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What's the Most Embarrassing Date You've Ever Been On?

What's the Most Embarrassing Date You've Ever Been On? main image

Depending on your perspective (i.e. whether you're single or in a relationship), Valentine's Day is either a nice opportunity for a romantic date or a day for miserly grumbling about how you're going to die alone.

Of course, if it's the latter, one way to fix this is to try and arrange a Valentine's date by furiously swiping right on Tinder in every spare moment between now and Wednesday. Be careful what you wish for though, as the course of true love never does run smooth and your Valentine's "dinner and a movie" could quickly turn into a nightmare date which will haunt you for the rest of your life.

Sound like we're laying it on a bit thick? Here are some of the worst and most embarrassing dating stories from the TopUniversities team.

Embarrassed Emily

During my first year of uni, right before the start of the second semester, I went on a night out with a group of friends.

There was a cute older-ish guy at the bar who I started chatting to, one thing led to another, and we went back to his.

His flat was amazing, on top floor in the centre of the city, overlooking the river - and he paid for everything all night. I couldn't stop bragging about it afterwards.

The next week, our electives started and I walked into the first tutorial and stopped dead in my tracks. I'd shagged the professor.

Leftist Lisa

I once went on a date with a UKIP voter. I met him on a dating app - he was a cameraman for Masterchef, had good hair, was 23 - nothing that would signal sinister beliefs at first glance. The date was just before the general election in 2015, when UKIP still had some prospects of winning seats, and I mentioned on our second date that I found the “normalisation of UKIP” with younger voters really frightening.

In response, he blurted out that thousands of immigrants were allowed into the UK unchecked, and that some had histories of sex abuse like "raping children" and the UK government should make sure to "filter out the sex offenders".

So yeah, he was a UKIP voter and a racist. One lesson learnt from that, have a more rigorous pre-date vetting system in place.

Forgetful Francesca

One night at the pub, I was chatting to this cute guy, who was doing his PhD in the ancient history of Birmingham and I drunkenly gave him my number. A few days passed and he texted me, asking to go out on a date.

We decided to meet at the Royal Festival Hall in London. I thought he’d stood me up as I was walking around for ages, trying to spot him in the crowd by the entrance. Eventually, I got a phone call from him, but still couldn’t see him.

It turns out, I gave my number to another guy that night as well. I didn’t recognise him. At all. We went on a date that lasted 30 minutes until I had to pretend my flat had a leak to get out of it.

Over-thinking Oliver

Maybe don't start a relationship by drunkenly promising a grand romantic gesture. That comment, admittedly made in jest, left me panicking in the days in the run-up to what was my first date at university. To make matters worse, I was in a new city, with no clue what there actually was to do on a date.

Asking my housemate what he does when his girlfriend comes to visit wasn't any good (turns out the answer was they didn't really leave his bedroom), so I was left to walk the streets hoping to come across something fun/romantic/quirky/interesting (please find me interesting) to do.

In the end, I admitted defeat. We went to Cafe Rouge and she proceeded to tell me repeatedly how weird it was to go to Cafe Rouge and why couldn't we have just gone to the pub. Turns out she'd completely forgotten my alcohol-fuelled promises from when I asked her out.

Slovenly Sarah

At school we had a very strict uniform policy, and if we weren't "dressed correctly" the teachers would pull us to one side and make us tidy ourselves up.

On one occasion, I was standing outside a classroom when two arms grabbed me around the shoulders. I saw from the arms that it was a guy wearing a white shirt and naturally assumed it was my boyfriend.

I turned round and went to kiss him, only to discover it was the headmaster trying to tell me to do up my tie.

Clumsy Colin

We'd gone out for a iced coffee on a hot summer's day and was watching my country play in Euro 2016. I was really into the game, but when I jumped to celebrate a goal (something good normally, right?), I managed to overturn the table, covering the girl I was with in iced coffee and ice cream.

Mixed-up Mary

One Friday evening last summer, I went to the bus stop a bit tipsy after some drinks at the pub. There was a dog at the stop who seemed very happy to see me and I love dogs so I made friends with her. Suddenly, I noticed her human who was even cuter than the dog. We chatted while we waited for the bus, and then continued to do so all the way home. I got off the bus without exchanging numbers so I tried to find him on a dating app by using my location. Eventually, I thought I'd found him and we planned a date. Unfortunately, when we finally met I realized it was the wrong guy. We had nothing to say to each other, so I had a very awkward drink at the pub and then left.

Terrified Terry

One of my first proper dates was with a guy in my hometown. We went to one of those “horror attractions” where you walk through a haunted house and scary things jump out at you.

Unbeknownst to me, I was with a total wuss. We came to a section with very fake corpses hanging from the ceiling, and a maniac chasing us with a plastic chainsaw. The guy I was with panicked, freaked out and pushed me headfirst into the chainsaw man. I had to grab one of the fake corpses to stop myself falling and we all landed in a pile on the floor.

Kissing Kate

When I was 18, I was dating a guy who was about 25 and had a really nice, expensive looking car. On one night out, we were all pretty drunk and a car pulled up at the end of the road and honked. I went over to talk to the driver, which everyone assumed was my boyfriend.

Unfortunately, a friend who was enjoying the night on a different level to the rest of us, decided to run over, lean into the car and full on snog the guy inside. As it turned out, it was my dad.

Got a bad date story of your own? Let's hear about it in the comments below.

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1 Comment

I can share with you my most embarrasing date: I started to date one beautiful girl without any crazy ideas in her mind ( I was so mistaken). So we had decided to stay at her apartment for the Friday night and I was, you know, pretty excited. After few glasses of wine she has come to me very closely and whispered: "Do my homework for me" if you wanna see something interesting. I was shocked and speechless. She was insisting on that! I got a dilemma: to say goodbye and forget about it or to do her homework to get a real date with crazy woman. I was really confused and I decided just to take my clothes on and never see her again.