Cringe! Team Cosmo's Real Life Dating Disasters

There's no happy ending, but we'll share for the LOLs
Cringe! Team Cosmo's Real Life Dating Disasters

We’ve seen our share of frogs and yeah, some of us found a prince. If you think you’ve had it bad, know you’re not alone! As daunting as first dates can be, they are often memorable... to say the least.

Kavita Srinivasan, Editor In Chief

I was 26 and in the throes of Manhattan’s awful dating scene. Entitled, overconfident and just real pains in the you-know-what, I’d seen enough frogs to write a cynical fairytale of my own. I have a ton of stories but this one just stuck with me for the sheer incredulity of it. A friend set me up on a date with her ‘awesome’ friend. A week of messaging later, we met at this huge bar/restaurant for dinner. It was going pretty well. He was cute, successful and cracked a couple of jokes that actually made me LOL. About 30 minutes in, he excused himself to go to the restroom. After twiddling my thumbs (there was no Instagram or smart phone then) for about 20 minutes or so, I decided to freshen up. A quick swipe of lipstick later, I took the long route back to the table, wanting to keep him waiting. Imagine my complete and utter shock when I saw HIM actually chatting another girl up. Now, that was an absolute first. I ordered myself a drink, walked right up to him, threw it in his face and walked out! And yeah, it felt pretty good.

Jessica Combes, Acting Online Editor

I agreed to go to coffee and a movie with this guy. He thought it would be funny to take me to a coffee shop I said I didn’t like. Then things got a bit awkward when he spilled two drinks on me, so I was drenched and sticky. Then we went to the movie and there was more spillage. There’s only so much soda and popcorn ickiness a girl can take.

Caitlyn Davey, Head Of Content

I was on a date, when the guy somehow thought it was a good idea to enter a burger-eating competition while I was in the bathroom. I came out and he was signing up. And not only did he NOT win the competition, he also didn’t have enough money to pay for his meal and had to be sick afterwards. What.a.dud.

Chloe Bosher, Fashion & Beauty Editor

So when the swipe right came through I thought a public space would be the best option. I saw him before he saw me, and I instantly thought "that is not the same guy as his pictures". So I hid behind a pillar and waited a bit. The thought did run through my head "shall I just leave now, before he sees me?", but then I thought if someone did that to me, karma would defo come back round to hit me. So I got the “I’m here” text message and emerged from behind the pillar. Walked over to meet him, and suggested we just sat on the beach for a bit, I stayed an hour and then made up an excuse that I had to go! (Cringe)


Sanaiya Gabrielle Jhaveri, Junior Writer

I had planned to go out on a date with my crush and my parents knew him. I lied to them and said that I was going to meet ALL of my friends for a movie at the mall (at that time I thought it was cool to keep my stupid date a secret from my mom and dad. But it’s not.) I don’t know whether it was just bad luck or whether my mom and dad knew I was lying but they decided to walk me to the cinema and wait till my ‘friends’ came. I knew the guy was waiting at the cinema already so before we reached, I decided to tell them I was actually going on a date and there was this awkward silence.
They decided to still walk me to the cinema, met him and told us that they’ll wait for us to finish our date and take me home. It was MORTIFYING. My crush and I were so embarrassed that instead of going for a movie we just walked around the mall and ended up bumping into my parents AGAIN which made it so much worse. I still cringe today just thinking about it. I wanted to fall into a black hole and stay there forever. The date was not even worth all the fuss. We didn’t even say much to each other because we were both so awkward. Ugh, I hated it and I’m sure he did too. I had lunch with my parents, I still remember my face being super warm and just unable to make eye contact with them. On the way back home I remember my dad and mom saying “if you told us the truth in the first place, we would have understood.” So, after that day, I always told my parents if I was going on a date or if I was seeing a boy so that I would never end up in an awkward situation again. SO cringe.

Nini Okih, Digital Features Assistant

Said guy and I met at a photoshoot a few months before the “memorable” date. I was the make-up artist and he was there to shoot some content. We didn’t say much to each other but when I was leaving, he finally said “You’re cute” and the feeling was mutual. We decided to meet at a food festival and ended up holding hands because we were having such a good time. He spoke a lot and I listened, then I realised that I had not said anything since he picked me up from the entrance. All I did was hear him talk about his time in France, how he learned to speak French, how he loves to make music, but also wants to be a photographer and a humanitarian and how he isn’t sure of his career path, because he has all these plans. This guy kept going on and on. I couldn’t cut him off, so I just listened. At the end of his date with himself (I was just there to chaperone), he leaned in for a kiss - I was hella confused! Oh and later that night he called me and asked me to help him remember my name.

Jecinta Wangui, Digital Fashion & Beauty Assistant

Imagine sitting across from a cute guy on a date. But, in complete silence. Not by choice though. Rather, it's because you've been solo talking the entire time to a point the embarrassment has just worn you out. I went out with this guy one time and I swear he just looked angry. He didn't say much. Most of the time he only answered questions with either a no or yes. To make it worse, he didn't even ask me anything. I tried to make some jokes and smile occasionally to lighten the mood, but man, he was a tough cookie to crack. He didn’t laugh or smile! At first I thought he was just shy and that's kinda cute. But eventually I just gave up and called it a night. Boy got me wondering why he asked me out if he wasn’t gonna talk?