What's your most awkward dating experience?

There was a guy in my university classes (he was in 2 of the same classes as me), and he asked me on a date after some time in the school quarter. I said, "Sure," and he told me that he would take me on a ride on his motorcycle. The day of the date, we ended up riding along with his friend and his girlfriend; I thought, "Well, it's a double date, kinda wish he told me." But it didn't really matter much, so I let it slide. We ended up driving up around 1-2 hours up in the mountain side, which got me EXTREMELY nauseous (I also wished he told me where we were driving up to). We were driving uphill, I was clinging onto him from the back, and the helmet I wore didn't bring in much air, so the whole time, I was incredibly dizzy. After we parked on the side of mountain, we took a breather and chatted for a bit. One thing that bothered me about him was that he kept saying, "Oooh, I bet this is the best date you've been on," and "No one's ever taken you out on a motorcycle ride, huh?" After some time, we decided to head back down to the city to go to a restaurant. We couldn't leave because there were police tape all over the mountain side. Apparently, someone drove over the mountain side down the cliff in his truck, and they had to call in helicopters to retrieve the wounded person. After waiting a few hours, we were allowed to go back down. I was looking at the scenery while he was driving (the city is right next to the beach). All of a sudden, he started speeding up his bike to try to impress me, and next thing we know, we crash onto the side of the mountain hill. (It wasn't serious, but he did crash the handle on his balls, which he cringed in pain for a good time). At the end of the date, he still said, "Hey babe, bet'cha this is one good date you'll be telling your friends about, huh?" I laughed nervously and headed back into my apartment, and I just shook my head. tl;dr - Went out with a motorcycle-riding tool who crashed us on the side of the hill. The police had to retrieve a wounded person who drove his truck down the mountainside.

Well, at least you both felt the pain after it(Although I can't say the same kind of pain)... For me? None, not one, been busy ever since... Well... Can't remember when, but been a slave to work ever since, and being in the middle of nowhere didn't help much either, but over time I didn't need much social interaction, which gave me more time for either work or training, so yes, I might have a small case of hikikomori, but just the social part, when I need to work I work harder than anyone else, which apparently STILL isn't enough...

took a girl to dinner for her birthday... and i let one go right after cranking up the car... i don't know if i was just nervous or what but it was the worst date ever. we dated for 3 months after though

Hmm most akward date I've been to? How about the thing before the DATE. A girl tells me a friend of hers likes me right? Well for whatever reason she then tells me I should go on a date and possibly date her. The issue was she was an art student of mine (she's around my age) no i'm not a professor I just teach randomly. Anyway, this friend then confesses her love for her friend but she is scared of telling her how she feels. So now I feel bad about this whole entire mess because I sorta liked her too. lol So I didn't ask her on a date due to pity.

@ cielle http://i59.photobucket.com/albums/g308/Foowee/motorcycles.jpg Sry about the date ... but he was right about one thing ... you did tell the story to others.

Oh I have one I picked this girl I have been talking for a while. She seems nice and all at first but as soon as we lower each other guard she started talking a out how sexualy liberal she was and how she like to get done and such it killed all the spark there was or I had so I just made an excuse since her thing is to have sex on every first date so at that point I was like http://weknowmemes.com/generator/uploads/generated/g1327739101833967301.jpg

Only one that I can say falls into this was when I went out with the friend of my own friends sister. She was funny, good looking and could beat most of my male friends at Halo which always caused the word "rematch" to pop out which was fun. Upon date which we agreed to go to a local diner nothing fancy or formal, and then a movie. 30 minutes before time agreed to meet up, she calls me telling me she was having car troubles. I ask her if she would like for me to pick her up and immediatly she reply was "no need I can get a ride from one of my friends". Which I didn't have trouble with. She arrives at the meeting place and person dropping her off was her exbf ... I still smiled got her out of car openened the door but inside my head I was going (wtf?) Guy gets out of car looking tough and says "you better treat her right or you will be dealing with me" ... (wtf moment #2) .. I already had a bad feeling but at this point in time I didn't really care about the "tough guy" She of course tells him to stop joking around and what not. (He was serious abt trying to be threatening that's for sure) We ate at the diner no problems and then in middle of the movie she starts getting texts from this guy asking her when he should pick her up and things like that. I told her I didn't mind dropping her off so she should choose with whom she should want to leave with ... since first date and it was friends friend sort of thing. Now here comes the real fun part. As I am dropping her off I start backing up and tough guy ex bf arrives with 2 friends blocking my exit. DRAMA ... ACTION He starts telling her how much he misses her he loves her and that she could do better than a nerd that plays video games who's friends with blablabla... (how did he know I either played halo or was friends with her friends nerdy older bro? So one had a big mouth but meh I didn't care abt that) and she was good looking so she could of done different not better (can't do better than unique :p) All in all she tells him to get out of the way before her dad gets outside who happened to be a cop. Which I didn't know, and he kept his work friends keeping an eye on her during the entire date ... gota hand it to the old man I never hada clue. Well ... thug wannabe comes towards my car with his 2 buddies. With your classical tthreats from "never want to see you again" to "I will kill you". I just couldnt help but respond "sure buddy now can you move the car?" ... it seems me not being intimidated angered him for some oddball reason. His 2 friends start howling things like he will kill me and getting beaten up and all I could think was if all this crap was really necesary? Now. When the "tough guy" hits my car window with his fist you hear him go "ah" in the girliest way possible ... seems he hit with something he shouldn't the other 2 became mother hens moment "are you ok?" "Its not broken right? For some reason he thought he could punch the glass and break it like in movies .... After that the "dad" walks out and I see 3 headless chickens get into a car and run away. ... The "dad" walks up to my car asks me if the car is okay and that he would set those boys straight. He asks me before leaving if I was worried ... and I replied honestly. "Nope" He smiled and went back to his house. ... Yes this was the most exciting (oddball) date in my life.

@boundbyluck: LOL that's already a red flag when she's still that close with her ex-bf enough for him to drop her off at another date. Yah, that's true, I did end up telling other people about this motorcycle date... @wallace: yah that's a bit...weird, especially on a first date.

@cielle I am glad at least someone besides me found my experience amusing. And yes red flag, I should of had ended the date at the first (wtf moment). But I really didnt see him as a threat so I ignored him. But I wish I had listened to my own reasoning and avoided the drama. But hey I had to learn the lesson :)