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Break it up: Here are 5 worst date stories

Worst date stories rank pretty high up in terms of quality fodder for conversation, because who doesn’t love a good chuckle, self-deprecating or otherwise? Valentine’s Day is all about celebrating love, but sometimes, revelling in the antithesis is far more entertaining. Whether you’re attached and want a good cackle at our expense, or are single and need some conviction that dating is just an unnecessary hurdle, we’ve got your back with a compilation of all the worst dates our team has been on.

Baby, you’re no firework

worst date stories
Katy Perry is equally horrified.

I once went out for dinner with a schoolmate who told me he used to frequent the restaurant we were at with his ex-girlfriend. He started ranting about how “psycho” she was, recounting her bulimia and describing in full detail how she would force herself to throw up. (By this point, I was close to doing the same.)

When we were done, he drove me back to my place, and confessed that he liked me. I couldn’t exactly escape because we were in a moving car, so all I could do was listen. I said, especially after that terrible date, that I only regarded him as a friend. He nodded silently, and said he respected my decision. I kept my distance from then on.

A few months later, another mutual friend organised a lunch gathering and we were both invited. I wound up sitting right next to that guy, so we made small talk. I politely asked him what he had been up to lately, and he replied that he had been listening to a lot of music — specifically Katy Perry songs. I adore Katy Perry, so I asked which was his favourite tune. 

He looked me in the eye, and said, “The One That Got Away.” Then he continued eating his food like nothing had happened. Till today, I can never listen to that song without feeling slightly disturbed.

Catfished, coupons, and insurance

worst date stories
Even the best pasta in the world couldn’t salvage my terrible date.

So I was talking to this guy from Tinder every day for about two months. He was pretty impressive, rather good-looking, plays water polo every weekend (aka fit body, right?), an NUS graduate, and sounded like a genuine person. One day we finally decided to meet. I arrived first, and a guy who looked nothing like the person I was supposed to meet approached me. I instantly felt catfished, but wanted to give him a chance. I tried to hide my bewilderment and stayed for the date. I mean, how bad could it be? 

The dude started talking about how he had a dining voucher for a meal from PastaMania, and had been waiting to use it for ages — so he figured our first date would be the perfect time. Let me mention that he is a 29-year-old established man with a solid career. Still very confused (and appalled), I decided, “Uh, okay… maybe he just didn’t want to let that PastaMania meal go to waste.”

When we got our table at the restaurant, the first thing he said was, “Why don’t you buy your meal first; I’ll take care of our bags.” That was when I realised he meant to use the dining coupon for himself, while I got my own meal. After he waited for me to buy my food and (barely) paid for his own meal, we finally got down to talking and getting to know each other — or so I thought. He started talking about insurance. And in that moment, I truly knew I was done. 

Maybe it was bad judgement on my part, but just don’t Tinder, people. You’re probably better off going through an arranged marriage. Your potential partner would at least refrain from using dining coupons on himself on the first date. 

Your love is my drug

worst date stories
Dates and drugs don’t match.

I spent an evening at dinner chatting with this guy who was all about spirituality and the cosmos. I was rather impressed by his ability to talk so deeply about chakras and the inner consciousness, until he revealed he was on two antidepressants daily. Better yet, he topped it off with some cough syrup before meeting me and was still high from it at dinner. Needless to say, I excused myself politely after dinner and made a run for it.

Moth-erf***ing nightmare

worst date stories
Hell probably looks like this.

I’m going to be really honest and say this wasn’t a date as much as a potential one-night stand that I successfully swiped my way. He was an American model (for a high street label, but still, a model’s a model) in town to visit family for a couple of weeks, and had a house to himself, which is all you could really need for an efficient one-night stand. We had a snappy conversation on Tinder, and I got on the bloody expensive cab ride to some estate in the anus of the West.

He told me to wait at a nearby park, because he would walk me to the condo. It took him a good fifteen minutes to arrive. I was ready to up and leave, convinced he was a sh*tty catfish and not worth the trouble, right as this hulking mass of pure man muscle ambled towards me and waved. Jackpot bells abounded.

I tried to create conversation, only to realise that the dude was as dumb as a tool. A tiny bit of a boner-kill, but not a complete deal breaker. Now would be a great time to mention that this fiasco occurred during the heart of the giant moth plague, and his estate was swarming with those satanic buggers. I was too eager to seek shelter in his crib, encouraged by my near-deathly fear of anything with more than four legs.

When his door swung open, I happily rushed in, took my shoes off and saw, to my horror, one of those damn moths just chilling in his hallway. The thing was massive, as wide as my palm, as thick two fingers, and dotted in seven variations of sh*t-coloured brown. Just chilling in my way.

I did the polite thing and asked, “Why the hell do you have a moth in your doorway?”

“Oh, he’s Bob. He’s harmless,” said Mr America.

He then began to explain that “Bob” had been his sole company for the whole stint in the lonely apartment. “He’s been hanging out there for three days.”

I don’t think I’ve ever nope-d the hell out of a potentially great evening that fast before, and no amount of bulging biceps and tight grey sweatpants could salvage the fact that this man had either zero hygiene, or some creepy insect fetish that I refused to be a part of.

Even after the clearly failed night, I got a text two days later. “Leaving the country today. Nice meeting you, and BTW, couldn’t bear to part with Bob”. Good riddance.

Looking for marriage

worst date stories
The first rule of a first date is: You don’t talk about marriage.

He was from another department at work and had been rather persistent at going out for a drink. One day, I relented. So we met at one of my favourite bars, where he proceeded to quiz me about marriage, children, my views on education, and pretty much everything else you shouldn’t talk about on a first date. If that wasn’t bad enough, he proceeded to explain how he would treat his wife like a daughter, and that was the one right way to approach true love. 

I left after one drink. 

Beatrice Bowers
Features Editor
Beatrice Bowers writes about beauty, drinks, and other nice things. When not bound to her keyboard, she moonlights as a Niffler for novels and can be found en route to bankruptcy at your nearest bookstore. Don't tell her boss.