A Good Date Instantly Ruined

August 23, 2023 | Nia Williams

A Good Date Instantly Ruined

Dating is such a hit-and-miss game these days. That’s why first-date impressions are so important. These Redditors share their unfortunate stories of how their first date got instantly ruined by the other person. From inviting their parents to having their boyfriend show up, it’s hard to believe that people like this actually exist. But yeah, they do.

1. Not Staying For A Refill

She told me she had pretty bad anxiety being in public and asked if she could make me dinner instead. We went for a walk prior to the dinner so we could see if we wanted to do the dinner after. She was super stoked for dinner after our walk.

Dinner was great and she asked if I wanted to watch a movie. About 20 minutes into the movie, she started nudging into me and initiated making out. After starting to really get into the heavier side of things, I felt something tap my shoulder—I am on top of her at this point. 

Startled, I turned my head quickly. I can't believe my eyes. I am met eye to eye with a 4-5-year-old boy who then asked me if he could have a cup of water. His mom started screaming at him to go back to his room, which he did. She started apologizing and tried to reinitiate the kiss. 

I told her to give me a minute. I got a cup of water and called for the boy to come back out. When he did, I handed him the cup. He took a drink and said thank you and ran back into his room. I was pretty riled up at the idea she had her kid there without saying anything AND screamed at him for asking for something as basic as water. 

I left after that and vowed to never be that parent with my own kids.

date fails

2. A Sign To Move On From HIM

I was out with a guy having a lovely time when he made a comment about a copper bangle bracelet I was wearing. I told him that it was really special to me as I had gotten it during my semester abroad in South Africa from a local. 

It was a solid copper band, but in the middle there was copper wire woven around. He asked to take a closer look so I took it off and handed it to him. He then snapped it in half, thinking the copper wire was a spring. But that wasn't all. I was visibly upset and he said that it was a sign that I needed to move on from my trip and stop living in the past. 

WHAT? I never spoke to him again.

Man is arguing with woman outside.Keira Burton , Pexels

3. Jaw-Dropping Moment

I was out on a dinner date with a gorgeous girl. We had a lot in common and we spoke for an hour.

When it was time for us to hit up the arcade, I asked for the check so I could pay for dinner. As I put my card down, she put her card down as well and said that she’d pay for her half of the meal. I INSISTED that it was fine for me to pick up the bill but she refused. 

She said that she would pay for her meal. Fast forward to the end of the night. After being at the arcade, we were walking back to our cars. She looked at me and said, “It won’t work between us”. I said, “That sucks, why?” And she said—“As a man, I expected you to pay for our dinner tonight”.

I seriously wish someone recorded my facial reaction to that sentence. Was I expected to grab her credit card and throw it back at her?

andreas , Freepik

4. Three’s A Crowd

We were out for dinner on our first date. Everything was going really well so we decided to head over to a bar close by for a couple drinks.

We were there for a little bit. She saw a friend of hers from work who came over to say hello. She ended up sitting down to join us. It wasn’t a big deal at first, until the entirety of the conversation ended up being about ins and outs of work and gossip about their co-workers.

There was pretty much nothing for me to add or participate in the conversation about aside from just changing the subject completely. After about 45 minutes, I just said I was getting tired, said goodnight and left. Then came the piece de resistance.

What made it worse was that as I was leaving, a group of my friends—who I probably would have tried to meet up with—were coming into the same bar. I still left to stick to the story and because she had tried to convince me to stay.

Young bearded man is seating at bar with friends having a drink.cottonbro studio , Pexels

5. I’m Dang-Near Speechless

Our first date was amazing. I still reminisce about how incredible that night was and how incredible I thought my life was about to become. But the afternoon before what was supposed to be our second date, I got a voicemail: "I know you went out with my fiancee last night. I'm not mad at you. I'm sure you didn't know I existed—but I do, and I'd appreciate it if you stopped seeing her".


Sad man is seating on the sofa and talking on the phone.RDNE Stock project ,Pexels

6. I Swear I Didn’t Plan That

We had dinner and all was going well. Afterwards, we were wandering down the dark sidewalk engaged in conversation, when she walked straight into a signpost that neither of us noticed. I let out one nervous laugh before I could stop it. She accused me of engineering the event for my amusement.

