41 Men And Women Share The Most Insane Dates They’ve Ever Had To Suffer Through

28. …He’s Just My Brother

I’m a dude. I was about 16 at the time. My female cousin tried to hook me up with her “nice friend” whom I had shown interest in after meeting her at a family gathering. We text and talk on the phone for a couple weeks. Later we agreed to meet at the mall. We get to the mall and the girl shows up with another guy, who is her boyfriend. Yes, she introduces him as such and all that. Apparently, he was her ride to the mall. My cousin didn’t think this was odd. I was highly annoyed the whole time because the girl is really fine.

We walk around the mall, the girl, my cousin, and myself. The boyfriend waits in the car. The girl tries to get me to buy her stuff in the mall, I lie and say, “Oh, I don’t have it like that right now.” She tries to hold my hand, asks me to get her something at the food court, the latter I give in and do. I tell my cousin I’m ready to leave. And the girl goes, “You’re cute. And sweet. You should totally be my guy.” I was dumbfounded, “Don’t you already have a bf?” “I could have two! Besides, he’s just my brother. I don’t have to commit to him.” My jaw drops, and I just tell her no thank you, and leave quickly. My cousin asks what’s wrong, STILL no seeing the problem with her friend’s relationship status. I’m still weirded out by that to this day.


29. An Arranged Date Goes Terribly Wrong

I have so many, I could write a book. Let’s start with the first bad/weird date I’ve ever been on-

Got setup with the son of one of my mother’s friends from our Synagogue. He picks me up at my parent’s house (we were 16-17). Not even 10 minutes into the date, we were literally driving to a restaurant, he point blank asked me if I would rather give him head now or after dinner. To which I replied- excuse me? Perhaps I misheard him? And he smiled and replied slowly as if I was hard of hearing – are you going to suck my dick or what? At that point, I yelled at him to go fuck himself and pull over. I kept yelling pull over as loud as I could. He started to freak out but pulled over. I got out of the car and started walking home.

He followed next to me for a few blocks with the window rolled down imploring me not to tell his mom or my mom. I ignored him and refused to respond so he got frustrated called me an ugly skank and drove off. I got home (about an hour later as I walked all the way home- this was before cell phones) and told my mom what happened and she was justifiably mortified. She, in turn, calls his mother and tells her exactly what happened. The guy’s mom didn’t take it well and tried to put the blame on me, that “she asked for it.” Needless to say, my mom never talked to her again.

Other bad dates I’ve had include- a magician, a Craigslist personal ad, a nurse looking for drugs, a married man and so much more.


30. Happy Feet

This was in high school, some girl from our rival school and I met, hit it off. She really wanted to see the movie “Happy Feet”, the dancing penguin shit. Decide to take her, I like penguins anyways. I swear about half way through the movie she leans over to me and says, “Oh I get it, they’re dancing!”. I thought she was trying to be cute, but she was goddamn serious. This movie was her idea, I figured she knew. The fucking penguins were dancing for at least an hour before she said this to me. We lasted another week.


31. A Lot Of Assumptions Were Made

Met a girl online, decided that we should meet for a date. (I’m female BTW – this sort of matters). I arrived in a strange town that I didn’t know so I relied on her to show me around. She took me to a youth LGBT group, I thought we were staying, didn’t mind – it’s a bit odd but I was newly “out”.

Turns out it was just a chance for this girl to show off that she did, in fact, have a date (they didn’t believe her apparently) and I existed. It was really awkward. When the youth group leader came in, she stood up, grabbed my hand and said “later bitches” and we walked out.

Went to a bar for a drink, and then on for some food. It wasn’t going well, she was very odd, but I was new to all this, and in a town I didn’t know. Once we’d eaten she said, “oh I just need to see a mate who’s staying at xyz hotel” – fine, went to see this friend. Oh no. She’d booked a hotel room for us for the night! Yeah – I left pretty quickly after that. I may have been inexperienced, but I wasn’t about to be tricked into a night in a rough hotel with an odd little lesbian. No thank you.


32. A Glitch In The Matrix

It was my second date with this guy, and he said the exact same things that he said on the first date. Word-for-word. The same stories, the same “random thoughts,” the same questions… It freaked me out so much that at first I played along and answered in the exact same way, as though we were both following some weird, script. Eventually, I tried to break the mold and ask him new things, but he would just bring it back around to the same topics as last time. It was like I was in a computer program and there was a glitch. Still freaks me out to think of it.


