Most people are on their best behavior during a first date—but that isn’t always the case. Some people just seem determined to put their worst foot forward, and we’re the ones left with our jaws dropped to the ground and searching for some way to just get out of the situation. These Redditors went on the worst first dates imaginable, and they lived to tell the tales. Read on, if you dare.
1. It Was Just Like In The Movies
A guy I’d been friends with for a couple of years asked me out. We knew each other, so we should have been able to have a fairly normal night out—but no. We met at a restaurant and sat at the bar. He ordered all meat appetizers despite me being a vegetarian and said, "You can eat this or go hungry". I ordered my own food.
Die Hard was just starting to play on the TV and he asked me if I liked it. I admitted that I had never seen Die Hard and he proceeded to describe the entire movie in real time. I am not exaggerating. I was not allowed to speak while he explained every single detail of the movie while the movie was playing silently on the bar TV.
I’d had too much to drink to leave early and drive home, so I just sat there and endured his two hour monologue while I slowly sobered up. When the movie finally, mercifully, finished, he asked the bartender for his check and said, "I’m not paying for her, though". The bartender brought his check and then told me I didn’t owe anything.
After my date left, the bartender said it was one of the most painful things he’d ever witnessed and apparently he and some of the servers had been placing bets about how long this guy would actually talk about Die Hard. I’m just glad I had a witness because it was so ridiculous. There was no second date and he literally never talked to me again.
2. She Couldn’t Hide
This red flag came up before we even went on our first date. So, I met this guy on a dating site and he asked me on a date and I agreed. Later, I got a call from work saying a package had been delivered. It was a huge bouquet of flowers. I was so confused. I asked him if he had sent them and he said, "I did! You said you had a bad day last Friday, so I wanted to make this Friday a good one for you".
Normally, I would absolutely love this gesture and be over the moon with this. But there was one glaring problem: I never told him where I worked, and I had told him I lived in a large city an hour away to be on the safe side. So, not only did he find my true town, but also found out where I had worked. This was an instant red flag and made me terrified.
3. She Wasn’t Exactly Daddy’s Little Girl
This woman and I sat down to dinner and within ten minutes she brought up how her father felt sorry for any guy that dated her. She continued for the next hour telling me about all the ways her father criticized her for playing games, and treating men poorly. I really didn’t get much of a word in.
After we left the restaurant, I drove her straight back home, while she continued talking the entire time. When she realized I’d stopped in her driveway, she asked me if she had said something wrong. I had to be totally honest with her. I said: "Yes, about two hours of wrong for me. Have a good night". And drove straight home.
4. They Met By Accident
This is what I knew about him before our first date: he had tragically lost his leg in a motorcycle accident. I also knew that he usually wore a prosthetic but at this time he was using a wheelchair. He said this was because he had recently had surgery in his leg. All that was fine, and I offered to pick him up in my car.
We went out for breakfast and everything seemed fine, there were no major issues with him. When it came time to pay, his card was declined. He called his dad—who was also his boss—to figure out why his paycheck hadn’t been deposited. This conversation went back and forth, and I ended up paying and he promised to pay me back. It totally wasn’t a big deal, it happens, I get it.
So, we got back to my car, which is a RAV4. He said that the last time he was around a RAV4, it was when his motorcycle accident happened. He’d hit into one that was pulling out of a restaurant and that’s when he lost his leg. For some reason, that triggered a memory of a conversation I had with my mom a while back about my aunt who had the same car which was totaled during an accident.
Later, I was texting him and asked him a few more questions about the accident, where it happened, and such. Long story short, it was my aunt who was driving the car that pulled out of the restaurant, which he crashed into. He was currently in the process of suing her because of it. This was despite the fact that he was going almost double the speed limit at the time and didn’t even have his license.
Needless to say, there was no second date. He never did pay me back for breakfast.
5. Mother Knows Best
I went on a date with a Korean-American guy in college, and it was really lovely. Lovely until his mother called during our coffee date. She asked him what my name was and he told her my first and last name. He suddenly got a sad look on his face and stood up, apologizing profusely for wasting my time. His reason blew me away.
He said: "I am so sorry, I should have had her look you up before the date". I was super confused. And asked him what he was talking about. Apparently he didn't realize my name was Japanese-American. The thing is, I am half-Japanese and don’t really look it. His mother had taken my name and found me on Facebook. There was a pic of me and my family at the Obon Festival hosted by the Buddhist temple and Japanese-American society in my city.
So, he left the date because his mommy told him he couldn't date a Japanese girl.
6. He Knew What She Wanted
I was at a restaurant on a first date and the guy had been to the restaurant before and made some recommendations about what to order. I wasn’t really feeling what he was suggesting, so I ordered something else. The guy then grabbed the waitress as she tried to walk away, and told her what I would have and, believe me, it wasn’t what I wanted.