Elegant young couple is standing by the light post at night.freepik, Freepik

7. Don’t Cross My Boundaries

I went bowling with a guy and a couple other friends. We were getting along pretty well until my friend got up to bowl and we were left sitting alone together. That’s when he put his hand on my thigh.

I wasn't into physical affection from people I don't know well. I wasn't comfortable with him yet so I politely and subtly scooched his hand away so as to not bring attention to it and embarrass him. 

That in itself wasn't an issue because he tried his luck and why not? His response was what infuriated me. He put his hand BACK and gripped my leg assertively. I wasn't having it and figured he just didn't get the hint. So I picked up his hand and moved it back to his own lap. 

He shot a look at me and then dove his hand into my inner thigh. I grabbed his wrist and pulled his hand out and looked over at him with the most definitive "NO" on my face I could. We did not go out again. If a man can't respect my physical boundaries in public, he sure as heck won't respect them in private.

Young couple are seating at bowling alley next to bowling balls.cottonbro studio , Pexels

8. This Smells Off

We were at a fancy restaurant for a first date. Both the dinner and conversation were going well. Then under the table, he slipped off his shoes and pushed them forward toward me.

Oh man, they stunk! I used a foot to push them back to him. He kept talking and pushed them back toward me under the table.

Why the heck would you pop your shoes off in a nice restaurant? Why would you push them toward your date? Why wouldn’t you do something about stinky shoes in general?

Woman is looking around at restaurant.Katerina Holmes, Pexels

9. We Just Met

He asked if I would stop seeing other men because his most recent ex had cheated on him, so he now wanted to be sure that anything new would be strictly exclusive. That was totally fair. I prefer monogamy myself—except this was about 30 minutes into our first meeting. 

We were only grabbing coffee after having met on the apps a couple days prior. I wasn't even chatting with anyone else at the time, but I wasn't really into having my actions controlled by a man I just met. I especially didn’t want to date someone who was clearly ready to let his ex's actions determine his treatment and expectations of me.

I hope he has managed to heal from that relationship since then, though.

Couple are seating and drinking coffee outside.Vlada Karpovich, Pexels

10. Let The Ink Dry First

I was on a date with a newly divorced woman. We were having a nice dinner and getting to know each other. Then it turned awkward. She didn't tell me she had kids until we were eating dinner. Things started to move much too fast after that.

She started talking about me meeting her kids right away, moving in together, etc. This was on our first date! I didn't want to be anybody's step parent, much less get U-Hauled so quickly.

We finished our dinner and parted ways amicably. After a heart-to-heart talk, there were no hard feelings. She was simply getting carried away with the excitement of being single and going out with new people. She agreed that she needed to let the ink dry on her divorce a little longer and take her time before introducing new people to her children. We fell out of contact soon after.

Man is smiling and having lunch with woman at restaurant.Gary Barnes, Pexels

11. No Idea What Happened

I asked a Korean exchange student out in my first week of college. I had never actually asked anyone if they wanted to go out before, so my jaw dropped when she accepted. After all, she was gorgeous and way out of my league. 

Two days later, I picked her up at her dorm in my fairly new Mustang. She seemed quiet, and I thought it was just shyness. We're on the highway doing 55 miles per hour. Disaster struck hard and fast. She suddenly rolled down the window and VOMITED ALL OVER THE OUTSIDE OF THE CAR—like—a lot.

I think she ate a gallon of vegetable soup before the date or something. I took her back to her dorm. She ran out of the car and I was left to clean things up. I took the car to a car wash and it actually faded the paint.

This was before cell phones, so I tried finding her to talk to after that. I never saw her again. That was back in 1990. To this day, I have no idea what happened.

metamorworks, Shutterstock

12. That Was Unexpected

I was around 22 or 23 years old and was meeting a guy for my first date at a restaurant for dinner. When I got there, I saw two other people at the table. It turns out, he had invited his parents to our date! 

I excused myself to go to the bathroom and then just bounced. Talk about awkwardness. 

freepik, Freepik

13. There Won’t Be Seconds For Me

I met a guy on Tinder. We chatted for a while. He had a great personality and seemed nice!  We met up and had a drink. He was funny, well-dressed and seemed to be into me. We decided to walk over to another spot where we could grab something to eat. 

