38 People Share The Biggest “WTF?!” Moment In Their Dating History

There's Something About Mary / Amazon.com
There’s Something About Mary / Amazon.com
Found on AskReddit.

1. A really weird way to trap your date…

Went out with a girl for a first date. She took me to a Kumdo lesson, which is a Korean sword fighting sport. I thought that was cool, but it was an advanced class and I made somewhat of a fool of myself but all in good fun. Anyway it turned out that she was bringing me there because she wanted me to be part of a documentary about foreigners in Korea. So my looking like a fool was broadcast nationwide. We then visited the grandmaster’s house for makeolli and the film crew started interviewing me. They were basically focusing on my relationship with the girl I was going out with. They didn’t seem to understand it was a first date. So here I am trying to answer awkward questions without embarrassing both of us on national television.

2. When a first date is a potential serial killer…

There was a guy who had been asking me to hang out for a while and I finally said yes, he wanted to hang out at his house with his roommates so I went. He took me into the basement where there was a dirty mattress on the floor and nothing else. I ran. To this day I have no idea what it was about but I ran and never told anyone about it until now.

3. Sometimes even the sweetest guys are still assholes.

When I was a teenager I worked at a retail store in the mall and a guy who worked a few stores down would always come in and talk to me. He was super sweet and genuine and would randomly take me to lunch/bring me coffee and the like. It was nice to just have someone to talk to and who seemed genuinely interested in me and what I had to say. He asked me on a date a few times and I always declined. I don’t like the idea of dating someone who I work with/work next to (just in case it goes sour) After a month or two I finally agree to go on a date with him, because good guys are hard to find! I couldn’t just let him pass by. He picks me up at my house and on our way to dinner we get into a car accident. The driver’s side was t-boned pretty badly and we ended up having to go to the hospital where he contacted his roommate….. who then contacted my date’s girlfriend.

4. A pretty accurate dating red flag? The date is at Friday’s.

After my freshman year of college I met a guy on OK Cupid and we went to get dinner at Friday’s as our first date. Offered to give me a ride, but I said no.

He was a couple years older, well dressed and started talking about how he’d started his own business after college and it was going well. Good for him! Bragging a bit but hey that’s an accomplishment.

So after we order he says “Let’s play a game. We’ll each take out our wallets and compare what’s in them.” Wasn’t a joke, literally started showing me his credit cards and bragging about the high limits, ending with “Clearly you can’t afford to pay for this dinner, but don’t worry I can cover you.” I was pissed and protested but he wouldn’t take no for an answer.

So as we leave he says he wants to show me his car. Unfortunately it was before mine in the lot so I had to walk by it. It was a white, windowless serial killer van. He begged me to fuck him in it, right there in the Friday’s parking lot.
I was pretty glad I drove separately.

5. Hard to believe that this wasn’t a prank.

I went on a date with a guy that I met online. He told me to dress nice and that he was going to take me out for dinner. He took me to Subway, ordered a foot long teriyaki chicken sub. He looked at me and said, “I hope you like teriyaki chicken.” We shared the sub in his car.

Safe to say there was no second date.

6. If you’re pregnant, you should probably refrain from blind dates.

Went to pick a girl up at her house after meeting on a dating website. She seemed significantly larger than her photo, but only in the lower abdominal region. This is when I realized that she had failed to mention that she was pregnant.

7. When two people are on two ENTIRELY SEPARATE pages.

I met this cute girl in college. I asked her out a couple times, she was really into me (numerous occasions we sat in a coffee shop for 6-7-8 hours talking the night away), but couldn’t do anything about it as she was seeing someone else. Ok fair enough. I’m a little persistent, we hang out on an off, 6 months later after she and her significant other break up (or so I was told), we start seeing each other.

Fast forward 8 months and she’s at my place 6-7 days a week, has taken over half my condo with her stuff, we commute to work together, I’m having supper with her parents, always hanging out with her sisters and their boyfriends, she’s always over at my parents, things are going really well. I was crazy about her. Part of the family and all that good stuff.

About a week before Xmas she sits me down and basically says that she never really broke up with her boyfriend, he was just out west. He was coming home and we were over. She was just seeing me “on the side” and quite frankly didn’t understand why I wasn’t seeing someone else at the same time – seeing how “we weren’t all that serious”. Excuse me what?!