It didn't even occur to him that she wouldn't listen or that I'd be angry. I got up and walked right out of the restaurant.
7. She Washed Her Hands Of Him
So, when I was in college, I met this guy at a work function. We also had mutual friends. The guy took me to a restaurant and before eating I pulled out a small bottle of hand sanitizer to use. He asked me why I used sanitizer. I thought the answer was obvious: to clean my hands. But when I told him that, he started explaining why hand cleaning was unnecessary.
He actually said that, in addition to not using hand sanitizer, he didn’t believe in washing his hands after going to the bathroom. He said it was fine as long as toilet paper was used effectively. He said all of this while licking his fingers and digging into a shared basket of appetizers. I was disgusted and stopped eating at that point. Not another bite!
8. He Hoped The Party Was Over
So, I show up for my first date with this guy and the first thing that I notice is that he’s brought his two year old along on our date. He then informed me he would be okay with me going out and partying for maybe one more year to "get it out of my system", but after that he expected me to settle down. He then went on a strange rant for my benefit.
He talked about how important it is for women to "have their fun" before becoming moms, so they are ready to be homemakers. I was 19 and also was not aware he even had a kid beforehand. Obviously, there was no second date. I recently looked the guy up on Facebook. He’s now on his third marriage. Hopefully, this wife got all of her "partying" out of her system.
Freepik,fxquadro
9. Something Fishy About This Guy
It was our first date and he and I were sharing a plate of raw fish. We both ate more of the salmon and it was running low. He then ordered me—in a rude way—to eat only white fish now. I did and was laughing, because I wasn't sure if it was a joke. After five pieces of white fish, I went back to the salmon, and he got annoyed and asked me why I’d done that.
He repeated that I should stick to eating the other type of fish with no explanation. He also ordered me to eat certain side dishes throughout the meal and I politely declined. After that, I made no effort to keep the conversation that—to be honest—had already been a bit awkward before this whole fish thing.
He seemed unsure how to fix the situation, and I kept my bad mood until I left. Just…why? Why did he do that?
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10. He Didn’t Just Lose His Shirt
I went out with a girl, we hit it off well to the point that things heated up and I spent the night at her place. The next morning, I awoke to an embarrassing surprise: all of my clothes were missing and so was she. It turns out, she had taken all of my clothes, including my underwear, with her to work. So, what could I do? I had no clothes and no way to leave her house.
So, I waited for her to come home from work. To her credit, she had cleaned and pressed my clothes as she worked at a dry cleaner. They were just jeans, a button up shirt, trench coat and underwear—but I appreciated the effort. She also replaced a broken button and a tear in the shoulder on my London Fog trench overcoat. This was also very nice and kind.
I was grateful for her efforts, but still put off that I had waited 10 hours for her to get home since I had to essentially stay in bed under the covers. In my mind there would be no second date. She was, however, my friend's friend, so I did see her from time to time when we went out, but I never went back out on an official date with her again.
11. He Made A Pit Stop
I was probably about 19 or 20 years old and incredibly naive at the time. I had known him for a few weeks, and we decided to go out on a dinner date. We were on our way to dinner—I was driving—and he wanted to stop to make a return at GameStop. I thought, "Yeah okay, no problem. I’m in no rush". But then he was in there for a long time, and I was getting kind of nervous. I should have paid attention to those nerves because trouble was headed my way.
When he finally comes back to my car, an officer comes out of nowhere and taps on my passenger window. The officer asked him for his driver’s license and went to run it. I asked my date what he thought was going on. This guy explains to me that he has some unpaid parking tickets. But the situation gets worse than that when another car pulls up and another officer gets out. He comes to my side of the car and pulls me out of the car and starts interrogating me.
The officer asking me questions assumes I’m in on whatever my date has done. Then I turn around to see—to my horror—my date getting pulled out of the car and cuffed. I was so shocked and now I was worried about myself. Would the officers believe that I wasn’t involved? I guess I looked legit surprised, so they started acting really nice to me. I was basically being honest and cooperative, and they could tell I had absolutely no clue what was going on. So, they let me go home.
I had no idea why all this had happened until much later. I looked at our local prison intake website and it turns out while I was waiting in the car, he’d shoplifted $500 worth of stuff from GameStop. He also had like three outstanding warrants for assault charges. Wow, I often imagine what could have happened if all this hadn’t gone down.
12. He Didn’t Get It
I went on a date once and the guy was talking about his ex-girlfriend the entire time. Then, it got worse. He actually took a call from her when we were waiting for our food to arrive. And when he was done, as a joke, I asked if he wanted to call her back and invite her to join us. He said no because she'd have to bring her kid! That joke went whoosh right over his dense head.