He stopped at a corner store to grab a chapstick. Not a problem—sometimes you need chapstick! Then it all went so wrong. After buying it, he unwrapped it and dropped the box on the counter in front of the cashier. The cashier and I looked at each other, utterly confused. 

The cashier pointed to the garbage can by the door and asked him to throw it out over there. The guy rolled his eyes, snorted, and walked it to the trash. That's when I knew I wasn't going to be calling him back. 

There were other signs at the next spot, but that's when I was pretty sure he was probably one very inconsiderate individual.

Couple are walking inside a store and looking something on the shelfs.i_am_zews, Shutterstock

14. Dinner Ended Along With My Interest

After I got divorced, I went on some dates to try to meet new people.

When meeting someone new for the first time, I would always invite them to do something kind of noncommittal like getting coffee. That way, if things got a bit weird, I could end things early and leave.

So on this date, the girl shows up with her two young children, who I didn’t even know existed. That wasn't a problem for me and she was super nice. We talked for about twenty minutes outside the coffee shop. Then I suggested we do something more kid-friendly like getting ice cream. Everyone loved the idea.

We found a nearby place and went there instead. The kids were happy and we had some really good conversation for about an hour. I asked if she would be interested in dinner. She said yes but it would have to be several hours later and that her kids may have to come too as her sitter had bailed last minute. 

Later that night, she and her kids met me at a low-end steak house. We got along great and the conversation was good still! But then she got sloppy and inebriated off the three drinks she ordered with dinner and then drove her kids home afterward—I did offer to pay for her to get a ride home, which she refused. 

That just ended any interest I had.

Woman is smiling and making a toast at dinner seating next to her daughter.freepik, Freepik

15. Those Aren’t Tears Of Joy

I met a single mom at Denny's. We were both getting along pretty well, talking about our families and things. I mentioned that I didn’t get along with my dad because he's a narcissist. That’s when she said, "So is my ex" and immediately started crying.

For the rest of the date I was her psychologist.

Man is standing next to a crying woman and looking at her.Pavel Danilyuk , Pexels

16. Front Row Ticket For One

The date went really well. We went to a bar and talked a lot. Afterwards, she invited me back to her place, which was not far away from the bar. 

As I walked through the door, she asked what movie I would like to watch. I remembered that I hadn’t seen The Prestige and suggested that. 

It turns out, the movie got so interesting, tipsy me started rejecting her advances. I didn’t want to miss any of the good parts of the movie! 

Couple are seating on the bed and watching a movie.cottonbro studio , Pexels

17. Too Much Attention

I went on a date with a guy who owned a local trendy business. It kind of made him a bit of a local celebrity. Notably, I am an introvert and don't like attention. I’d much prefer to pretend that I was invisible when out in public.

We were on our second date at a restaurant. It wasn’t super fancy but it certainly was a little romantic place for a date. During our dinner, no less than five random people stopped by our table to talk to him. They were all customers. 

He tried to balance being an attentive date without totally alienating his customers. It was super awkward. He was aware that I was an introvert and was apologetic about it. He suggested that we wrap up dinner, hit up a store to grab some drinks and dessert and go to the beach—a good way to be around less people. 

In the shop we stopped at, two more people came up to him to chat, and then at the beach another person stopped and this one actually tried to sit down to join us. At this point, I decided this guy wasn't for me. I really liked him as a person but I couldn't deal with all the attention he attracted. But there's a twist.

Somehow, he convinced me to go on a third date, which I am glad he did. It's been 20 plus years that we've been together. He's helped me come out of my shell a little and I've taught him the delights of being an introvert and taking some completely people-free weekends. He is my person and I love him more than anything.

Young woman is seating on the beach next to a man wearing blue jacket.Beata Nykiel, Pexels

18. Letting It All Out

We were having a great time. We had a couple of cocktails, we were laughing constantly and flirting. I don't think I've ever hit it off so well with anyone.

I hadn’t been home long after returning from Afghanistan. She asked about the temperature out there. Then two minutes later, I started crying my eyes out and all the feelings I had bottled up came pouring out.

She got all the details that she never asked for. It was awkward to the point where she couldn't leave me as I kept talking and crying—for almost two hours.

We had an hour of hilarious drinks followed by an hour and a half of crying.

Man is crying and talking with girl.SAULO LEITE , Pexels

19. Poor In Judgment As Well

When my date turned up, he immediately asked what I wanted to drink. I chose a stout, then went to the toilet. When I returned, it wasn’t the beverage I had asked for. So I asked if they didn’t have the one I wanted? He said that this one was cheaper. 