8. A Jewish girl is dragged on a date to church…

I had a guy take me to a Beer n’ Christ thing. He was uber-Catholic and thought I could benefit from letting Christ into my cold, cold, cold Jewish heart. So I go. I’m open minded. I’m only half-Jewish and have always been interested in other religions. It was going “okay” until the Priest (the speaker of the night) told us a hypothetical tale of our brother who is paralyzed. We have the ability to cure him with stem cells – he will walk as soon as the “transaction” is complete.

“How many of you here would purchase these stem cells and allow your brother to walk again?”

My hand shoots up. I look around the room……nothing. No hands. I then notice everybody staring at me. Including my date and the priest. I was blessed out like nobody’s business and was told I was an embarrassment to my date.

Good Times.

9. Talk about some great post-sex conversation!

After I made him dinner, did the dishes, and we had amazing sex, he rolled over mid-cuddles to tell me all about his ex-girlfriend, how I had no desirable girlfriend-esque traits, and that the only reason he liked me was because I liked him. I boosted his confidence.

This was after a month of seeing each other.

10. Sounds less like a date, and more like he just needed company while trying to convert to Scientology.

On my first date with a guy off an Internet dating site, he took us to the Scientology museum in London. I thought “Hmmm, original, easy to find things to talk about/ laugh at the craziness of, this could be fun.”

Then he proceeded to read every, single, piece of writing on every, single exhibit, ask the attendant very probing questions about how one goes about joining scientology etc. etc. and sounding slightly too interested to just be intrigued about a religion. Also he was visibly sweating.

Once we were done there we went for a glass of wine and he told me he used to shoot heroin.

I was out of there like a shot.

11. Lesson learned: stay away from guys with tempers.

When I was young and stupid I dated a guy with a temper. He would get mad about something stupid like saying goodbye too quickly on the phone, pick a fight and we’d break up. He would call a day or two later and we would make up. After a few months I had figured out the cycle and I was fed up. So, when he picked a fight as usual I ended it and then didn’t take him back. While we were dating I had become close with his sisters and his mom loved me. We had scheduled a girls lunch and his sister begged me to go. I finally said yes and went. Everything was fine and I had a great time. The whole lunch was probably 2 hours long. At the end I walked to their car with them and the mom grabbed me and said, “Hear him!” Out of the car comes her son (WTF!) who was trying to explain to me why we should be together. I just walked past him to my car as he ran after me. He ended up picking a fight with me because “it was my fault we broke up and I didn’t even call him so he could fix it.” Then he threw rocks at my car as I drove away. I wish I had a picture of what my face looked like when he came out of that car. I never spoke to him again and never accepted another invitation from his family.

12. Lady, you’re bringing me down!

There’s been a few but the absolute worst was the woman who turned up to the pub with literally no money, expecting me to buy her drinks and dinner. I wouldn’t have minded if she’d have told me beforehand but this was completely out of the blue.

So anyway, we sat there making awkward conversation, or at least I tried to start a conversation, told her about my life, asked her questions. She was too busy texting and phoning her friends to really take notice.

So eventually we did get talking, and then out of nowhere, she told me that she killed her dog. Not accidentally either. I just upped and left and avoided all contact. That was 2 years ago.

13. Yup, this girl is heartless.

A girl I had just met asked me out, she wanted to take me to dinner. We end up at this little Italian place, she says she knows someone that works there. When our waiter arrives, he appears visibly shaken, stuttering. She introduces me to him, this is her friend she mentioned before. I can see it right away, this guy has a thing for her, and here she is introducing him to her date. She then bugs him for special orders and asks if we can get our meals free. He really seems upset, but gives her the “anything for you” look and agrees, I decline and pay for my own meal. I felt really bad for this guy, I could just see his torment at watching this girl date someone else. She was very attractive and very friendly, I assumed he just got friendzoned. I hung out with her a few more times, but backed off of the romantic part. Then I found out that the guy from the restaurant was her ex-boyfriend, who she had just dumped a few days before and had been dating since high school (this was 2-3 years after I graduated).