13. Nothing Compares To You
I went on a date with a guy who called himself a mama’s boy. I didn’t take that very seriously at the time, but I did later on in the date. He actually said that no woman would ever compare to his mother. Obviously, there was no second date, and despite how many times I turned him down and said I wasn’t interested, he kept calling and texting me for two years until I changed my number.
14. He Was Looking For A Replacement
I once met up with a guy from Tinder and I thought the date was going pretty well. After talking for a bit and having a coffee, he asked me if I wanted to meet his kid. I felt totally put on the spot and although I was clearly uncomfortable. I panicked and said I would. We went back to his place and I met the kid, she was actually pretty cool.
When he sent her off to bed, he proceeded to tell me that the mother of his child had randomly passed in their kitchen one day, and now his kid didn’t have a mom. I looked around his place and there were pictures of the deceased mom everywhere. I felt uncomfortable and I told him it was getting late, and I was going to get going.
Before I left, he asked if he could stroke my stomach and pinch my backside. It was a very specific and super odd request. I said no. The next day he sent me a text asking me if I would babysit his kid. Not even asking me on a second date…just asking for child care.
15. Not Even On Pizza?
I went out with a guy who was in his mid-20s. He told me a lot about himself that night, but one thing really sticks out to me. He told me he had never tried cheese. Not in his whole life. Not once. He wasn’t a vegan or anything like that. I had such a hard time believing him and realized I could never trust him. It’s been 10 years and it still bothers me.
16. He Was A Serial Dater
I met a guy on an app and, after we chatted for a while, we met up for drinks. Just to make small talk, I asked him about his Dexter tattoo. He actually had Michael C. Hall’s face on his shoulder. He said that what he liked most about Dexter was that he hid his true identity. There was an eerie silence after he said that.
Needless to say, I never saw him again.
17. He Was Literally Awful
So, I live in San Francisco and I went on a date with a guy years ago. We went to an art show together, which I thought was a nice change from going to a bar or restaurant. After the art show, we were walking in a park and talking and he did something that really shocked me: he littered. I said something like, "Oh there’s a trash can right over there". He just chuckled and said, "So what?"
I never saw that guy again.
18. He Expected Her To Pay
This guy I knew through a mutual friend kept asking if he could take me for dinner. I always politely turned him down because I'd just come out of a relationship and wasn't looking to jump into another. My friend convinced me that I should "try and get back out there and enjoy myself". The next time I ran into him, he asked if he could take me out again, so I relented and agreed.
The date went fine for the most part. There were a few awkward moments here and there but nothing that made me want to call it a night. Then, we got to the bill. He paid on his card and then told me, "Don't worry, I've got you covered. You can pay me back for your half when we get back to my place". He then made a winking gesture at me.
Needless to say, he made the journey back to his place alone and there was no second date.
19. Red Flag, Red Flag, Red Flag
This all happened during our first—and, thankfully, only—date. It literally kept getting worse, one thing after the other. When they brought the food, he immediately asked them to remake it, as it wasn’t cooked exactly how he wanted. When he got his second meal, he sent that one back as well and just ordered something else. This was the first red flag.
While we were eating, his phone suddenly lit up. I saw on the screen a picture of two young girls. So, I asked him if they were his nieces. Nope. He said they were his two daughters. One was two and the other was four years old. Funny, he’d never mentioned before that he was a father—even when I’d asked him directly. Red flag number two.
He then told me he still lives with his baby mama—who was his ex—and has no near plan of them living apart. Oh, and worse still, they live in his parents basement. He then randomly started talking about how much he hates the left wing because it doesn't favor white men like himself. These were red flags three and four. And the worst was yet to come.
He then proceeded to talk about how immigrants are ruining this country. If that wasn't bad enough, I'm middle Eastern and my parents are immigrants. This was definitely a huge red flag. We talked about traveling and he very nonchalantly said, "you probably have to leave so much earlier to the airport because of security eh?" This was a backhanded lowkey prejudiced type of red flag.
At that point the red flags turned into checkered flags telling me to end it and leave. So without any further responses from me, I grabbed my coat, thanked him for the free meal, and walked out.
20. Not An Animal Lover
I was on a date with this seemingly nice woman. We were just getting to know each other, and I mentioned that I had a dog. She showed some interest and asked me what kind of dog I had. I told her it was a Siberian Husky and that I loved her very much. Her response was this: "Oh! A big dog! At least she’ll die young, so you can get a puppy again soon!"
21. She Was A Real Doll
I was 24 years old and he came to the door to pick me up. I immediately noticed that he was carrying something and it wasn’t the expected flowers. It was a Bratz doll. An actual Bratz doll in the box, brand new. He actually went to the store and made a conscious decision to buy it for 24-year-old me. He told me he thought I’d like it. Did he want me to act younger? I don’t know, but he creeped me out.
