Hopeless Romantics Share The Worst Date They've Ever Been On

From hitting on another woman on a first date, to forcefully trying to kiss the person, people recount the worst dates they've ever been on.

[Source can be found at the end of the article]

I started dating a girl who was 20 years old with two kids — a 3-year-old and a 6-months-old, both girls. I know, red flag central. Both girls were adorable and really sweet.

She couldn't afford a babysitter so our dates consisted of me going over to her place, hanging out and helping with the babies. Honestly it sounds terrible but wasn't that bad.

One day she asks me if I can babysit so she can run some errand. She said she'd be gone 30 minutes and the babies would be napping. Then we could have a date night kind of thing. So this is the date.

I go over there, we say our hellos and she heads to run errands. Well she ends up not coming back for 4 hours. During this time the babies woke up. I got them changed, fed, dressed and entertained them. 

Finally she comes back and we get into it. She admits that she met up with the baby daddy.

She literally slept with the baby daddy while I was watching her kids.


It was a blind date. We met up at a coffee shop close to our university. He was very high, and it was hard to get a conversation going. He just kept telling me I was as beautiful as the brick wall we were sitting next to, and that my skin looked soft enough to be made into a nice robe. The date lasted maximum 15 minutes.


A friend set me up with a girl he knew. She was cute, funny, smart, everything you hope for in a blind first date. After spending a good part of the day with her, we end up at this frozen yogurt spot. We talk for a bit and she mentions how much fun she had today. Then she says how much her boyfriend would like this spot and that we should all hang out next week. Never asked that friend to set me up ever again.


He was more than three hours late, and was texting me telling me that he was 20 minutes away for two of those hours. As soon as he arrived he tried to tell me to leave the part of the venue/dive bar I'd already paid in to so we could go where he wanted. He tried to start a fight with a friend I'd happened to run into, and called my aunt (who'd talked me into going out with him in the first place) horrible names. I just walked away from him after that last one, and we never spoke again. 

I waited so long because I liked the bands that were playing. I wouldn't have stayed if I was sitting around doing nothing. He got there just before the last band finished, but I'd had about enough of him by then because he'd been telling me that he was on the train in the same place for two hours. We don't live out in the middle of nowhere and he could have easily gotten a bus or tram the rest of the way in that time if there was a problem with the train. He never gave me a proper excuse but I didn't really care at that point.


I dabbled into some online dating a while back when I was single. This one guy refused to meet me inside the coffee shop. So I decided "I'll meet him outside." We walked around the little mall for a bit, chatting about our jobs and such and what he wanted to do after our little "date." He ends up driving me home and showed me this furby that he claims he likes to punch when he's mad and busts out the "So can I get into your pants or nah?"

Not really "worse" but awkward for sure. 


Several dates in and its starting to get fairly serious with this girl. We had been spending weekends at each others places and stuff. 

So one day we are on a date at a restaurant and she goes to the bathroom, comes back, and it's obvious that she had been texting. Her phone was in her hand and she turned her body a bit to talk to the server. As she turns I can see her phone a bit and she had been sending nudes. From the bathroom and on our date. The name at the top of the text is her ex. I excused myself to hit the bathroom but instead just left her stranded with the bill. This was before Uber, and taxis are not cheap in Jacksonville.


Online dating in your 40s sucks. I met this guy online (it was not Tinder) and he kept bugging me to take me out to dinner. I finally agreed and he said he wanted to take me "somewhere nice." Now I don't know about any of you, but when I hear "somewhere nice," to me that involves wait staff and tablecloths. We agreed to meet in a well-lit grocery store parking lot and ride to the restaurant in his car. It's cool out so I put on a dress and tights and high heeled boots and go to meet him in the parking lot of the strip mall. He pulls up in a Mercedes and I wonder if I'm dressed well enough for wherever we're going. We do the greetings and I get in his car and he drives across the parking lot ... to the Taco Bell drive-thru. I am not joking. I text my teenage daughter and she tells me that things like that only happen in the movies. Needless to say, there was no second date.