14. Sounds like this girl needs help.

Met a girl on Okcupid. I take her out to dinner she seems a little odd but overall nice and the conversation is going well. We both like video games so I invite her over to my place after dinner for some Xbox action. She proceeds to drink all my liquor and take all my left over hydrocodone from a work injury I had suffered a few months prior. She starts unplugging all my shit and calling me names like “Brian” and “Todd” and saying how she doesn’t like it when people hit her. I tell her I’m taking her home and have to physically drag her to my car with her kicking and screaming the whole way there. She then try to get out of my car while we are on the highway but thankfully I had the sense to lock the doors and she was too fucked up to realize it. She gets pissed and starts hitting me while I’m driving on the highway. I finally get her home get her through her front door and leave. On my way back to my car her fucking iPhone hits me in the back of the head. I drive home bleeding from my head. She calls me the next day from a number I don’t recognize asking how our date went and if I knew where her phone was. I laugh and hang up.

15. Only after two years did she realize how TWISTED THIS GUY ACTUALLY IS.

Ok so I had been seeing this guy for about 2 years, we lived together and I knew he was a bit of a pervert, but essentially harmless and adorable. So we went out to dinner one night and we got onto the topic of incest (ya, I don’t know how) and we ended up in a debate over the moral and psychological implications of incest. It took me about 40 minutes to finally convince him that parent to child incest was damaging to the child, but he refused to concede any point about sibling incest damaging the family dynamic (that and he just keep talking about how “hot” it was). So I asked him flat out “Ok so if you and I had children and they wanted a sexual relationship, you would not discourage that in any way??” He said nope, and said he’d encourage it if he could…. “well that just instantly assured me that you and I will never be having children.”

Honestly, anything I felt for this kid just fizzled out in that instant. I never let him touch me again.

16. True love, people…

A guy I was totally into moved pretty far away. We were interested in each other though, spoke a lot and eventually he decided to visit me for a weekend. I imagined romantic things happening. He wanted to go wallpaper shopping.

And so it was that our first ‘date’ was in the home furnishings department of John Lewis. He got lots of very ugly samples.

Then we went to Habitat where he looked at lamps and said the word “rimming” very loudly.

Within five years we were married.

17. Tried to woo her, scratched her eye instead.

Here is a story of my worst date ever. I am 16 years old dating an 18 year old girl. I really, really like this girl so of course I was super nervous. It was my first date ever in my whole life. I took her out to eat, then we went to see the 2nd Mummy movie. (It was terrible btw) Well everything was going great, I even had my arm around her and all that jazz. During the pigmy chase scene one of those dudes popped up and made me jump. My arm was still around her and somehow my finger went straight in her eye. I had scratched this poor girls eye. She then had to go to the ER, and then had to wear an eye patch for a few weeks. So the first date I ever went on, I turned the girl into a fucking pirate. Believe it or not she still went out with me a few times after that, but I think she felt bad for me. There is my dating horror story. Cheers.

18. Just before we have sex, a couple things:

I dated this girl for a few weeks. She wanted to take it slow, I was fine with this… One night things get heated. She was teasing me really bad. So she then says “Will you wait until we get married to have sex? Also, you need to join my Christian church and become a dedicated member of the community. Oh and I don’t want any alcohol in our relationship, you need to stop drinking”…. My immediate reply is, “I don’t think we can see each other.”

19. A discouraging experience after an already-discouraging breakup.

Break up with boyfriend. Trying to recover from broken heart. Decide to buck up and go out on a date. Start texting and chatting with this guy. Seems a little strange but I don’t mind. “What is the worst that could happen”” I tell myself. He comes to get me. Seems a bit wired. I’ve planned an evening of tea and movies. He says he rather go to this party. I am very polite and I’m trying to be opened minded so I say yes. Get into his car. Funky smell. Pulls out bag of pills while driving. Explains to me that he makes his own version of ecstasy. Tells me if I don’t want to try that he has other things. See collection of drugs in his car. Go to party then an after party. Feel trapped. After party everyone is getting naked and snorting Adderall. Feeling really anxious. Want to leave. Guy offers me weed. Get high in corner by myself. Drops me off later asks if he can have any of my medication. Awkwardly say no. Give up on love.