Okay. I was slightly baffled but he was a student so I let it go. He proceeded to talk about how broke he was. I wasn’t much better off but felt deep guilt so spent the rest of the night footing the bill. I didn’t mind as he was cool and we had a lot in common.

When it was time to go home, he walked me to my bus stop. Then out of nowhere, he randomly pulled out 20 dollars. He went to get a kebab without so much as an offer for me. I was actually cringing inside. I knew that I wouldn’t be seeing him again. 

When I got home, he sent an unsolicited picture inviting me to see him again. See him again, I did not.

Young woman is seating on the table with man ,drinking coffee together and smiling.NATASHA LOIS , Pexels

20. Bored Of Games

Things were going really well. We were at a bar having drinks when she decided that she wanted to play Scrabble. Apparently, she loved the game, which I am not great at. On top of that, I’ve had a few too many. I was completely not ready to play Scrabble.

She started with a word like “behooves” or something. Meanwhile, I used up my entire time to put down the word “hat”. She then put down the word “incredulous” followed by my “fun”. This continued until the end of the game.

We did not play again. We did not go out again.

Toy bricks on the wooden table with word Racool_studio , Freepik

21. Beautiful But Rattled

I went on a blind date with someone who had “just gotten out of a bad relationship”. When she first showed up, she looked really rattled. She was beautiful, but shaken up. I asked if she was okay and she said she was fine. 

But when a tall guy passed too close by her chair in the restaurant, she practically jumped out of her skin. She finally admitted the horrible story. She had been “dating” her cousin. Yes—her cousin. They were really “into each other” but she finally called it off because she knew it was wrong. 

He wasn’t happy—it didn’t seem like she was either. It was a shame because she was gorgeous but her mind was a million miles away the whole time. When the date was over, I went to drop her off in front of her apartment complex. 

That’s when I noticed a tall, good-looking guy leaning against a car out front. She gasped and said, “That’s him”! I asked if she’d be okay, if she wanted me to walk her inside or take her somewhere else. She said that she was fine but I might want to leave ASAP. 

She then proceeded to practically leap into his arms as he strode towards us. As I drove off, I saw her get into his Tesla.

Young couple is seating in the car and looking outside.freepik, Freepik

22. Never To Be Seen Again

After dinner, we went to a bar. Everything seemed to be going well. We had a good conversation and we made out. The bar was getting really busy for some reason so we decided to go back to my place. Before leaving, I told her I needed to go to the restroom first. She said she would wait for me outside.

When I was finished, I went outside to look for her. I saw her just as she was jumping into the back of a pickup with a bunch of people and leaving. 

She later texted me saying she bumped into her best friend and they were going to a party but they didn’t want me to go along. I never saw her after that.

People are dancing in the back of a blue pick up truck.Jacob Lund, Shutterstock

23. Painful Slip Up

We met on a dating app in college during the last week before winter break. Once we realized that we lived close to each other, we met for coffee in a nearby cafe. After the coffee, we decided to take a walk around the city. Being winter, it was a snowy day with ice on the ground.

At some point during our walk, I made a joke and she playfully pushed my arm. This small moment changed my life. Unfortunately, I happened to be standing on a sheet of black ice at the time. I slipped and tore both my ACL and MCL.

I ended up spending the next six months on crutches. It wasn’t really her fault of course, but that definitely ruined the date.

Young couple are walking outside on a road with snow.Leah Kelley, Pexels

24. The Look Of Panic

It was my first post-divorce date. That poor guy. He had no idea what he was in for. I think I did all the textbook things of what not to do: talked endlessly about my last relationship and drank too much. I was a certified hot mess.

The absolute cherry on top was when he dropped me off at home, I repeatedly asked him if he was going to call me. I could still see the look of pure panic on his face. Shockingly, he did not call. That was our one and only terrible date. 

Woman is standing and looking back next to a man at bar.cottonbro studio , Pexels

25. I Got The Hint

We went out for drinks and had a great conversation. Afterwards, we went out for some food at a late night sub place. We were still having a good time and started getting flirtatious. Suddenly, an intoxicated dude walked past the table, stopped, and looked at her. 

