Singaporean women share their worst first dates – Part 2

Dating in Singapore can be a rollercoaster of emotions, from the exhilarating highs of a perfect match to the cringe-worthy lows of a terrible date. Here, we’ve gathered stories from women who’ve braved the Singaporean dating scene and lived to tell the tale. 

Be warned — these dating disasters will have you shaking your head in disbelief and thanking your lucky stars for your own, perhaps, relatively normal dating experiences.

Who does that?

“First date and I was already the star of the show — literally. My date had set my selfie as both his lock screen and home screen. 

Needless to say, it didn’t work out.”

Lied about his age, borrowed money from me

“I met this guy on Tinder who claimed to be two years older. Turns out, he was five years younger. Yikes. 

Our first date was a comedy of errors — he was so quiet and awkward, I thought I was dining with a mime. When it came time to pay, he insisted on footing the bill, despite suggesting the expensive sushi place. Then, the kicker: he asked me to spot him $20 because he only brought $50.

Later, he texted me, “I wanted to show you my shy side first and didn’t want to unleash my wild side. Ready for the next date?”

Nope, thank you very much.”

He tried to convert me to his religion

“It started as a promising connection, but things quickly took a turn. My date, who was of a different faith, initially seemed open-minded. He assured me that he wouldn’t pressure me to convert. 

However, as we went on more dates, his true intentions became clear. He implied that by the time we were ready for marriage, he would’ve already somehow “convinced” me to change my beliefs.

It was a red flag that couldn’t be ignored. I ended things immediately, realising that a relationship built on manipulation and coercion was not one I wanted to be a part of.”

Asked for sex after a silent drinking session 

“My first date with this guy was a bit of a disaster. I arrived slightly buzzed from a previous drinking session with my friends, so I was in a pretty good mood. We ordered a pitcher of beer, and I tried to make conversation, but he just stared at me. After a long, awkward silence, he suddenly blurted out, “We don’t have to talk, you know.”

I was taken aback. We finished our drinks in uncomfortable silence, and after getting the bill (which I paid for BTW), he casually asked, “So, my place?” 

Yeah no.”

Technically, it wasn’t a date 

I matched with this guy on Bumble, and he seemed like a decent enough chat. We were texting back and forth when all of a sudden, he suggested meeting up at a park in Pasir Ris that very day. 

I live on the opposite side of the island, but, ever the optimist, I agreed.

After a long and tiring journey, I arrived at the park, only to find that he had ghosted me. He deleted his Bumble profile and wasn’t responding to my calls or texts. Talk about a major bummer.

But hey, at least I got a good meal by myself at a steak restaurant, so thanks, I guess?”

Horny NS boy 

“I matched with this guy on OkCupid who seemed like a normal, fun person. He was cheerful, easygoing, and had a great sense of humour. Or so I thought.

Then, he started veering into strange territory. Every conversation, no matter how innocent, would somehow turn sexual. If I mentioned I’d just eaten, he’d reply with something like, “I’d rather eat you”. Or if I told him I got caught in the rain, he’d say, “I like it when you’re wet too”. 

It got even weirder. He’d regale me with tales of his sexual exploits, including public sex in handicapped toilets and cinemas. He’d brag about his fingering skills, claiming to have brought multiple orgasms to his ex-girlfriend. I’m pretty sure she was just faking it to make him stop.

Needless to say, I stopped contacting him soon after.”

Talked about having kids one hour into the first date

“I had matched with this guy on Tinder, and we had agreed to go watch a movie.

Things were going okay until about an hour into the film, when he suddenly blurted out, “If this all works out, our kids will be mixed.” I was so taken aback that I just laughed nervously. And no, he wasn’t joking.

He then proceeded to tell me a long, dramatic story about his ex-girlfriend, a single mother who had gone back to her ex. I don’t know why he thought that was the appropriate conversation topic for a first date.

To top it all off, he posted a selfie on Instagram, wearing my glasses and captioning it with a heart emoji. Right in front of me!

After that one date, he just wouldn’t take the hint that I wasn’t interested. He sent me long, emotional texts, acting like we’d broken up. It was the most bizarre and cringe-worthy experience. He was 27.”