20. Yeah, I’d say he deserves to be in jail for life.

The last person I dated before my fiancé was certifiably insane. He didn’t believe I was at my parents, so he kicked down my front door to see if I was there. I wasn’t, so he just sat on my bed eating my fucking food until I got home, because that’s completely normal behavior. He went through my laptop and found a picture of another man on it, so he threw the laptop at my face, then Hulked out and broke it with his bare hands. The photo was of my cousin with Down Syndrome. I got a new car, he keyed it the same night. He didn’t want me to go home one night so he injected me with 70cc of insulin. The day I left him, he showed up to the hospital I was at (as a patient due to the insulin incident,) and choked and beat me. I had to have reconstructive surgery on my face. The whole time he was yelling that he was beating me so I couldn’t make anymore money (I model on the side,) and I’d have to move in with him and his mom. He’s now serving 30 years for domestic battery, theft of controlled medication, attempted murder, kidnapping, grand theft, vandalism, and unlawful imprisonment.

21. I guess it’s hard to be with a girl who is blatantly rude to other guys in front of him?

I went by a friend’s house and met up with this girl that lived in the same building as him. She was heavy into me, rubbing all up on me. She asked if I wanted to head to the bar, and I told her I had no money. She said she would get me drinks, so off we went.

At the bar, she was still getting all over me. I asked her about that drink and she said she would be right back. I watched her walk around the bar to some guys with a pitcher of beer. She teased and flirted with them and asked for a drink off the pitcher. They gave her one and she immediately walked back to me and handed me the drink, while the guys watched her.

I walked right back over to the guys, who were visibly pissed, handed them the drink and said, “sorry, I hardly know this chick, and I didn’t ask her to do that.” I left her at the bar.

22. This just sounds more weird than anything else.

Met this German guy at a university bar one night and he seemed really into me, so he asks for my number and said he wanted to take me out on a date. Fast forward a couple of days and he calls and asks me to go for dinner that night. I didn’t know him very well at all but I figured I might as well go for it just to see what he was like. He picks me up and says we’re going to go to one of the most expensive restaurant in the city, and when I start to object and say I can’t afford it he just says “babe you’re worth it”. I’m a little caught off guard at this point, then he says we’re going to make a stop first before we go to the restaurant. He takes me to the mall and we both get out and go in. He grabs my arm and makes a beeline for this really fancy leather goods store. I’m just standing there thinking what the fuck is going on? When he says “ArcadeLiar pick out any purse you want.” I objected and said I didn’t need or want a new purse, but he looks at me and says “Your purse is falling apart. I don’t want to take you to the restaurant with a ratty old purse like that.” I just stared at him and then turned and walked away and got one of my friends to pick me up.

23. When a date turns into a visit to the abortion clinic for his last conquest.

College days. Guy in my Econ class asked me out for lunch. Yes good. Says his car is in the shop; can I drive? Okay. I pick him up, and on the way, he asks if we can stop at a place so he can take care of something “real quick”. Yes but less good. We arrive at the specified destination, an abortion clinic where his six-weeks-previous one night stand-er is waiting to be treated. “It’s OK if you want to come in,” he assured me. “She could probably use some girl support, if you know what I mean.” (Meaningful eyebrow-furrowing here.) He didn’t even have the car door all the way shut before I was escaping. For the rest of that semester in class, he flipped me off every chance he got. THAT part makes me laugh every time I think of it.

24. And this is why you never get your parents involved.

When I was a freshman in high school, I dated a guy for two weeks. My parents were really excited and wanted to meet him, so they took us (the whole family, me, and my boyfriend) to a Johnny Cash impersonator playing in our town’s theatre, and then to dinner at Shari’s.

The audience was almost entirely old people, and at the time it was so fucking awkward.

It’s still fucking awkward today.

Epilogue: We broke up after two weeks. A year later, I came out as a lesbian. He is studying fashion design in Italy, last time I checked.


