Dating is one of those few things that causes seemingly universal anxiety. As anyone who hasn’t yet found “the one” can attest, one encounters a lot of weird people and even weirder situations while driving blindly down the road to finding a soul mate. If this topic sounds relatable, keep reading below about some of the worst dating experiences our fellow internet-goers have ever experienced! And it can’t hurt to take these stories as a lesson in what not to do when out on the next date…
24. To Each Their Own
Girl and I went out for our…second? or maybe third? date. We were going to see a movie with a bunch of her friends, and then hang out after at a Dairy Queen or something. Cool. Well, she was only interested in me until her friends showed up…she spent the time waiting for them just whining about her coworkers, then when they showed up she basically ignored me the rest of the evening. I introduced myself and chatted with a couple of her friends while she sat with the rest at the next table over.
Apparently she thought the date went really well. She leaned in for a kiss when I was saying goodbye, but I wasn’t feeling it at all so I went for the awkward hug instead. Later told her I wasn’t feeling any chemistry between us and she seemed a bit confused why.
23. Two’s Company, Four’s a Crowd
I asked a girl on a date. She said sure. We agreed on the details, I’ll pick her up at 4 pm, then we can do go-karts at the local speedway. Unbeknownst to me, she invited 2 of her friends. Since I was a spineless 19-year-old at the time, I couldn’t assert myself to tell her friend not to smoke in my car, and also that I don’t want to pay for their go-karting. Ended up paying around $300 for all 4 of us to go race, but my “date” had to stop at the 3rd lap because she crashed with some stranger.
22. Checking Every Box on the Nightmare List
I met a girl.
A total 10 to me in every way. Great potential from the get go…I wanted to have an amazing first date because I’ve always tried to make them memorable (after all, they’ll be talked about forever if you end up together).
I wanted to keep it simple, nothing too crazy, but she liked coffee.
So my plan was basically to take her downtown and we would walk in the beautiful snowfall from coffee shop to coffee shop trying them all until we agreed on the best one!
So I go to pick her up. I arrive at her apartment, and I pull up to the front door. She’s not there.
I message her and she says she doesn’t see my car. We have a back and forth before I zoom out on my map and realize there is an identical apartment across the street, mirror image. So her screenshot she had sent me looked the same but was backwards.
She hops in and we start to chat, and I feel my pocket for my wallet and realize it’s not on my person.
[X] Forgot wallet
Drive 20 minutes home and search. Not there.
[X] Lost Wallet
Drive to parents’ house (10 min) because I might have left it there, my parents get to meet a girl I haven’t even taken on a first date yet. Left. No wallet.
[X] Awkward Parental Encounter
Realize I might have left it at the house I was building (I work in construction). Drive 10 min. It’s there! And I get to impress her with my craftsmanship on the house.
Finally a plus!
[X] Over An Hour Late For Date
Head downtown. All the coffee shops are now closed.
[X] Plan Blown.
Time to improvise, I’ll take her to a bar or burger joint downtown. Get in there, we had both eaten dinner, neither are hungry…we order a side of fries.
[X] Awkwardly Small Meal.
She’s a month away from 21. We just have waters.
[X] Awkward Drink Situation
Meal cost $4.
[X] I Feel Cheap
I take her to the fanciest ice cream place in town to make up for all of this. It too is closed.
Decide to just say screw it. We need ice cream so we walk into the grocery store to get some. She runs into her roommate who wonders how the date is going. I walk off to get supplies and this girl explains how bad it is so far. I get ice cream!!
[X] Weird Roommate Encounter.
Need plastic spoons, I can’t mess that up, right?
grabs box of plastic forks
So we drive out, park in a parking lot and eat this ice cream with forks because the whole date has gone down the drain anyway. We chat and chat and forget about the ice cream…..
….until I lift up the box and it’s melted all over the console of the vehicle.
[X] Melted Ice Cream All Over The Car.
So we clean it up, finish chatting, and I drop her off. No second date surely.
[X] Nightmare Over.