In college, I went ice skating with this engineering student who's never done it before. I don't know many tricks but I can ice skate and break freely and he was hanging on the handle the whole time. I tried to convince him to let go otherwise he won't learn and even hold his hand but he was rather stubborn. He tells me during the session how he was reading the physics of ice skating the night before but realizes it isn't helping him here. We go to a cafe after and he starts saying how ice skating is so stupid unlike chess that has a specific purpose and then shunning me for other likes of mine.


First date with this girl I met from OkCupid. It was going fairly well until she got super drunk and started telling me about all the guys she slept with. That turned me off almost instantly. Im not much of a drinker; I only had 1 beer.

I try to make my way back to my car and she is begging me to take her back to her place. Eventually starts offering me money. Finally says Ive never had so much trouble getting a guy to come over before.

Pretty sure I dodged some type of bullet there.


I believe it was the very first date for me. It was with a classmate too so it was extra embarrassing. We were in very early teens, still riding bikes everywhere. So we went for a bike ride, went to visit one other classmate for a bit, then went to the school yard and texted with each other on our phones. It was so awkward. I broke up with him next morning just before first class, via text message, when he was standing like 2 steps away from me.


I was going through a rough break up so my aunt set me up with the son of one of her friends. The first date actually went decent, but on the second date I was absolutely sure there was no chemistry. I was trying to figure out how to politely tell him I wasn't interested, but on the way out I actually forgot where I parked my car and had to spend a lot of time looking. I think he decided I was way too stupid and didn't call me again. So hey, winning.


This was my first and last Tinder date. We went to the cinema and before the movie started, he was the loudest, longest and most animated talker I had ever met. People were staring. After that we went for drinks and he went in for a kiss very quickly. I sort of froze out of embarrassment and it just happened. He literally put his lips over my lips and started sucking. It was so moist. His saliva was all over the bottom half of my face and I had to excuse myself and go to the bathroom to wash it off. After that date he wouldn't stop messaging me. His texts were so long that I had to scroll. Their content was mostly him begging me to give him a chance and that we 'had something.' I had to block him on everything.


When I was 16, I thought this girl was really cute. We would chat on MSN but it was all just friendly stuff. Eventually I started dropping hints that I liked her and it led to us arranging to meet up and hang out. She flat out admitted to liking me too so I knew I wasn't getting the wrong idea.

We met up in town, not to go anywhere in particular just hang out. She had decided to bring her friend and we then met up with another and the three of them wouldn't stop talking to each other so it was just really awkward and boring. I texted my friend saying how awful it was and I needed to find an excuse to leave, or at least I thought I had. I had actually sent it to the girl I was there with and she showed her friends. As I realised what was happening I made up some excuse and just hurried off. Awful.


When I was 18-20, I went on a string of dates so awful that my friends requested I start a blog about it (I didnt). There was one guy who asked me out, and he took the train four hours to meet up in my hometown at a pizza place. He showed up in tattered jeans with patches made from towel swatches sewn on, and an equally tattered jacket. He was in one of my classes, so I knew this wasnt his regular standard of attire, but I decided to roll with it. So were sitting, eating our pizza, and he puts on a clown nose out of nowhere and keeps eating. I ask him if theres an explanation to that, and he said he was just trying out his new nose. Okay... Then he started jazz scatting like hes Ella Fitzgerald. For two hours, just jamming to himself in a pizza place with a clown nose. 

I didnt want to leave because I was his ride back to the station and he had come so far to see me. Eventually, I drive him back to the train station. He doesnt get out of my car. I ask him why, he says Im thinking. Then he leans in like hes going to kiss me, rubs his face on mine like a cat, licks my face and leaves. Of all of my bad dates, none have ever left me more confused than that one.


He took me to go see a psychic, who proceeded to tell him that we wouldn't last as a couple and would end up splitting up. On the 2 hour drive home he cried and said he didn't see the point in dating if we weren't going to end up in a proper relationship. I just wanted to get out of there, but to make matters worse, when he pulled up outside my house he locked me in his van and wouldn't let me out. Oh and then he would watch me from his van for about 3 weeks afterwards and ring my phone continuously so I couldn't use it.