Buddy of mine met a girl in my apartment parking lot then decided to go on a date with her. When he arrived at her apartment there where shit stains everywhere form her dogs… sure everyone with dogs has a couple, but this girl wouldn’t take her dogs out, so they just shat in the house normally. After they left, she suggested they go to a waffle house or some shit, in the worst area of town. After a slice of what I am sure was the worst pie in the fucking world, she asks him to take her somewhere, he follows her directions. Bam. Planned Parenthood. Girl gets a fucking abortion. During the date. After this, while she is explaining how she doesn’t know who the father is, she asks to go to petco; she buys a rat. They arrive back at her house and she replaces a dead rat out of her cage with the new one. She then explains she has to buy a new rat every other week or so because they die. My buddy was pretty sure she didn’t feed them. Jesus. Abortion Date. Beat that. Also, she left him voice mails every day for about two weeks. When he never returned her calls, she left a psycho-we-were-great-together-why-would-you-do-this-to-me message, and finally stopped calling him back.

26. Here’s what NOT to say to a recovering alcoholic:

I went on a first date with a guy who knew I was a recovering alcoholic and at the restaurant he hands me the beer menu and tells me to pick something out for him “since I’m obviously an expert.”

27. This guy SURE knows how to seduce women.

Met a dudebro on plenty of fish. Tried to leave at the end of the night while he was begging me to join him in the back seat for… whatever his intentions were. I said I was tired and wanted to go sleep since I had work the next day. He replied, “Well, what’s more important?”

Uh, my sleep schedule is more important you fucking clod, that’s for sure. Also, my boundaries are more important.

He had pillows back there, too. Ugh. Total creep.

28. Another reliable red flag: when movie night = watching porn.

On my first date the guy took me to his place to watch a movie. He wanted to watch porn. We ended up watching porn. I don’t know what was worse, him jacking off to the porn while I sat there uncomfortably or that I did not leave when he told me that we were going to watch porn for the “movie.”

29. Sounds like she got USED and ABUSED.

I went on a date with a cute girl I met online. (We’re both girls). She worked on Wall Street making a shit ton of money, and I was a grad student at the time. She chose the place– a very fancy restaurant in the nicest part of town, and ordered a $100 bottle of wine. When the check came, she batted her eyes at me and made no moves to get her wallet. I was just drunk enough not to start a fight and paid for it. But, seriously??

Then I figured I might as well get something out of it and went home with her to her fancyass high-rise apartment. We had sex– or, I should say, she let me go down on her and offered nothing in return. Then, at 4 am in the pouring rain, she kicks me out, saying she has an early morning.

I left my favorite ring at her place and she never returned it, either.

30. A date in which the crazy mom got involved.

9th grade. First date. He was an only child. His mom drives us to the movies. When we get back, his mom starts crying and saying he was going to be a big football star and I’m a golddigger just trying to capitalize on his success (mind you, he’s third string of the school’s ninth grade team). They had a family meeting. My sister arrived to pick me up. They wouldn’t let me leave the room until it was resolved.

31. For a first date, just please don’t invite your whole family, k?

I had been friends with this guy for a couple months, and one weekend at a party we kissed. He was a nice guy, but a terrible kisser. He asked me on a date to go to an art gallery and I thought that sounded really cool so I said yes. What he failed to mention was that his entire family would be there – parents, siblings, grandparents, etc. It was painfully awkward, to say the least. He invited me to have dinner with them and I made my excuses and left, and said I had plans that night as well. Later, he showed up uninvited and alone to the party I was at that night. Creeped me out.

32. Man, does he know what a girl likes to hear on a date!

I once went on a date with a guy who told me, while being seated at a restaurant, that there is nothing more disgusting than seeing a woman put food into her mouth. He said this with a facial expression of sincere disgust and went on to explain that his mother was terribly obese and embarrassing. Thankfully it was a first (and last) date. So I did what any self respecting girls would do. I ordered the most expensive seafood on the menu and didn’t touch it. I hate seafood. It was a rather boring hour hearing him talk about himself, never showing any interest in my life, and then getting irate when the bill came. Guys, FYI, this is an example of what NOT to do on a date.

33. Um, yeah. Don’t be surprised if the response is not positive!

A guy once told me he’d like to take me out for dinner by saying he’d “love to food-fuck [my] face hole.”

And no, we did NOT know each other well enough (had only spoken two or three times) for him to whip out a feeder fetish.

