Singaporean women share their worst first dates – Part 1

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.

From online legend to real-life flop

“I’d heard whispers about him online, about a “white knight of pleasure”. He was supposed to be this legendary fingerer, a real wizard with his digits. When he slid into my Instagram DMs after following me, I was intrigued.

We rendezvoused at a dimly lit café in Holland Village, where we had coffee and some hushed conversations. After that, we headed to his hotel room. Things were heating up, and I was ready for the main event.

But then... poof. The magic disappeared. Turns out, he was more of a magician’s failed intern than a magician himself.

He ripped off his jeans, revealing a limp, flaccid disappointment. To make things worse, he wasn’t even wearing any underwear under his jeans! Despite making out for quite some time, his, erm, wand just wouldn’t cooperate. 

He was huffing and puffing, growling like a frustrated puppy, while I just sat there, dumbfounded and a little grossed out.

I mean, I’d heard of stage fright, but this was ridiculous. It was like watching a comedy sketch.

Eventually, I told him to stop. I got dressed and left, fingerless and bewildered. I guess some legends just can’t live up to the hype.”

He didn’t know where Dakota was 

“I was on a date with this guy who was, let’s just say, a little sheltered. Despite being in his late twenties, he has never been to Universal Studios or had a girlfriend.

After our third date, I mentioned I was heading to Dakota to meet a friend. His response? A blank stare and the question, “Where’s Dakota?”

“Bro, don’t you take the MRT?” I lashed out. That was the final straw. I realised I couldn’t be with someone, a Singaporean nonetheless, who was so clueless about his own country.” 

From suits to sadomasochism

“I went on a date with this finance bro who looked perfectly normal, even a bit too normal. After dinner, he suggested we head to a place he rented in the CBD. Intrigued, I agreed.

When we arrived, I was greeted by a sight that could only be described as a BDSM enthusiast’s wet dream. The walls were adorned with an impressive collection of butt plugs, neatly arranged like trophies. There were whips, chains, and even a sex chair. It was like walking into a real-life dungeon, and not the mediaeval kind.

He tried to assure me that it was all for “decoration”, but I couldn’t shake the feeling that I’d stumbled into a horror movie. The soundproof room, the drinks he offered... it all felt a bit too much and suspicious. 

Looking back, I realise how dangerous the situation could have been. He could have locked me up in that soundproof dungeon and who knows what horrors could have unfolded. I’m just glad I managed to escape unscathed.”

He took my virginity and confessed that he was gay…

“My first serious relationship in university took a surprising turn. After becoming intimate, my boyfriend confessed that he believed he was gay and had only pursued a relationship with me out of curiosity. It was a shock, to say the least. The experience was deeply upsetting and it took a long time to process.

After our breakup, I learned that he had quickly moved on to a relationship with another man. Up until this day, they have been together for more than five years. It was really traumatising, to say the least.” 

Mummy’s boy 

“My relationship of six (!!) years faced an unexpected obstacle when his religious, conservative mother began to exert her influence. 

Despite her initial neutrality, her disapproval grew stronger over time. She deemed me “not traditional enough”, and urged my ex to break up with me. Being a mummy’s boy, of course, he listened. We were in our mid-twenties.” 

The fork-fumbling cousin-lover

“I once matched with a guy on Tinder who seemed decent enough. We met up at a café in town, and things were going smoothly until I noticed something... peculiar. He was eating like a child, shovelling food into his mouth with a fork. At first, I tried to ignore it, but it was becoming increasingly difficult.

The conversation was equally bizarre. He casually mentioned that his mother was trying to set him up with his cousin. A direct cousin. I couldn’t believe what I was hearing. It was like a scene out of a strange, dysfunctional family sitcom.

I politely excused myself, thanking him for the coffee. As I walked away, I couldn’t help but feel a mix of amusement and pity. I’d dodged a bullet, that much was certain.”