Until she texts me “that was the worst first date I’ve ever been on…
…but I loved every second of it! When can we hang out again?”
I was over the moon!
And then my car ran out of gas a block from her place so she picked me up, drove me to a gas station, I bought and filled up a gas can and then returned home.
[X] One Last F-Up
So despite all that, the two of us are together still and in a few months I’ll be proposing. So I guess it turned out alright!
21. Dining and Diving
The girl claimed that she was going to pay for her half. When the check comes, she asks to use the bathroom. 10 (awkward) minutes go by and right when I’m about to text her she zooms out of the restaurant, leaving me with the check. Plot Twist: I got to have sex with her friend, so we’re even.
20. My Mistake
I was on a first date with a girl I also worked with. We’d been flirting for weeks and had wonderful chemistry. Our date was great and had a life of its own. She drove. At the end of the 6-hour long date, we were sitting in her parked car in front of my house, continuing the captivating conversation. We had a work meeting the next morning, so when it came time for me to go, I started to exit the car and said “See you tomorrow.” She sheepishly said, “I can’t wait that long.” Without thinking, I replied, “Well, you’re gonna have to,” and slammed the car door.
I didn’t realize what she meant, or how what I said came across, for some time, like the next day.
19. Take a Hike!
I took a girl hiking, and to cut to the point, we took longer than expected. She was apparently afraid of the dark and was running around and telling me that we were going to die. Not the best experience. I basically had to push her along the trail, taking about an hour or two before we finally got back to my car, where she promptly thanked me for “such a good time.” Yeah.
18. A Portrait of the Artist as a Young Woman
I took this artsy fartsy girl to a theater for a play. Cool, whatever. Afterwards, we’re walking back to my car and everything is going normal. Small talk and all. She suddenly breaks down into tears and cries about missing her ex. Darn. I guess we’re not getting Chinese food anymore. I take her home. She lives in boonie-ville. Foggy as heck at night. I drop her off at home, thinking I’m never taking her on a date again. Head back home. Phone loses signal because boonie-ville. I run a red light because of the thick fog and the GPS starts going nuts. I hit another car and total my car.
0/10, would not go out again with an artsy girl who was secretly still stuck on her ex at the cost of an entire car.
17. Well That’s Unfortunate
My worst experience is that I’ve never been on a date.
16. Umm, Alright Then…
A friend ended up telling me about her friend’s “crazy night,” was pissed, and confronted me. Said her “friend” can’t be the only one to have fun and she wanted to get even. She ended up coming to my apartment and had a one night stand with me. Was still pissed at her for what she did so broke contact with her despite her suddenly catching feelings for me. I kept having sex with her friend until a week later when I found out she had a boyfriend.
15. Biting the Nail
l bit straight into a bite of food, forgetting how hard it was, and almost cracked my molar.
14. No Necking for This Therapist
So, I’ve read a lot about neck beards. I’ve never seen an actual neck beard in person, however. Then I went on a Bumble date with this physical therapist.
The beard growing out of his neck, alone, killed any desire that I had. I get it now, everyone.
13. Even Pleather Can’t Save You From This Threat
Getting bit by her on my arm so hard that it left mild teeth marks and a massive bruise, even through my thick pleather jacket.
12. Think of This as a Learning Experience
I asked a girl in my class out on a date a few years ago, we had all the details set in stone, and I showed up to find out she invited the 30 other people from the class. I had to sit through an hour and a half of the “class lunch,” which she gave me credit for organizing, and pretend that I didn’t think it was gonna be a date the whole time. Ouch.
11. Horrible Is Relative?
Not everyone has the same experience with some of these stories. In the last one, he asked for a date and was expecting a date. Girl, unaware of his intentions, decided to bring 30 people, meaning HIS date was ruined. To her, it could have been an awesome time!
10. From Bad to Worse
Chick asked me to go to the movies.
Right before I leave my house, she tells me that three of her friends were also coming.
I get there and she tells me to just sneak into the theater that they snuck into.
We all get kicked out.