33. Date Becomes Road Trip Becomes Torture Chamber On Four Wheels

I started talking to a girl I came across on a dating site. We made plans to meet about 1 week after we began talking. I ended up canceling the plans a few hours before we were supposed to meet. As I had something come up. Told her I was available the following day as we do not live in the same city. A few hours later she responded. Asked me if I wanted to take a road trip to another city a few hours west from where I’m located. She just wanted a co-pilot to keep her company. I agreed although, partially because I felt bad for changing plans at last minute the previous day.

I was skeptical, I’ve never just taken a random road trip with some girl that I haven’t met before. She picks me up in the morning. Not too awkward at first, easy conversation for the most part. Within 10 minutes of being on the road, she needs to piss.. but can’t wait for next gas station. She abruptly pulls over on side of highway and does her business. Ok, I’m thinking whatever you gotta go, you gotta go…right? The place we were traveling too is about 200km from where I lived. Let’s just say we had to make another 5 stops, 2 more on Highway and 3 gas stations before we arrived at our destination. Yes, I started to count after the 3rd stop. Anyways I’m definitely thinking this girl has some kind of std or issues. That’s a lot of piss breaks in such a short amount of time.

Okay, so I was told she needed to pick a few things up in ***** city. So it wasn’t just things it was her 74-year-old Grandmother! whom I would shortly be meeting for lunch, along with a few other members of her family. I said to her “wtf, you’re kidding right” …well she wasn’t. Well ffs, at this point I did not have much of a choice considering she is my ride back home…

Long story short, it was awkward as fuck. Her aunt a cousin and some family friend with her grandma. it was like a fricken family reunion. I felt like I was in some kind of dark comedy show, and I had to improvise bullshit. Anyways made it back home after 4 more pee breaks, and having to pretend/lie to her grandmother about actually knowing anything about this girl. Ya, I didn’t talk to her again. How is that for awkward?


34. A Total Shitshow At The Tapas Place

Meet a guy online. He asks me to dinner at a tapas place, I agree because I’m bored and he seems nice enough; we’d been texting for a couple weeks and it seemed chill. I get there and he’s late to meet me. Looks nothing like his profile (about 100 lbs heavier, bad skin, and is just dressed really sloppily) but I told myself not to be shallow. We are looking over the menu (which was fantastic btw) and I suggest a few things I’d like to eat and he begins saying he doesn’t eat sweet potatoes, aioli, capers, salmon, radish, arugula, kale, balsamic vinegar, etc.–basically all ingredients except for bread, meat, and cheese–and that he won’t eat any food if that’s what I order. I tell him to get what he wants then and I’ll get something for myself. We get our food and he is the messiest eater I’ve seen in my life, getting crumbs and food bits all over his shirt and the whole table and it was just painful to watch.

He also kept insisting I try his food, but I’m pescatarian and lactose intolerant so I declined, at which he began berating me and my food choices and being a “picky eater”. They clear our table for dessert and he then gets down on one knee and tries to give me a promise ring because he “felt a special bond with me and wanted to pledge his life to me” after having met online a few weeks before. Yeah, no thanks. Politely as I could, I declined, to which he started calling me expletives in the middle of the restaurant and then ugly crying and stormed out. So I had to pay for the terrible date HE asked ME on because I didn’t want to accept a pre-engagement ring. TL;DR guy I met online turns out to be really odd and throws a hissy fit when I refuse to wear a promise ring he bought


35. An UnBEARable Divide

It’s 2001, so VHS & chill at this girl’s dorm room.

My first time over there, and there is this giant bear on the bed. Like, got the softball in the milk jug at the carnival first try tier bear. It occupies 50% of the surface area.

I say “whoa, how’d you score that bear?”

Her: “I don’t know…”

Me: “Wot?”

Her: “I don’t know”

A few minutes go by.

Me: “You don’t know?”

Her: “Yeah.”

Me: “Ok, look. It’s ok if it’s from an ex. I don’t care if you stole it. I’ll believe almost anything you tell me at this point. But there is no way in hell you’re going to tell me you don’t know where that giant bear is from. I had a stuffed dinosaur 1/4 that size that I got when I was 6 and I could tell you every detail about how I got it.”

Her: “Well good for you. But I don’t know how I got it. Are you going to be able to let this go?”

Me: (looks at bear, bear stares back, eyes full of secrets) “I don’t think I can” (walk out).


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