He then said, "Dang it girl. Let me get your number". He then turned to me and said, “Oh man, my bad bro. Is this your girl"? I was stumped. I didn’t know what to say. If I said, “No”, it's like I was denying her. If I said, “Yes”, well it's not true.

I didn't know how to handle it and I ended up saying, “We just met". He walked on and kept saying, “My bad—bro don't mess me up". The conversation went cold after that. She asked to go home and refused my offer to walk her to her car.

I texted her the next day and said that I had a good time. I apologized for the awkward ending. I asked if she wanted to maybe grab a coffee sometime. She replied, "Sure". I said, “Cool, I'll hit you up sometime". She said, “Cool" and that was that. Her previous texts were wordy. I could take a hint.

Man is looking sad ,seating next to a girl looking at side.cottonbro studio , Pexels

26. That’s Not Cool

I went on a nice date with a girl. In the morning, I was driving her back and we were talking about how far she lived. She mentioned that it didn’t matter because she would drive even if she was intoxicated. I asked why she would do that as it was very irresponsible. 

She said that she used to do it in Idaho all the time so she expected to get a ticket for drinking and driving at some point. Like, what?

Young man is driving a convertible car with girl seating next to him.Roberto Nickson, Pexels

27. Ultimate Turn Off

I met a great looking guy on a dating app. We decided to meet at an Indian restaurant close by—my favorite food.

The conversation was great. We were laughing. He was kind of flirty and I was flirting back. He was really super cute, fit, and financially well off—all the good stuff. Then came the kicker. I don’t know how I just sat through this, but he started making fun of the waiter. 

Then the waiter's accent; the way he moved; the way he talked. My face just went blank and then did this little mouth thing that I do when I’m kind of upset. And he was like, “What?”

I told him that I didn’t think that it was cool at all. He didn’t get it and said that he was just having fun. I told him that it’s not fun. So in the parking lot we said good-bye. I had offered to pay for my own meal, but he would not agree to that. And he said, “Yeah, butterfly. You owe me dinner”.

Yeah, I don’t owe you anything. Such a turn off.

Woman is standing and looking at young black man who is looking at side upset.Dziana Hasanbekava, Pexels

28. Now That Was Rude

We were on a date having a good time—at least I thought so, until one of her friends showed up and invited her to a band playing across the street. She said that sounded awesome and left. There was no apology, invitation, reschedule—nothing.

I get if you weren't enjoying the date but some common courtesy would’ve been nice.

Young man is seating alone and drinking coffee.Balljinder Singh, Pexels

29. Too Weird For Me

We went to her house and started watching the movie Fight Club. This was about 15 or 16 years ago. It was a pretty cool movie at the time. 

We were in the middle of being very intimate when she suddenly shouted for me to "STOP"! I asked if everything was okay. She just shushed me and started watching the movie again. We were at the part where Brad Pitt burns Edward Norton's hand with chemicals.

I'm on top of her and trying to stay intimate. Meanwhile, she was watching intently and was completely in a trance. When that part of the movie was over, I asked her what was going on. After a series of questions, she made a horrific revelation. She explained that she enjoys watching people being in pain but not inflicting it or being in pain herself.

Needless to say, I didn't hang out with her again.

Young man is looking at camera with surprised face.cookie_studio, Freepik

30. Yep, I’m Outta Here

I had just turned 18 in high school and hit it off with this girl I met on Tinder. On the date, things were going well. We had similar music and movie tastes, we both loved animals, and so on.

At one point, I asked what she did for fun during the past week. She told me that she got blackout smashed with her friends on the weekend. Although I wasn’t at the lawful age at the time to drink, I didn’t mind if the person I was seeing drank at all. I let her tell her story and the conversation continued.

Later in the date, I asked her what her plans were for the coming weekend—in an effort to show continued interest in going on another date. She told me that she planned on going to a club and getting blackout all weekend with her friend. 

Hmmm, okay. So I asked, “What about next weekend"? She then says that she knows that she’s going to get completely plastered with her friends at another different club. For me, at least, that was enough for me to straight up say that I did not think things were going to work between us. I quickly finished the date and left.

Young couple are seating and having a breakfast outdoorSamson Katt , Pexels

31. Freaking Out

I'll start off by saying that I was on a date with a guy who was very handsome, smart, funny, and respectful. Our coffee date was going well. We were laughing and everything—until his ex showed up.