I met a girl off a dating app who I thought was cute, funny, and all that nonsense. I was in a different city, visiting to get a tattoo done. This was on my last day there: so we decided to meet up. We had a few drinks. It was edging close to my departure cut off point to get to the airport when I decided to risk it and we took all our sexual tension out on one another in a clothing department change room.

I ended up missing my flight due to the Metro system having a complete and utter breakdown. She offers to put me up for the next couple of days to get the cheapest and earliest flight out. That's when things got intense.

Finally I get back home and resume my overnight shifts at a fast food place. Every time I finished my shift, I'd notice a 20 long winded text messages on my phone. I'd go home and sleep, and wake up to the same. If I didn't answer them promptly enough, she'd send passive aggressive texts.

It ended up being way too much for me too handle, so I ghosted her. Only for her to find my Instagram account (and over the period of a week before I got any form of notification) and sent me countless abusive texts, ending it off with "this is ridiculous! well, I'm done antogonising you, bye." And that was that.


I met this guy online years ago. We chatted on the phone for a few weeks and he seemed great: solid family, great job, similar interests. So I agreed to go on a date: ice skating, see a movie and grab a drink afterwards. Sounds like fun!

So the day comes and we hit it off. He's handsome and witty, holding my hand while we're skating and having a great time... until I hit a rut in the ice and fall. And that's when the pain hit. It took me 20 minutes to walk a half block to our car and then I couldn't sit because the pain was so bad. I told him I think I should go to the ER to check it and his response: "Cant it wait? I really want to see this movie."

By now, I was in tears cause it hurt so bad and he was still giving me a hard time. Finally he agreed to take me to ER. We pull up to the hospital and he turns to me and says, "You can handle this yourself right, Im pretty tired." By this point I didn't care and said sure. Turns out I had fractured my tailbone landing on the ice.

Never heard from him again... until almost 10 years later. I'm now married with a 3-year-old and I sign my daughter up for a parent/tot gymnastics class and guess who is one of the dads!? He kept looking at me, I would glare back but he never said anything then either. Time was not good to his looks so I think I got the last laugh!


I went on a date while I was in college. We went to a breakfast restaurant in the evening. Strike one was when I got out of the passenger side of his car and closed my door, walked around to the other side of the car and saw him already walking into the restaurant. (????) And then later when the waitress brought us our food, he took the eggs off of my plate and put them onto his. Like as soon as the plate had hit the table in front of me. I hadn't even picked up my fork yet. When I asked why he was doing that he responded: "I need them for gains."


Im a big, strong guy but a scaredy cat when it comes to horror films and such. However, this extremely attractive girl wanted to go see a horror movie as our first date and I was willing to act tough... except I couldnt. I tried but I just cant handle jump scares! Gore, blood and disgusting stuff Im fine with, but dont you try to scare me. Long story short, a jump scare happened and I spilled a good portion of my cola on her white shirt.

For a moment I hoped that I would just apologize and a few weeks later we would just laugh about it and have it as our cute story. Well, she had a different opinion. She changed seats, finished the movie, let me drive her home without saying a word and didnt respond to my texts anymore.

Needless to say I am still amused by this story to this day and so are my friends.


I arranged to go out on a date with a guy. He asked where I wanted to go. I said that it would be nice to go somewhere where we could have a game of pool. I should perhaps have specified a pub with a pool table, because the place he took me to was a pool hall, and it was almost totally deserted. He was nervous, and kept doing awkward things when he either hit or missed a shot. When he eventually won a game, he pretended to hump his pool cue and did that butt slapping gesture. It was so terribly uncomfortable, I just wanted to get out of there.


I went on a date with a guy who was SO NERVOUS. He picked me up in his car and was shaking as he was driving. I thought "That's a bit odd, but whatever." We get to a coffee shop downtown, and he chooses a very very over-the-top flowery coffeeshop. The walls, furniture and wall hangings were just all floral print. I wasn't into the place. But whatever. We had coffee together but he was shaking and sweating badly. The bill came and he reached for his wallet but he forgot it in his car because he was SO nervous. I had no problems paying so I paid the bill and he kept apologizing. The whole time leaving the coffee shop and the ride back to my house he kept saying "I'm so sorry," looking down and looked so sad. He never stopped apologizing. He was so embarrassed but I was just annoyed. Like - these things happen. Move on, no problem. He was the worst date I've ever had. There wasn't a second date.


