Being single in Singapore can be brutal. For prime examples, just look at these dating horror stories that Singaporeans – both male and female – have shared. Someone posed the question on Reddit under r/Singapore, and boy, did Singaporean Redditors deliver. Here are some of the most cringey ones.

*Some accounts have been edited for length and brevity

The one with the criminal record

“Back when I started working, I befriended this girl. We were both single and would hang out and talk about our dating adventures. She offered to set me up with a male friend of hers. She showed me his Facebook profile and I Googled his full name. Turns out, he’s a convicted molester. I came up with an excuse to turn down the blind date and eventually the friendship with her died too.” – Morning-gloria

Wait, what?

“First date. Guy had my selfie as his lock and home screen. Safe to say it never worked out.” – littlesuperherogirl

Race to the finish

“Car sex commenced but when I was asking her where she’d like me to finish, she told me to cum in her. I asked if she was on the pill and she told me no, don’t worry, she knows her body, she won’t get pregnant. I just ignored her claims and thought I’d just cum outside later on.

When I was about to finish and she saw me visibly pulling out, she actually wrapped her legs around me to prevent me from doing that.

Imagine the odd sensation of horror and orgasm occurring at the same time. I shoved her and managed to cum outside and I could only hear her go ‘nooo’. Safe to say that was the last date with her.” – funontheinternet123

This beer boo-boo

“Went out with a girl, didn’t really hit things off with her, chemistry was off. After dinner I decided to go back… but she wanted to hang out. So I thought, let’s go to a bar. I mean, it’s a nice place to try and salvage the date, plus maybe alcohol would loosen things up?

Upon reaching, I left my card on tab, and went to the toilet. I told her to order something for me.

Came back to two towers on the table.

She goes, oh by the way, I don’t drink ah. But got promotion now, so get two and the second tower is 50% off. I got so drunk, I puked in the lift.” – Intentionallyabadger

Fork this, I’m out

“I once went out with a guy from Tinder. He held his fork like a two-year-old who had just learnt to use it and shoveled food. I kept telling myself not to be shallow but my eye was starting to twitch. Then he said his mum was trying to get him to marry his cousin. [First] cousin…” – droseng

A ride on the wild side

“Met a guy on Tinder who said he’s two years older than me. Turns out he’s five years younger. OK, no big deal. Was super quiet and awkward throughout the meal. I offered to split the bill but he said that was rude since he’s the man and he should pay. OK, fine, sure, let him have his ego. Then he went to the cashier, came back and asked me for $20 because he’d only brought $50. It was his idea to go to the expensive sushi restaurant by the way.

Went home and he texted: ‘Wanted to show you my shy side first. Didn’t want to unleash my wild side. Ready for the next date?’ Nope.” – eilletane

Got cash?

“She wanted me to fetch her from her workplace even though we were just going to hang near where we lived at (we live kinda close).

She suggested we go karaoke, but then she didn’t want to sing. Spent most of the time talking about her ex she just broke up with, and didn’t offer to pay for her share of karaoke or dinner. I figured I just wouldn’t go out with her a second time. A few weeks later she texts and asks if she could borrow money. Never blocked anyone so fast.” – j_fat_snorlax


“Met this guy for the first time at a bar and I had been drinking prior, so I was already pretty buzzed. After we ordered a jug each, in my happy-drunk state I began to ask him how his day was. He stared me down for a good half-minute, and just said, ‘We don’t have to talk, you know.’ O-kaaay. We drank our beers in absolute silence. After I asked for the bill (which he didn’t even offer to split so I ended up paying for), he said, ‘So my place?’ Um.” – existentialost

BTO ai mai?

Not my experience but my friend’s. It’s the second date and she was like, ‘Come, let’s go to HDB.’ He nearly choked on his drink and let out a flabbergasted ‘What for???’ She replied with, ‘To see flat lah!!!’ That was the last time he went out with her.” – microtek789