He saw her and started getting paranoid. He kept saying, "We gotta get out of here. We gotta get out of here" and started just freaking out. Of course we left, but I never went out with him again.

Young woman is having a coffee in coffee shop with man looking at her.Juan Vargas, Pexels

32. That Was Super Uncomfortable

He made a weird, seductive joke when we were buying food and snacks together. He said something like, “I’ll give you a snack later” and started laughing to himself quite loudly. Other people heard the whole thing too. It made me super uncomfortable because I’m not into stuff like this, or moving fast in relationships. I lost all interest in him pretty quickly.

Young woman is looking at side with surprised face.Polina Zimmerman, Pexels

33. So Distasteful

He showed discriminatory behavior towards our server, then he wanted to get a pat on the back for it afterwards. When he realized I didn’t agree with what he did, he reply was so stupid. He didn’t stop being an idiot. He simply looked away but continued being clearly both annoyed at the server AND me.

I paid the bill directly to the server with a good tip, apologized for the situation, and skedaddled. Nope.

Couple are arguing with a waiter who is standing next to a table.Fancy Studio ,Shutterstock

34. Let’s Cut This Date Short

The date started normal and fine. I was visiting town and wanted to have some fun and found him on Tinder. He was taking me to a bunch of different bars in the area that he liked.

Then randomly halfway through our date he did a 180. While walking to another bar, out of nowhere, he started shouting and being snarky at me. He kept saying, “You women hate short guys like us”.


He was short, yes. But I hadn’t said anything to him about it. I didn’t draw any attention to something that didn’t seem to matter to me. And I was ON the date! I chose to keep going around with him knowing he was that tall. I thought we were having fun. It’s not like he tried anything on me and I turned him down.

To this day I am still baffled as to what made him snap. Was he expecting me to randomly throw myself at him at some point? Was I supposed to try to cut the date short and insist on jumping on him right then and there, or what??

After his trash talk, I just stood there gobsmacked. I was the woman who gave him a chance. But then I tearfully said, “I thought we were having fun, but thanks for making me feel like garbage” and I literally ran away, leaving him standing in the street. I blocked him like the madman he was.

I feel bad for him, but not enough to accept mistreatment when I did nothing to deserve it. Ask me why I only dated tall, confident men after that.

Black couple arguing outsideKeira Burton , Pexels

35. You Thought Wrong

There was tons of flirting leading up to the date. On the actual date, there was more flirting, arm touching and hand holding. We even talked of doing a movie night sleepover with extra cuddles.

After I walked my date to her car, I went to kiss her. She got nervous so I pulled back before I got too close. She said, “Oh sorry. I just uh…” then paused for a good five to ten seconds. Meanwhile, I was left standing in a little bit of confusion. She then continued “…I thought you were gay!” 

I immediately asked about all the flirting and she said, “Yeah, I don’t know—I usually don’t do that with my gay friends. I’m sorry”.

I was so confused that I just mumbled, “Okay, have a good one” rather than try and figure out what the issue was. In her defense, it’s not incredulous for me to come off as gay, but it also just didn’t correlate with anything that happened before.

Woman is talking to a man wearing black leather jacket standing next to a car.RDNE Stock project ,Pexels

36. Stakes Were Too High

Our online conversations were phenomenal and we connected instantly. On our first date, within fifteen minutes of being seated, she declared that in order for this to continue I needed to fully and permanently commit to her right then and there. 

When I asked what she meant, her next comment was totally unhinged. She said, "You will either agree to be mine forever and we will go back to my place and have passionate intimacy all night so I can get pregnant or we can call dinner off now and go home".

The night of passion sounded fun but the risk was way too high. I paid the check and left immediately.

Young man is seating on table with a girl and drinking red wine.Katerina Holmes, Pexels

37. The Truth Is—

We were out on our fifth dinner date when I decided to open up about my anxiety and tell him why it limited me in our relationship. He cut me off and loudly proclaimed, “Is that why you won’t be intimate with me—because of your ‘anxiety’?”

He then proceeded to leave me at the restaurant—when he was my ride.

Young woman is seating alone at restaurant with sad face.Beyzanur K. ,Pexels

38. Act Your Age

My date got squeamish that I had blonde stubble on my legs and because I mentioned the existence of menstruation. I forget the context in which I mentioned it, but it was apropos to the conversation. I literally just said the word, not like I was having a detailed discussion or anything.

