."Seigest

Hissy Fits....

"Probably any of the dates with my abusive ex when she would throw a public tantrum to 'test' me."

"For example, the last time we went out together before I managed my escape we were going to the zoo. She wants to cross the road, I ask why and point out we can't get to the zoo from that side, she immediately goes into a screaming hissy fit, shouting, tears, the whole works, right there in the middle of the street in a very busy city."

"I was pretty used to it and done with the whole thing by this point in our relationship, previously I would have been desperately trying to comfort her but this time after she wouldn't tell me what was wrong I just walked away. Tears dry up, comes running after me, finally explains there's a shop across the road she wants to visit. 10 years later I can still feel the exasperation with how bloody stupid the whole episode was."Aypreltwenny

A Goat?


"I went on a tinder date that ended in me leaving because his friends showed up at his place with a stolen goat. They wanted to kill it and try to get in touch with the spirit world. I wish I was kidding." LN3132

One second thought, perhaps we'd be happier alone than dealing with some of these stories.

When you gotta go, you go.

That should be a mantra for getting rid of the toxic people in our lives.

Not every relationship is meant to last forever.

Some people don't know how to be friends.

They are awfully good at pretending though.

Be vigilant of the signs and red flags.

Toxic people are crafty.

And once you're free, never look back.

Keep reading...Show less
Decorative wedding sign that reads, "Eat, Drink, and Be Married"
Photo by Ben Rosett on Unsplash

There's nothing quite like the drama that can arise at a wedding or in the days leading up to it.

But the moment people don't necessarily think about is the moment when the audience can choose to object if they so choose, and surprisingly, some people take advantage of this opportunity. It often doesn't go well.

Keep reading...Show less
Person holding up multiple $100 U.S. dollar bills
Photo by Jp Valery on Unsplash

Financially speaking, most of us could benefit greatly from having extra money each month.

But where someone might assume that the extra money would just be wasted, most people would apply these funds to very practical purposes and expenditures.

Keep reading...Show less
Paper ripping in two
Kelly Sikkema/Unsplash

When love is on the rocks and there's no salvaging a relationship, it's better for a couple to call it splits.

Sometimes the reason for a breakup is obvious.

Other times, it's more complicated.

But the people involved going their separate ways is better than staying in an unhealthy relationship.

Keep reading...Show less