Forlorn Lovers Discuss Their Most Awkward Dates.

A first date is like a job interview. Except, in my case at least, there's some chance a job interview ends with sex.

These are Quora's most awkward, cringeworthy, and hilarious tales of dates go wrong.

What's your most awkward date story? Let us know!

This was back in 2012, when I was a student at NYU.

I met this amazing girl on campus, a sophomore from Chicago. So, I asked her out.

Well, it turns out her sister was visiting her from Chicago the same weekend that we had our date planned.

Of course, she didn't mention anything about her sister, but she ended up bringing her along on the date that I had been so looking forward to.

The weird thing was that her sister was her identical twin.

I had no idea who was who all date long, and couldnt find a polite way to ask either.

She later told my friend she thought that I was more into her sister than her. It was very awkward. 

Was this a setup? I never found out.

Zack Jaffri

A guy once invited me to go see a movie. I agreed to let him pick it. He bought us tickets for 50 Shades of Grey (I didn't know anything about it before we went). Halfway through the movie, he turned to me and asked what positions I wanted to try afterward! There wasn't a second date.

Luana Matei

I signed up for a free dating site and started chatting to several guys. One of them seemed like a nice and decent person. After a week of talks, we set up a real life date.

When I first got into his car, he looked up at the sky and said, Do you find those clouds a bit weird? 

There were no clouds, only condensation trails from airplanes. I told him so. And he said, Exactly. Bit of an odd exchange, but I shrugged it off. 

To my surprise, the date he set up was not the usual movie or restaurant combo with drinking. Instead he took me to the riverside on a boat ride. It was sunny, and we chatted nonchalantly.

We were talking about building styles in the UK (I am a foreigner). I mentioned that my dad is a bricklayer, so I have seen many houses being built.

He said, I have built something too

I asked, What did you build?

It is very unique. You will see it one day, I hope. 

What is it, a bunker? I asked. And we both laughed. For different reasons. It was a bunker. He was a bunker guy.


What I noticed first was the pile of tiny plastic eyedroppers that was building up in front of us while we sat side by side at the bar.

I dont know why it took me so long to see this. And I dont know how he fit all those little bottles in his pants pocket - there must have been 100 of them, easily.

Im not kidding you - literally every 30 seconds or so, hed pull out two eyedroppers, and very swiftly tilt his head back and lubricate his eyeballs. He was so fast, and we were having such an engrossing discussion, that it took me at least a half hour to even realize what he was doing.

I politely asked for an explanation. He told me he had had eye surgery for a serious condition, and while that surgery saved his eyesight, he was left with the burden of watering his eyes approximately twice per minute.

Poor fellow. Being a contac lens wearer, I can certainly relate to the discomfort of dry eyes. It sucks.

But I was a bit taken aback by the fact that he seemed to expect the bartender to clean up the eyedroppers (I hope he left him a large tip for that). 

The poor bartender had to collect them all with a napkin each time the pile built up to roughly 2 inches in height. Id say there were about 4 piles over the course of the evening.

But thats not all.

Towards the end of the date, I pulled out my phone to see six missed calls from my mother. I knew something was horribly wrong, because my grandmother had recently fallen ill and was at a nursing home.

I excused myself and called my mother back, fearing the worst.

My grandmother had died an hour ago.

Tearfully, I went back inside and told him I had to go. I hope he didnt think it was an excuse for me being freaked out by the eyedroppers. My grandmother really did pass away.

It may also have been the weirdest date ever for him, given that I had to bag out of it due to a death in my family that occurred during the actual date.

We are now married.

Just kidding. I never saw him again after that night, though he did send me a few texts to cheer me up in the ensuing days. He was a really nice guy.

Lauren Collinson

The guy had been asking me out multiple times at the gym. Instead of being a normal man who would first start a conversation, so we could get to know each other at least a little, he just got straight to the point. No small talk ever. I cant stand pushy people.

He was very persistent and decided I needed to go on a date with him right now, right after my workout. I figured Id give him a chance, even if it was just so he would stop interrupting my workout in the future.

I didnt bring non-workout clothes, nor a towel to shower, but he assured me that wasnt a problem. Im a neat freak so I hate the feeling of being sweaty. (But doesnt everyone?)

When we got to his car, he opened the door for me. I thought maybe he was a gentleman after all, until I noticed he wasnt opening the door for me; he just needed to get all the trash off the seat and floor. His car was incredibly dirty. Again, Im a neat freak. Turn off.

We got where we were going. It was a nice place to have a drink. When the waiter came, I wanted to order a water. Yes, boring choice. I had just worked out, and it was a hot day.

He argued my choice and told me Dont worry. Ill pay. You dont have to get something cheap. I tried to make it clear that it was not about money, but he kept arguing. In the end we settled on getting me a sparkling water. Ugh.

We were about five minutes into the date when he said, I just broke up with my girl. Thats not something you bring up at a first date, but okay. 

I asked him why, and this was his answer: She didnt allow me to mess with other girls, and then when I suggested a threesome, she was against it.

My mind was blown. He said it with a tone of utter obliviousness. Meanwhile I wanted to run.

The worst thing was that my car was still parked at the gym, so he had to drive me back.

Anissa Bellisario

We were set up on a blind date, and I literally could not believe my eyes. She was incredibly beautiful, and very well-dressed. 

We met at a rather nice little bistro patio, right in the heart of the entertainment district in my city. 