The day after, he kept calling while I was at the grocery store, and I don’t like to talk on the phone while I’m shopping. I called him back, which may have been stupid. He asked why I was ignoring his calls. I told him the truth: that I had been shopping and I preferred to be able to interact with the people I needed to speak to—like the deli person or whoever—without being on the phone.
He immediately got upset and was mad and sad about how it wasn’t fair that the grocery store workers got that much of my time and attention, but he didn’t. That was the end of that.
22. Creepy And Shallow
I was on a date with a guy, and he immediately started making multiple comments about my appearance. To be fair, they were positive. The thing was that he delivered the comments in a very creepy and shallow way. He said things like: "I bet you look at the mirror and just think, 'wow, I’m hot'". And, "If I were you, I’d check myself out all the time".
He then told me about how he was taken in by officers in front of his old apartment and then evicted. After I told him I did not wish to go on a second date, his response was: "Okay, but first, I really want to take you to bed". This was a first date and I was 19 years old!
23. She Booked It
Someone I met through social media asked me out. We had a ton of friends in common, so I wasn’t too worried that he’d be a creep. We decided to meet at Barnes & Noble so we could get coffee and pick out books. We are both avid readers, so it sounded like a good place for a first date. He was crazy attractive and smart, and he seemed really into me. I was super excited.
So, we get there and within the first three minutes, he asks to kiss me. I agreed and it was….Wow. Instant fireworks. All the tingly feelings. We keep talking and things are going great, but then he proceeded to keep getting continuously more handsy. He was grabbing my backside, brushing the side of my chest while his arm was around me, pulling me by my hips into him.
All those things are great once you’re a little comfortable with someone, but not at the beginning of a first date. He kept only wanting to make out, and wasn’t accepting my brush-offs. So, 10 to 20 minutes in, I was starting to feel a little icky and kept saying: "Let’s just keep getting to know each other". He said something like, "I want to get to know you, but in the bathroom".
Honestly, that remark can be taken so many ways, but none of them are good. A pickup line involving the word bathroom makes me want to vomit. Eventually, I said I had to get going to work. He tried to convince me to quit my job and stay with him for the day. He told me we could go back to his place. When he said something along the line of "once we get married, you won’t need to work anymore anyway", I was out.
Nope, no, thank you. I told him it wasn’t going to work. He got super angry at me for "wasting his time" and bolted. By the time I got to my car, he had already deleted me from all social media. I’m still not really sure if he was angry that I didn’t want to do it with him in the Barnes & Noble bathroom, didn’t want to marry him, or if it was because I had a job. Maybe all three. Or maybe just because he was a moron.
24. Nothing To Think About
This first date was with a cell phone tower tech. He showed up for our date in an old, worn out—and sweaty—T-shirt. The guy immediately decided he could psychoanalyze me. He told me that I was afraid of men, despite me meeting him in a state park. He also told me he's tired of having steak dinners and ice cream and still not getting a relationship out of it.
He actually said that from now on, he was going to take his dates to the bedroom first—not an expensive restaurant. He told me that I had a lot to think about, and he would give me time. Nope, dude, I didn't have to think it over at all. Then, he told me his wife passed six weeks before our date—just six weeks! How did this guy get so jaded about dating in just a month and a half?
He asked if he could call me. I said "yes", but really I was thinking: "You can call, but I'm not going to answer".
25. He Didn’t Exactly Bowl Her Over
I was planning a first date with this guy a few years ago, and he suggested bowling. I said it was fine, but that I'd done it once a few years prior, and I was legitimately terrible at it. He offered to teach me, but I said another time. I just wanted to get to know him in a relaxed environment. He suggested we still bowl—minus the lessons—and he could also share in the hilarity of my lack of skill. I was down for it.
I arrived at the alley, and things went downhill fast. The lessons started almost immediately. He told me how to stand, where to stand, and pointed out everything I was doing wrong. He told me I wasn’t taking it seriously, and added this zinger: "I’m trying to teach you for your own good". While he taught me, he never smiled—except when he saw me at the start. I told him this was not the fun, chill night I said I was looking for, and he told me it would be if I took the game more seriously. He was actually angry about the whole night.
26. It’s Been A Slice
The setting of this first date was a pizza restaurant. I knew I was in for a bad date when the guy had the audacity to order for both of us. The pizza arrived, and he served me a single tiny slice of wood fired pizza that did not come close to filling me up. He then—before I could ask for a second slice—packed up the pizza and put it in the back of his car.
I excused myself to call a friend to come pick me up, because I absolutely would not let this man know where I lived. It's been almost two years, and I'm still angry about not having more of that pizza.