9. Opposites Don’t Always Attract!
With some girl I was talking to online who agreed to meet in a pub but then only ordered lemonade after lemonade whilst me (as the heavy drinker that I am) was just downing pint after pint amidst her cringeworthy attempts at starting a conversation that went absolutely nowhere.
Clearly neither of us were comfortable, but there didn’t seem to be a socially acceptable way of ending it. When we walked around an art gallery in Camden that had a bar, I disappeared off to get a drink—and she didn’t bother trying to find me afterwards. That ended it good enough, and it strangely turned into a pretty awesome night drinking with random people.
8. Worst Case, Bar None
I met a guy online. Can’t remember which site, but he scheduled the date at a bar—not even a restaurant, a BAR. A bar that didn’t even serve food. He was apparently a recovering alcoholic so he only ordered Cranberry juice, but he failed to tell me that until after I had already ordered a glass of wine.
Why on EARTH would you invite someone to a BAR if you’re an addict? The entire thing was so bizarre to me, and on top of it he turned out to be a complete jerk.
He ended up leaving and wanted to walk me back to the metro and I basically said “no thanks, I’ll stay here for a bit.” He was shocked and offended. I don’t fully know what he was thinking, but he finally left. When he left, the bartender immediately came over and was like, “holy cow, that guy was a DOUCHE!”
He took care of my tab and gave me another drink on the house. So there was at least a silver lining.
7. This Can’t Go Wrong in Any Way…
“I’m a recovering gambling addict, want to go to Vegas with me?”
6. A Word to the Wise
You always gotta watch out for people trying to use you. Once that happens, you tell her to bugger off. If she knows it is a date, games shouldn’t fly unless she is just using you.
5. Unmasking the Facade
It was less of a date and more of a hook up. Very handsome dude. I made my intentions clear and asked him what he was interested in. “Firefighting, sex, and fighting.” Yeah, tough guy, let’s meet for drinks and go back to your place! Have drinks, going well. Go back to his place and have more drinks, still going well. Start getting down to business and, when we’re both nearly completely undressed, he pulls away. Quickly dress and run out the door with a pat on his head while he cries about his ex-girlfriend. He was not ready for a hook up.
4. It Must Suck to Be You
My worst date? All of them.
3. Who Was This One Bad For, You or Them?
I threw up onto their shoes and then continued to drink more.
2. Red Flags
So I met this girl on Tinder. She seemed nice enough at the time and I was sorta new to this whole Tinder thing so I must admit the red flags slipped right past me.
She rocked up half drunk in a torn dress. Now I’m not one to judge people’s lifestyles and I was starving, so for some reason I decided to press on with the date.
I spent the next three hours listening to her moan about her current boyfriend and how he was such a controlling guy because he wouldn’t let her go out on one-on-one “catch ups” with guys at bars.
When I finally came to my senses and told her that I didn’t particularly want to be on a date with a girl who was seeing someone, she threw her drink at me and accused me of assaulting her. Thankfully, the bartender had been watching the entire series of events and took my side on it.
She got thrown out, and I didn’t go on another Tinder date for the next few months.
1. Taking the Term “Blind Date” a Little Too Far
Not sure this counts since the date didn’t actually happen, but I was set up on a blind date. We planned to meet at a restaurant.
I got there first and since it was a nice day out, I sat down on a bench outside the restaurant. He ended up calling me on his way over and I told him where I was sitting. He was still on the phone when he started walking up to the building. He took one look at me, hung up the phone, and walked back to his car.
I tried to call him back, thinking something must have happened, and he didn’t answer. No more answers to calls or texts afterward.
Bonus: Cheaters Never Prosper
I knew my ex-wife was cheating but didn’t tell her that I knew. Took her out for a dinner date and I casually asked questions about who she had been spending time with while I was at sea, she barely worked so she had to spend her time doing something. She failed to mention the guy that had been staying at my house for nearly 2 months, the guy she had to call the cops on just to get to leave because I was coming home in 2 days…soooo I slid her a copy of the police report that was filed for the incident and watched as she crumbled over the fact she had been caught, and I didn’t have to say a word.