Anyways, the odd thing was that he was a second year med student. So one would think that he wouldn’t have acted like a juvenile about basic human biology. It honestly was so weird and childish.

He’s 25 years old and says “ewww” on a date at the sight of a 2-day-old leg stubble. And he wants to be a doctor? Good luck with that.

Young bearded man is making disgusting face.wayhomestudio ,Freepik

39. Adios, Princess

When my date arrived, all was going well. She seemed nice and we started getting on. When the waiter came to take our order, she asked what their best cabernet was. She then made sure that he double checked that it was "the stuff from the top shelf".

The waiter just looked at my cheap clothes and said, “What we have on the menu is what we’ve got”. She just puffed and pouted for the rest of the date. After that, I made sure that we got separate bills. When I requested that, she nearly lost her marbles.

“You are a man. It’s your job as the man to pay for everything. If you are far too poor to pay for things then maybe we shouldn’t go out again!” My comeback was perfect. I just said, “I’m way ahead of you there”. I paid and left.

Young woman is arguing with a man seating at restaurant.Roman Kosolapov, Shutterstock

40. You’ve Got It All Wrong

I generally try to be courteous to people, so I often open doors for both men and women.

On our date, I opened a door for her and she absolutely laid into me. She thought that as a woman, I didn’t think that she could open her own door. I was a bit perplexed as I never saw it as anything other than being nice. I certainly appreciate it when others do it for me. 

Oh well, there was no second date.

Man in grey suit is opening door for woman in grey suit to enter and smiling.Dmytro Zinkevych, Shutterstock

41. You Couldn’t Wait To Tell Me

I took a girl on a date to our city's local zoo. During the winter, they decorate the entire place with Christmas lights. They have a light show and even a Ferris wheel. It really is a cute winter date idea.

Well, we were on the Ferris wheel looking down on all the cute lights and holding hands. I then asked if she was having a good time. She looked at me nervously and told me, “I’ve been talking to someone else. I told him about our date and he decided to beat you to it”.

Awkward. At least wait until the ride is over to tell me.

Couple is taking a selfie on cellphone against illuminated Ferris wheel.Depiction Images, Shutterstock

42. I Need A Breath Of Fresh Air

I was on a date where the guy showed up and had really bad breath. The date was going well, but it’s a huge turn off to meet someone for the first date and they couldn’t even be bothered to freshen up beforehand.

I mean, I would’ve have kissed him and maybe even more if it didn’t smell like he had been nibbling on little pieces of dung droppings before our first date.

A girl is looking at side and holding her nose.karlyukav, Freepik

43. An Ugly Moment I’d Like To Forget

This was in high school. She invited me to her house to have dinner with her family, whom I didn't know very well.

The conversation turned to names we thought were old-fashioned and ugly-sounding. We all threw out a few like Gertrude, Bertha, and Eugene. Then I said the worst thing possible. I said something like, "At least that one's not as bad as Deborah!" I used my ugly voice and everything.

Her mom's name is Deborah. Her grandmother was also at the table with us. But hey, we've been married for almost seven years!

Man is talking at family dinner.Askar Abayev , Pexels

44. Funny Mix-Up

My aunt set me up on a date. I am half Asian and half European. So when I visited my family in Asia, they wanted me to date and probably marry this girl because she comes from a rich family.

On the date, we met at a restaurant. She brought her brother. He brought his girlfriend. I went there with a cousin. He thought it was hilarious. We all introduced ourselves to each other, but because the restaurant was loud and they’re mumbling, I didn’t manage to understand their names. 

I decided not to ask them all for their names again, fearing I’d come across as rude. So I talked to my date and she was well-educated and good-looking as well. I started to think—Hey, this wasn't a bad idea. I actually liked her and we seemed to be on the same wavelength. 

I started to flirt with her and she seemed to like it. Then suddenly, the brother said something and he and my date both got up to leave without saying anything else. I was totally confused. It turns out I was flirting with the brother’s girlfriend the whole time. 

I never even looked at the girl I was supposed to date except when we first introduced each other.