He had cat-fished me with his pictures, and I just wanted to get out of there as soon as possible.

I begged him to split the cheque, because I had no intention of seeing him again. He wanted to pay for the whole dinner, and even after so much insisting he wouldn't split, so I gave up and let him pay.

And after paying for the meal, his body language changed from creepy to super creepy. I think he literally thought he had 'bought' me by paying for my meal.

As we went downstairs, he ran his fingers super low through my crop top, I was instantly taken aback but didn't want to make an issue. Then came the time to say goodbye. He was adamant that he would drop me home because Delhi is an unsafe city for girls to go home alone in a taxi at night, which wasn't chivalry on his part but just an excuse so that he could kiss me in the backseat.

I agreed apprehensively. In the taxi, he was literally forcing himself on me. He showed me his tongue, started making faces like he wanted to passionately kiss me, all this while his hands were trying to explore over my jeans. I made an excuse of getting motion sickness and shifted to the front seat of the taxi.

This guy, apparently changed his plans of dropping me home and asked to be dropped off mid way. (Thank God !!)


We were teenagers who worked together. He asked me out on a date to the movies and I said yes. I asked him if I should take my parent's car (reliable) or his car. He didn't care either way, so we went in his car. He was running late and we arrived about 15-20 minutes after the movie had started. When it was time to pay, he said he had forgotten his wallet, so I paid for for both of us. He said he felt super embarrassed and would pay me back (never did). The movie was bad- one of the Saw sequels we had no interest in watching. Afterwards we walked to his car but it wouldn't start. I was starting to get worried because my parents thought I was out with a friend (I wasn't allowed to date yet) and it was close to my curfew. He said his cousin worked at the theatre and would help jumpstart his car after he got off work in a half hour or so. So we waited and had awkward conversation. His cousin got off work later than we expected, and jumpstarting the car didn't work. So my date called his parents to come pick us up, and I was finally able to go home an hour or two past my curfew. Thankfully, my parents weren't too upset. I honestly thought the whole ordeal was pretty funny and was hoping for a second date to make up for it. Later, he posted on his Facebook about crushing on some angel girl and I initially thought it was about me, but it turned out to be someone else and I cried a lot about it. He avoided me at work.

After some time, we became really great friends. Totally platonic. He later told me that after the date, he was so mortified that he couldn't be around me or look me in the eye (couldn't pay me back though!) Our friendship lasted a few years and then I don't know what happened. Life, I guess.


A guy on a dating app invited me on a breakfast date on Saturday. When I arrived to the meeting point, I realized he meant a breakfast date at his place while I thought we were talking about having breakfast at a cafe (it was our first date ever). Also, it turned out the meeting point was basically in front of his house. The guy planned the logistics of the date pretty well. He was obviously not going to waste his time on nothing. So, when I realized that he basically tricked me (he never made it clear that the date was supposed to take place at his apartment) I got annoyed and told him there was no chance Id go to his place on the first date when I just met him and that there were two options: either we have breakfast at a cafe or Im leaving. He tried to talk me into it using all his charm: Listen Ive already made pancakes for us! What bad can possible happen? You can leave any moment of you dont like something! We are not going to do anything you don't want to, I swear! Well unless you want to. Im an experienced lover! Dont be such a baby! Many girls have been to my place and none of them have regretted coming with me! Dont miss this opportunity! 

I was laughing in his face while listening to this absurd monologue and when he finished it, I said I was done with this and tried to walk away. He then grabbed my face and tried to forcefully kiss me. I got really furious, pushed his face away, told him he was a creep and walked back to the metro station (we were still just 50 meters away from it since his house was basically in front of the metro entrance). 