27. She Over Shared
On our first date, the woman opens her laptop and shows me a video of her giving "natural childbirth" in a pool with her ex-partner. She was full spread eagle, and it’s a closeup shot. I could see the crowning head pushing through and everything. Then, the now seven-year-old kid comes out to watch and is like, "Oh, I love this video!"
In other words, I’m not the first guy she’s made watch this. No second date.
28. A Real Mess In Aisle Three
I met a stranger at the grocery store, and he asked me out for dinner. Dinner didn't go very well, mostly because he spent most of the date insulting me for being a vegetarian. At the end of the night, when we were walking back to our cars and saying bye, he asked if he could have a kiss. I said no. He asked again. I said no again.
He then said, "How about a peck on the cheek?" Just to get rid of him, I go to do that. The guy fully turns his head and kisses me right on the mouth. This was the one thing I had told him I didn’t want. I definitely knew there would be no second date after that. I ignored all future texts. His last one said: "Why does this always happen to me?"
29. He Came To Save The Day
There was one date that stands out as the worst of all, but in retrospect it's kind of funny. I met this guy online and we had a few conversations before deciding to meet up. He seemed nice and normal, but when he showed up to the date he was wearing a full-on costume. He had dressed up as a superhero, complete with a mask and a cape. I was completely caught off guard and didn't know how to react. I tried to go along with it and make the best of it, but it was just too weird. I never saw him again, and I don't think I ever will.
Freepik,stockking
30. She Never Asked
I remember I went out on two dates with a girl when I was in my late 30s. She didn't ask me anything during both dates. She's very expressive and loves to talk. Even during texts she'd send hilarious memes and emojis that matched our conversation. But during dates, she wouldn't ask me a thing about me. That was a red flag that I should have acted on.
She loved talking about herself. There was never a "How are you", or "How was your day", or even "How was work?" Sure enough, when I said I didn't want to pursue her, and that we should just keep it as friends, she blew up at me and called me all sorts of names. One of which was "loser". She also said, "You jerk, I deserve better than you".
I remember just looking at her stunned and thinking this girl had some serious internal issues. I told her that she deserves someone better than me, because I for sure would not be able to handle what just happened. I told her she was overreacting because she's not losing anything, but that she would have an opportunity to meet someone else.
She then started blaming me for things I've never done. Like, "You're selfish, you only think about yourself! You never think about me! It's always about what you want to do!"
I told her, "You're talking to me like we were dating each other for two years! We only knew each other for two weeks!" I felt sorry for her, considering that she seemed like she had some emotional hurt that wasn't resolved from her previous relationship.
31. She Was A Little Crazy
I was meeting up with a woman I’d met online. Of course you always wonder if they’ll match their picture. Well, imagine my surprise when a woman who’s eight months pregnant shows up. A fact that all pictures and conversations had somehow managed to omit. We still went out because I wasn't about to dump a single, pregnant woman, but I really should have.
It turned out she was an off-her-meds, extremely depressed pregnant woman with suicidal ideation who proclaimed her undying and eternal love for me by hour one. And just a fun little side note: she was kind of short and so was her dad, who I did get to meet. Their house was on a farm and the whole thing was built to their height. I'm pretty tall and I felt like Gandalf visiting Bilbo.
32. Three Strikes He’s Out
I was on a first date and I told the guy I was working in the field of statistics. He quickly started talking about how that’s all pointless and meaningless. Um, that’s my profession we’re talking about. Later on, he asked how old my cats were, and I answered that they were 10 and 11. His reply? He said, statistically speaking, "they're going to die soon".
At some point during the date, I think it was while we were walking to the car, he blew out a nose full of snot. The guy didn't even ask if I had a tissue, he just turned around, blew it out, and kept talking as if nothing happened. He actually sounded surprised when I told him I didn't feel a good connection with him.
Freepik, stockking
33. This Little Fiesta Went Siesta
This was a summer date and it was super muggy out. We got tea and he wanted to sit outside in the sun. He kept going on about engineering and couldn’t take the cue that I wasn’t that interested. The next thing I knew, I had dozed off. I have no idea how long I’d slept for, but I was sweaty and warm and bored. The weird thing is that he kept talking while I napped.
Freepik, DCStudio
34. He Wanted The Full Package
I had met this guy on a dating app and agreed to meet him in a public park. The guy was an unemployed ex-serviceman and clearly had some mental issues, which weren’t super apparent when texting. As soon as we sat down to chat, he told me about his current terrible living situation and asked if he could move in with me and my kids. He offered to watch them for me while I worked.
I said this wasn’t a great idea and that's when he showed his true colors. He got so mad. I tried to explain and said that I didn’t really know him and we had just met. I was so annoyed that he even thought that it was okay to ask as I’m a very protective mom. The whole time he was very pushy and upset when I wasn’t just going along with whatever plans he already had in his head for us.