Asian couple are having a lunch.cottonbro studio , Pexels

45. In Your Dreams

We just went out as friends, so it technically wasn't a date but it functioned as one. It was with a girl I worked with. I'd been interested in her for a while but we were just friends and that was fine. Still, we hung out a lot and eventually one night, we went out for drinks after work. 

Things started to escalate from there. Fast forward to later that night, we were both asleep at her place. Now, I hadn't been sleeping well all that week, partially because of her dragging me out with her. And when I'm sleep deprived, I have very strange dreams and am prone to sleepwalking/talking.

In my dream I was walking down this tunnel—like a metro tunnel. I saw this girl on the ground crying. She had no clothes on. I asked her what was wrong and she lunged at me. She was a zombie or something. She wrapped her cadaver-like arms around me. 

I managed to throw her off and started yelling. That's what I saw in my dream and I was fighting for my life. What really happened was so embarrassing. What actually happened outside of the dream was her trying to cuddle with me. I responded by freaking out and literally throwing her out of the bed. 

She screamed and that partially woke me up, but I was still mostly in the dream. She asked me what was wrong and I just started yelling things out—”Who are you? Where are your clothes? Get away from me!” I woke up fully as she stormed out of the room. 

She thought I was trying to be an idiot, I suppose. I felt awful. I thought I blew it. Once I explained what happened, she thought it was hilarious and came back to bed. She still bugs me a lot for it, though.

Young couple are seating on bed in bedroom.Kampus Production , Pexels

46. Talk About Weird

A girl and I are on a first date. We have a nice dinner, and there's definitely some chemistry going on. We decided to go see a movie, but had just missed the one we wanted to see. Our other options were Scream and some Sylvester Stallone action movie. We opted for Scream.

At this cinema, there were a LOT of people talking back to the screen during the movie. It got quite infectious and eventually it got to the point where I was doing it too. I started yelling out, "DON'T ANSWER THE PHONE!!!!" along with half the people in the audience.

Anyway, after the movie ended, she barely said a word to me and I never heard from her again. Either she knew I was too good to be real and couldn’t trust herself around me, or she got drier than the Sahara once I was labeled the kind of person who talks back to movie screens.

Couple is watching a movie at cinema.Pavel Danilyuk , Pexels

47. A Narrow Escape

I finally took a girl out on a date who was flirting with me for over a month. Throughout most of the evening, she was really into me. She kept hanging on me and whatnot. So I thought, “cool, I’ve found myself a great girl to continue with”. 

Then just before the end of the date, her boyfriend showed up—like what in the world! We had been playing pool for at least four hours at the time. The boyfriend took over so I just slipped over to the counter and requested for my ID back and left

Three hours later, she called me. She started ripping into me for messing up the date. My only answer to her was, “You have a boyfriend. What date were we on?” Apparently, the total cost of the pool table was over 200 bucks because her boyfriend tore the felt.

Talk about a close call.

Woman is watching a man playing snooker.Ketut Subiyanto ,Pexels

48. First And Last Date

I was on a first date with a smart, beautiful, successful woman who I’d met online. We spent several weeks chatting and building a great rapport.

The date was going very well. We had instant romantic chemistry, a great deal in common and were really enjoying a great evening together. After dinner we proceeded to a nice upscale lounge and continued laughing, drinking, flirting and chatting about our lives for a couple more hours.

The conversation eventually shifted to us both being single parents of daughters around the same age—which is something we had already discussed online, so naturally she decided to show me a picture of her child and I in turn did the same. But then it all took a huge turn.

Suddenly, she looks at my daughter’s photo, tells me her name—which I hadn’t revealed—and proceeded to tell me that our daughters already knew each other. Even though they lived over an hour away, they knew each other. On top of that, she actually also knew my ex through a mutual friend. 

At the time, my ex and I were not on good terms. So, that date quickly shifted from being what was seemingly a great first date, to also being our last. We never saw each other again.

Couple are drinking coffee and looking at cell phone.gpointstudio , Freepik

49. Oops, Botched That One

We ordered a small snack for our coffee date. As it's arriving at the table, he pulls out his Nokia phone. Trying to make a lighthearted joke, I say "MAN, that has got to be the oldest phone I've seen in a while".

I really dug it in, trying to break that friendly wall. I'd screwed myself so badly. It turns out it's not a Nokia phone. It was his insulin pump.

Woman is making a surprised face.Andrea Piacquadio, Pexels

Sources: Reddit,

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