I went on a date with my friend's older brother. We'd been talking for a week, had met on a night out. He seemed nice, knew a lot about food and seemed pretty cool. I have pretty major intolerances to wheat and dairy (was in and out of hospital for a year during my a-levels) which I'd made clear to him the severity of. Flash forward to the date where he takes me to a small restaurant (alarm bells are already flashing). I ask if they have an allergen menu, they say they don't and that the only 100% safe meal has been sold out. At this point, my date does absolutely nothing, he can see I'm majorly panicking and tells me to calm down and he then proceeds to order. I don't eat anything and we split the bill after.

We then move onto drinks, earlier on he's said he's not a fan of whisky, I order a double Jack and Coke and he does the same, this just irks me for some reason, unsure why. When we proceed to sit down he tells me about his job (he works at an opticians) at which point I look back around and see he has a glasses wipe out. Without asking he takes off my glasses and cleans them for me, telling me it was bothering him. At this point I am done and try to wrap up the night as quickly as possible. I don't see him again.


It was kind of a group date thing with a couple of my friends and guys we had a collective crush on. We went canoeing which I thought was awesome. Except, the guy I liked didn't show and the guy I ultimately got paired with for this canoe adventure is not into me and I'm not into him. I say screw it, we can be friends, we can still have fun today! But he was not happy. And he made it pretty clear he wasn't happy when we got down the river a good way and he just stopped paddling. The water was pretty shallow at this point and I needed all the help I could get to keep us off the rocks. But he just put his paddle down and started drinking. When I asked if he could help get us down the river with everyone else he said, "no, but you can blow me if you want." I got out the canoe, tipped the canoe where he fell out, his beers fell, and his phone started floating down the river. I got back in, threw his paddle at him, and started paddling myself down the river alone. 

I finally caught up to the rest of the group and when they asked where the guy I was with was, I just acted like I had no clue what they were talking about. Everyone was so drunk they legitimately couldn't remember if he went canoeing or not. That lasted about an hour until one of his friends went down the river again to retrieve him. He was sleeping on a beach, burnt to a crisp, with a ruined phone. I left before they got back from the river and promptly reevaluated my "friends" and the group I hung with. 


First date with a guy from a dating app earlier this year. His friend is doing an improv show downtown. We meet up at the cafe/bar below the theater an hour before the show to get a drink and chat first. I show up (6:00pm) and hes already 4 drinks in. Not a great start. We chat for a bit and its going okay. His friend comes down a few minutes before the show to say hello. His friend is a woman, thats fine, I have friends of the opposite sex, no problem there. Shes about 10 years younger than he is though. Then he starts hitting on her, hard. Shes looking nervously at me like "What's going on" but he keeps going. She leaves to go backstage and we head to our seats, and he brings a bottle of wine with him.

The improv show is pretty funny, I enjoy it and have a pretty good time. He drinks most of the wine. After the show its clear hes pretty drunk but Im starving and ask if we can get food. Were downtown, plenty of options. I want to go to the burger place next door but he suggests a fancy restaurant nearby, so I say fine. We go in and sit at the bar since we dont have reservations. He immediately orders a drink (sour beer...) and an appetizer for me without asking. Okay... Im not a huge fan of sour beer, but the appetizer is great. He doesnt eat any of it though, apparently he doesnt like Brussels sprouts? Why would you order an appetizer without asking me that youre not even going to eat? And why are you ordering a drink for me without asking what I want, and pick sour beer?

He proceeds to be a total jerk to the female bartender. When he leaves to go to the bathroom I apologize for him and explain its a first date, and she said she could tell. When he gets back, I say Im tired and Im going to get a cab home. He makes a move to kiss me and I nope out of there.



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You catch more flies with honey than with vinegar, or so the saying goes.

The same can be said for your interactions with cops, most of whom are perfectly happy to let minor infractions slide––When was the last time you were actually ticketed for jaywalking?––provided you're not a total Karen should you interact them.

Your local police officer likely doesn't care about jaywalking or the fact that you went five miles over the speed limit unless you give him a reason to, as we learned when Redditor Takdel asked police officers: "What stupid law have you enforced just because someone was an a-hole?"

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