Near the end of the meeting, he could tell things weren’t going in his favor and asked if I had intentions of even dating him. I told him outright, "no". He again got mad and just left. Not long after that, I got a message from him saying he’d spent expensive gas coming to meet me, and I could have at least done it with him. Charming. Apparently, I owed him something since I wouldn’t provide him with shelter and financial support.
35. She Walked Away With It
This woman and I were having a great first date and ended up getting a little tipsy together and singing karaoke. She tricked me into showing her a ring I had inherited from my family. Somehow, being inebriated and merry, I completely messed up and did not realize she had kept the ring. She then made a fast excuse—like she needed to go get something or something—and left with the ring.
It turns out she lied about everything, even that she was from my city. I’ve never seen her—or my ring—since.
36. The Spy Who Loved Her
On our first date, he told me he was in med school, at the university in the town we lived in. This was a red flag as I knew there was no med school at the local university. I thought perhaps he was taking his pre-med classes or something, so I agreed to go on a second date. On this date, he spent an hour telling me how, when he’d finished with his army service, he had worked as a contractor for the army doing "spy" work in Iraq. He added ominously,"If only you knew the things I’d done!"
During the second date, we had to stop by his apartment to pick something up. While we were there, I noticed all his mail was in a different name than the one that he had given me. This made me super nervous, so I "magically" got a text from my work. I told him there was an emergency and I had to go immediately into work and handle it.
After I told him there wouldn’t be a third date, he got spooky angry. I hoped I would never see him again, but then the worst thing happened: I caught him in the bushes outside my apartment. This happened several times, so I eventually had to get a restraining order in the name he gave me. After that, I never saw him again! Thank God!
Freepik, wirestock
37. It Wasn’t A Good Fit
She wanted to have our first date at a shipping mall—which I thought was weird. When we met at the mall, she had her toddler with her. I have kids too, so I got it, but a heads up would have been nice. She told me that she wanted to shop for an outfit for her kid because she was doing a Christmas card family portrait later that week.
It was a bit uncomfortable, but hanging out shopping? Sure, why not. Then, she started holding up clothes to me and I stood back and asked her why. She said it was because I was "about the same size" as her ex and he was going to be in the portrait too. She then asked if I would try things on so she'd know how they would look on her ex. I took the clothes and walked off to "find the fitting room". Instead of finding the fitting room, I found my car instead.
I was very glad we drove separately, and I wasn't leaving her stranded.
Freepik, peoplecreations
38. He Had A Killer Sense Of Humor
I went on a Tinder date a few years ago. He made multiple creepy comments along the lines of "you know, you really shouldn’t just meet guys off Tinder. What if I was planning to kill you?" and kept trying to play it off as a joke. After the fourth time making that "joke", I started to feel really uneasy. It didn’t help that he was also just an unpleasant person to be around in general.
So, I texted my friend to call me with a made up emergency, so that I had an excuse to leave. He dropped me off at her house, and I thought it was all good. But that's when things took a frightening turn. He got out of the car and walked right into the house. At this point my friend told him he needed to leave. He said, "Alright, fine, I’ll leave", and then just continued to stand there staring at us.
We then asked him again to leave. He said he’d leave but he wanted me to walk him to his car. Obviously, this dude was acting super bizarre, and I was scared if I didn't just go along with what he said that he might lash out. So, stupidly, I said I’d walk him to his car. So, we went outside and got to the car and then he just stood and stared at me again.
I said bye and then quickly started to walk towards the house. All of a sudden, he very angrily demanded that I hug him. At that point I literally just turned around and ran into the house and locked the door. The guy sat in the car outside for like 10 minutes texting me super angry stuff about how he won’t leave until I give him a hug and a kiss.
After getting no response from me whatsoever he finally left. So, yeah I guess you could say that was a bit of a red flag.
39. It Was Bad From Five Minutes In
I was married for nine years and then got a divorce. I wasn't really ready to start dating, but some friends convinced me to. My first date after nine years was a complete disaster. We met at a restaurant and five minutes, in she told me she ate a sandwich in the car because she wasn't sure I would be able to pay for both drinks and food.
Seven minutes into the date, she advised me that food service was a good field because they rarely look at people's records—even after what that lying boss of hers at Little Caesars said about her. Fifteen minutes into the date, she told me that I didn't need to worry about her around my kids because she’d never be inebriated around them. She felt compelled to add that she might be buzzed around them but never full-on inebriated.
Twenty minutes into the date, she said she liked me because I looked clean. With the last guy she was with, she had hurt her ankle by slipping on some pizza he had on his bedroom floor when they went to get it on together. The pizza on the floor, however, didn’t dissuade her from doing the deed. Despite the urging—nay, pleading—of all my friends, we did not go out again.