We ordered cocktails and appetizers. Our waitress seemed to really love her job, very proactive and friendly. Our appetizers came, and our server put the salad plate on the table. My date's purse was about three inches away. That's when it happened.

My beautiful, charming date immediately devolved into a raging beast. She leapt up, angrily proclaiming that her purse was worth more than the server made in a year. I said to myself, Oh dear, this is not someone I want to spend the night with, let alone the rest of my life with.

I made a single attempt to calm my date down, however, by this point she was already into sentence 109 about how she is superior to the server. 

I spoke up firmly: How dare you speak to service staff in this manner? YOU are PATHETIC, LEAVE! 

The stunned look on her face and her quick retreat allowed me to reclaim my appetite.

Jeff Jahan

I matched with this girl on Tinder, and we hit it off. She liked the same stuff as I did, one of those interests being anime (Japanese animation). 

Upon reaching a point in the conversation where we were deciding on ideas for dates, she promptly suggested I come watch anime at her place. Perfect.

She was in university and was living in student housing. She invited me inside and said that her flatmates were out for the day, so we had the place to ourselves. I was around 95% sure this was my lucky day by this point.

We got to her room. She proceeded to set up her laptop while giving me a naughty smile, and that set my pulse racing! She then took out a DVD case, but I couldnt quite catch the name on the cover. Then she toldme to sit down on her chair. Oooookay.

I remained optimistic, but it got stranger when she took out a notepad and pen. The anime started playing, but oh boy, this was not the anime I had imagined. For those of you who have had the privilege of staying away from the dark side of anime, lucky you. Here I thought I was going to be watching something fun, but instead I was greeted with hardcore anime porn.

She then went on to explain that she would like me to watch 30 minutes of anime porn and then explain how the viewing experience felt. I say No! but she explains the reality of why I was even invited in the first place. 

She wrote reviews of animated porn and used viewer experience as part of her summaries. She said that Tinder was a good place to get (or, from my perspective, BAIT) guys to participate in her review program. I immediately asked where the bathroom was and bolted.

Alen Thomas

After my boyfriend of many years broke up with me very abruptly and in shocking circumstances. I decided to rebound with Marc, who I met through mutual friends at a party.

Marc was cute, in a very classically nerdy way. He was short and blade-thin with glasses and an easy, casual style. He liked the original Star Trek and we shared a lot of the same tastes in music and comedy shows. I accepted an invitation out for coffee, and a home-cooked dinner.

Marc's manners were old-school gentlemanly. He seemed respectful of me wanting to go slowly, because I don't like one-nighters and don't want to jump into the sack with anyone too soon. He saw to my every comfort, made a delicious dinner, and we enjoyed an evening of movies, just the two of us and his dog. I remember not feeling a great physical attraction, but I loved the company.

So you can imagine my surprise when I learned that night that Marc was really Marcia.

Marcia was not transgender. She was a lesbian who preferred to present as male.

I wasn't weirded out by it. I did laugh and say, Well this certainly makes for a very interesting evening! That helped cut the tension. She understood that I did not feel a sexual attraction to women, and it was okay.

It was definitely the weirdest date I ever had. And still one of the best. 

We remained on friendly terms until she relapsed (when I met her, she was a recovering addict) and went back into rehab. After cleaning up, she left the city to escape old influences.

Lisa Stevens

I met a fella. Dark hair, big brown eyes, loved art. We had two very successful dates and I was starting to get that certain spring to my step.

He suggested that the third date take place at his house. He would cook and we could, um, hang around a bit.

My thoughts began to flutter, my lips puckered, my penis did a tap dance. We were going to hook up, and then we'd adopt a bunch of dogs. And do things couples do. Buy dishes. Paint rooms. Rub feet.

I arrived at his door with a tastefully informal bunch of wild flowers and a head full of loosely-arranged romantic fantasies.

Hi Greg welcome! I'd like you to meet my life partner Jason. Jason, this is Greg.

Now call me fussy, but if I'm dating you and youre partnered, I think that you'd better put that information out there, front and center. If this happened today, I'd walk away. But I was twenty. For some reason I felt it was necessary to hide my shock and proceed as if nothing was off.

I chatted. I laughed. I plowed through small alk like a tank rolling through a wartorn town. After a decent amount of time, I blah blahed my way out of there. I made up some excuses: my angel fish needed to be walked, my cactus gets lonely - who knows what I said but I somehow I made it to the door.

On the way home, I picked up a box of brownie mix and a gallon of milk. I didn't even bother to bake it. I just spooned it all down.

Greg Holley

She took offence at my holding a door open for her. She said she didnt need me to open the door for her because women are perfectly capable of opening doors for themselves.

Alright, I said, but in the back of my head I was thinking, Am I supposed to slam the door in your face right after I exit?

I was pretty certain that anyone with manners would have held the door open for anyone after them, regardless of gender.

She also accused me of being sexist when she was crossing the street and I warned her that a car was coming up behind her.

Ive decided that cats are the best companions to have.

Timothy Soh

I was a 19-year-old virgin guy when I started dating this friend of a friend. 

She basically told me that she wasn't going to have sex anymore. I was fine with that, because I wanted to take things slow. She was my first girlfriend, and  also a year or two younger than me.

Then, on one date, I she bought a pregnancy test from the dollar store. I waited by the car. She didn't think I knew what she was doing, but I saw her. In my young mind, I was like… How could I possibly have done this?!

And then it hit me: she was having sex with other guys right up until she met me. Which is fine, but why buy a test when I am literally right there?


Sources: 1, 2

Answers edited for clarity. 

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