34. When your date is a klepto…

I was in high school and at a time in my life when I really wanted to get it on with the fair sex so to say. There was this female from my high school who seemed interesting and I asked her out on a date for Valentines Day. I was over the moon when she said yes. We went for a movie, did awkward hand holding and the usual first date stuff. Afterward, as we were getting ready to leave, she wanted to go for a quick visit to a gift shop. We went to a nice one nearby and I bought a few greeting cards etc while she just “browsed” around. When it came time to pay, I paid for my cards and was getting ready to leave. The cashier asked me if I wanted to buy anything else and I said no. Then he asked my date “Is there something you want to buy miss” Hmm.. Weird… She said no.. He asked again “are you sure”.. Girl “Yes I am sure”.. The cashier shouted “NOW” and 5 of the staff surrounded us like a scene from a cop movie. I was like WTF. The girl apparently was a kleptomaniac and had stuffed lots of gifts in her pant and bra. They had electronic surveillance and had caught it all on tape. The guy threatened to call the cops on the girl and told me I could leave as he could see I had no idea what was going on. I decided to help the girl out and ended up buying all the stuff she had stolen to get her out of getting busted and her parents finding out. Needless to say there was no second date.

35. This girl sounds awful.

There was a girl in my class that was really hot, but you could kind of tell that she really knew that. This should have warned me off, but I was thinking with my dick so I asked her out. She turned me down, but then called one Saturday night and said she changed her mind. This should have been my second warning, but again, dick. So I pick her up, and ask her where she wants to go, and she says Red Lobster. I tell her that I have a shellfish allergy and can’t really go there, and she responds, “Well just drop me back at my house then”. Once again, I relent. I end up eating plain fettucine alfredo, and the entire time she is incredibly rude to the wait staff. Halfway through dinner I decide that fuck this, it’s not worth the abuse, so I plan to take her home right after. When we get in the car, she DEMANDS that we go see a movie. Well, the nearest theater is a good 45 minute drive from our podunk college town, but I get to thinking about stuff you can do in the dark and once more, I make a bad decision. We drive all the way to the movie theater, and as I am parking the car, she says “You are really terrible at taking care of women, my boyfriend always drops me off at the front”. WTF?! BOYFRIEND? Why the hell are we on this date? So I apologize, drive the car up to the front and let her out. Then I just fucking drove home. The next week in class every girl was staring daggers at me for how I had “mistreated” her.

36. Persistence paid off!

In college, I had been avoiding a date with this guy I had met at a bar and drunkenly given my number to. One day he called me to ask what I was doing and I told him I was walking home from the library. He said, “Oh great, cause I’m outside your apartment. I want to take you to dinner.” Sure enough, he was there. Dumb founded, I stupidly got in the car. I was wearing jeans and t-shirt and noticed he was wearing a suit. Not a nice shirt and pants, a full on suit. So I immediately say I was going to go upstairs to change and he insists that it will be fine. We’re driving for a while and he won’t tell me where we were going. We pull into the mall parking lot. At this point I was assuming there was a gas station or something near by that we were stopping at. Nope. He parks and motions for me to get out. We walk in, him in his suit, me in my jeans to the mall food court. We got sbarro pizza and played games in the arcade. I didn’t see him again.

37. At least she got a great story out of it?

My VERY FIRST DATE EVER. I was 14 and I finally got asked out to the movies by a super cute guy from another school, and I was desperately grateful because I was such a nerd. I spent the whole week being giddy about finally going on a REAL DATE like a REAL PERSON and imagining how nice it would be to do something romantic for a change.

Aaaaaand he shows up at my front door in lingerie, high heels, a bra and full makeup.

He neglected to tell me he was taking me to The Rocky Horror Picture Show. At the time, I didn’t know what the hell that was, but lets just say when I pictured the cute boy picking me up for my firs ever big-girl-date, I was not expecting that. :/

His mom drove us. =_=

38. Dads often do know best.

My dad does not usually involve himself in my dating life, but I told him I was going out with one guy and he told me he didn’t like him and I shouldn’t go. I thought that was strange because he’s usually pretty indifferent to who I date. So later the guy comes and knocks on my door, I open it and the first words that come out of his mouth are, “Oh, I thought you were going to wear something cute tonight.” Sometimes Father does know best. Thought Catalog Logo Mark

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Charlie Shaw

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