40. That Don’t Impress Me Much
One time, a guy opened his wallet to pay the bill and made a point to open his wallet wide enough to flash a wad of hundreds with a smirk on his face while looking me dead in the eyes. It was an instant turnoff for me. To think that all I care about is money and that it would impress me somehow. Impress me with your personality, sir.
41. She Had It Down To An Art
I went on a date with a girl who worked at a well known local art museum. She talked about art in the most technical, plain, boring, dry terms imaginable, and I could barely follow along. I asked questions, and she made me feel like an idiot. I tried to talk about art—which, incidentally, I love—and was again treated like an idiot. Needless to say, there was no second date.
42. She Waited Six Minutes
I was on a date with a woman and it was only six minutes in when she asked me how much I earned. When I asked why that was relevant, she said she had no intention of working once married, so she wasn't going to waste her time with someone earning less than X amount. I’ve now forgotten the amount she gave, but I remember it being very high, and nowhere close to what I was earning at the time.
I said, "I don't think this is going to work, then". She sighed and said I was another broke loser who thought I could get girls when I wasn't prepared to support them. I noped out of there.
43. He Had A Temper
I once went out on a date with a guy who I’d met on gay.com. He asked to pick me up, which was fine. He picked me up and proceeded to road rage at absolutely everyone for any reason whatsoever. At one point, his head was out the window screaming profanities at an innocent family in a van, who had not even slightly cut him off. I was so scared.
44. One Word: Yikes
A few weeks after my first husband and I separated, a friend decided I needed to get out and set me up on a blind date. I wasn’t interested or ready, but she was so sure this guy would be perfect for me to ease back into dating (not that I had any desire to do that just then) and begged so hard that I agreed.
I met the guy at a restaurant not too far from my home. He wanted to pick me up, but I wasn’t going to do that for a blind date. He was waiting for me and seemed nice enough. We ordered and began to talk.
He actually did all the talking. He told me how he’d been divorced for 5 years at that point (ok…not a problem)…and he still talked to his ex-wife (also not a problem)…who was dating. And now the fun begins.
He told me that he regularly parked outside his ex-wife’s home so he could see if anyone visited her. And if she brought a guy home, he’d go over and pound on the door until she answered. Then he’d force his way in and threaten them both, until someone called the authorities. He’d done this three times already!!
After all this, the guy actually suggested going to MY house for a nightcap. I declined, on the grounds that I had to go meet my mother and pick up some papers for a club we belonged to...And I left. Quickly.
Then he followed me.
So, I drove to the nearest freeway on-ramp and took off. Thankfully, there weren’t any cops around because I was exceeding the speed limit by a fair amount. I took the next off-ramp, drove on surface streets to the next on-ramp going the other way, and headed back home. But I DID stop at the local station car park for a bit, just in case. Then I drove to another car park, pulled into a dark corner, and watched, just in case.
I didn’t go home for another half hour. Then I immediately called my friend and told her if she gave him my address, I’d really never speak to her again. Once she found out what happened, she wouldn’t speak to him anymore, either.
And he sent flowers to both of us at our work the next day! We threw them away.
45. Free Tats
I started talking to a guy over Facebook Messenger who was a tattoo artist about to open up his own shop. He invited me to come chill at the shop while setting stuff up. I hadn't even been there five or 10 minutes when he started questioning if I told anyone I was there, or where I was going. And if this wasn’t weird enough, it was about to get weirder.
He started asking what tattoos I wanted next and offered to give me a free tattoo right then. And then he tells me that if I'll be his girlfriend, he'll give me all my tattoos for free. I came up with an excuse to dip out fast. It was so bizarre, this dude was a seriously good tattoo artist. I kind of kick myself for not getting the free ink when I had the chance. He was pretty attractive, too. If he had not acted like a creep straight off the bat, he would've had a very decent chance of scoring.
46. On A Scale from One To Ten: You Suck
There was a guy who I was considering hooking up with. That is, until he said the following: he told me over and over again that I was a solid 7.5 out 10—at best. He said this was okay because most guys lower their standards as they are typically only requiring a six and above for marriage potential. Yeah, I was done after I found out he wasn't joking.
47. Temper, Temper
I was on a first date with a guy, and things were going okay. I went to the bar to get another drink, and the bartender wrote a CD recommendation on a piece of paper for me. When I got back to our table, my date said, "Did you just give that guy your number?" I was shocked and told him, "no", and that I’d just swapped music recommendations with him.
The guy got super angry and said that he was going to knock the bartender’s block off. I couldn’t help but make a comment about this guy’s bad temper. He agreed with me and told me about a time he got so angry while in traffic that punched his fist through the windscreen. He had scars to prove it. That was a big nope.
48. She Had Two Choices
This happened when I was in college. I was hanging out with this guy in a state park during the night—I know it was a terrible idea. It was going alright until out of nowhere he said: "Don't you ever have the urge to hurt people in very bad ways?" Imagine being with a guy in the middle of the night in a park where nobody is around you and suddenly you hear that. Yikes!
So, suddenly, I wanted to get away from this guy. But there was one big problem: I didn't know my way back to the dorm room. I asked him to help me, and he said he wouldn’t. He gave me two choices: I could figure out the way back by myself or I could spend more time with him in the woods. He then took my phone, so I wouldn’t be able to check the Maps app.
I can't believe how naive I could be sometimes when I fall for someone. I am so glad nothing bad happened.
49. Stamp Of Disapproval
Years ago, I went on a first date with someone I met online. We met at a bar and the bartender carded us. Even though we were both older, they were still doing stings in the area, so he was carding every single person. I handed mine right over, but my date was a real jerk about it. The bartender checked mine and handed it back to me.
Then, he checked my date's ID, and rather than handing it back to him, he placed it on the bar right in front of me. When I saw it, my blood ran cold. It had an "intimate" offender stamp on it, which is a thing in my state. The guy picked it up, looked at the bartender, looked at me, and then got up and walked out. I immediately Googled him.
He was on the registry and had been in prison. Lesson learned. Always Google. And that bartender? We’re still friends.
50. Her Dance Card Was Full
I was set up on a blind date with a woman who possibly had some issues mentally. When I got to her home to pick her up, we sat around in the living room before we left for dinner. Unfortunately, all she did was talk about her boyfriend who, two years previous to our date, had lost his life in a car accident. Apparently, he’d been driving too fast and was over the limit to operate a vehicle.
After telling me about the accident, she excused herself to go get something. That's when the date turned into a creepshow. She came back with something that had belonged to the guy. Something she had kept to remember him by. To my horror, it was a blood soaked book from the day of the accident. It was very creepy. Even though this was a huge red flag, I decided to go ahead with the date.
We went to the restaurant and sat and talked and enjoyed our meal. Our meal was about midway through, and we decided to pause and enjoy a dance together. After we returned to our table, some stranger came up and asked her to dance, and she said yes, which surprised me, but I decided just to be chill about it.
An hour later, she hadn’t come back from dancing, so I just got up and walked out. I figured she was having more fun with him, so he could give her a ride home. I think it took her a long time to notice I was gone. Looking back, I could have handled that better. And I don’t like how many times I’ve had to say this in my life: "Could’ve done better".
51. Father Of The Year Award Goes To…
He brought his two kids on the date, and then, in full earshot of them both, adamantly told me not to have kids and started complaining about the kids' mother. I stopped dating after that. I don't regret that choice.
52. She Only Got A Hug
So, I went on a date with a woman who spent most of her time on her phone. At one point, I even stopped mid sentence to see if she'd notice. She did not. She didn't have any money, so I was buying all the drinks. Then, it just got worse. She started asking me if I wanted to buy some illicit substances with her. To top it off, she called her ex right in front of me.
I put on my coat and started to leave, and she started crying. We talked briefly, and I gave her a big hug and asked if there was anything she needed. She replied with: "Maybe a tenner?" I walked straight out of there. Later, she texted me, asking to see me again. There was absolutely no way I was going to see this woman again.
53. He Was Honestly Quite Scary
It was our first date and we met up at his place because he was making dinner for me. We were chatting on the couch when he stood up to excuse himself to the restroom. As he was walking away, he turned and mentioned that there were cameras all over his home, so "don’t take anything". I guessed this was a joke, but what he did next sent chills down my spine.
He pointed to a stack of papers on an end table. "I believe in honesty. That’s my arrest record. Everything is right there". He went on his way. I considered leaving right then, but didn’t. I did pick up that stack of papers. It was a shocker. His arrest record was several pages long and spanned three states. Most of the arrests were for domestic assault. There were also some minor drug charges.
He returned and, thank God, my phone rang. I answered it even though I didn’t recognize the number. I actually had no idea who it was. I made it sound like it was one of my daughters and she needed to be picked up from somewhere immediately. I’ll never know who was actually on the other end of that call, but I left this guy’s home and never looked back.
54. He Loved Radio
So, my date came in, and first thing off the bat said he recognized me from my acne scars. They’re not that bad, in fact, they're very minor. We moved to a coffee shop and halfway through coffee arriving, suddenly, he just jumped out the window. It was a low, large window, so this was pretty easily done. Once he landed on the sidewalk, he legged it up the street.
I sat there in literal disbelief for ages unsure if I should pay the coffee tab or what even happened. He eventually came back. Apparently, he’d recognized his favorite D-grade radio celebrity walking past and just had to go and tell them how much he loves them. He was raving about how exciting this was while I sat there dumbfounded.
Freepik, wayhomestudio
