Reddit users in Singapore have been sharing their worst dating experiences, revealing a collection of bizarre, cringe-worthy, and downright unsettling encounters. From insurance pitches during dinner dates to overly protective friends and demands for payment, the stories paint a humorous yet cautionary picture of the Singaporean dating scene.
Singapore ans have taken to Reddit to share their worst dating experiences, and the responses did not disappoint. One woman thought she was going on a regular date, but things took a bizarre turn. Before meeting up, the guy posted a picture of his shoes on IG with the caption, “Going on a date today, wish me luck,” which she found cute. He took her to a cozy restaurant near Haji Lane, offered to pay, and ordered a few dishes and cocktails.
Then, out of nowhere, he whipped out his iPad and started pitching her an insurance policy. She sat there, absolutely stunned, while he tried to close a deal over dinner. “After 1 hour.. he realized I am not going to sign anything and he just left. Like he just packed his stuff machiam like finish exams already. Didn’t even say bye,” she wrote. The woman ended up paying for the dinner, which cost around $90. To add insult to injury, the guy later posted an IG story calling her “high maintenance”. This man thought he was in for a great date after a customer asked for his number and happily agreed to go out with him. But when the day arrived, she brought an unexpected guest — her overly protective friend, who made it clear she was there for “safety reasons”. This friend dominated the entire conversation and she also kept flashing a penknife, making the whole thing feel less like a date and more like a hostage situation. To top it off, she expected him to foot the bill. “I did no such thing and she started talking down to me again. It had gotten so nasty, I told them I needed to leave to attend a sudden issue. I simply left. We never contacted each other again and that was that,” he said. A woman shared that her date seemed normal at first, so she allowed him to walk her home. But the moment they reached her door, he insisted that she must be living alone and demanded to be let in. When she refused and shut the door, he began ringing the doorbell and knocking non-stop, repeatedly asking her to let him in. “Of course I didn’t, and he texted me 30 mins later that he’s finally leaving….So ya, I never let anyone walk me home anymore. I block him from tele and dating apps and he still found me and kept matching me months after. Legit crazy,” she wrote. One man shared a story about a time when his date bluntly told him that he was “shorter than she expected”. “It hit my insecurities really hard, but I pretended to be okay and said, ‘Haha, isit!’ and dismissed it,” he said. Throughout their time together, this woman only talked about herself, bragging about her academic achievements, how she worked hard for a scholarship, and how she led her band to win an award. She showed no interest in him. “She was the most entitled, narcissistic person ever, which, up until today, is the single worst date I’ve ever been on in my life. I blocked her immediately,” he said. The woman who started the thread also shared her own disastrous experience. She explained that she had told her date she would be arriving a bit late, so she asked him to order first. “When I arrived I apologized for being late, he didn’t react. I asked him why he didn’t order anything (the restaurant had a QR code ordering system ) and he said because he does not have a credit card or any bank card,” she wrote. “His wallet was on the table together with his phone and I could see that he had a few cards peek out— one actually looked like the DBS bank card,” she said. She let this pass, however, and went ahead to ask what he wanted to eat (she was okay to pay for it). He just stared at her blankly and said “he didn’t know”. After a long pause, she suggested they get fries to share, but once again, he didn’t respond or react. She even asked if he wanted drinks, only to be met with more silence. After not having eaten all day, she started losing patience and asked why he was so quiet when he had been normal on the app. His rude response was, “You will pay, right? Because I don’t have a card. Why don’t you pay, and I’ll figure out a way to pay you.” At that point, she cancelled the order, got up, and left without saying a word. She blocked him while walking and decided to do some window shopping before heading home. One woman who works in the tech industry shared how her date spent most of the time complaining. He started by talking about his ex and how she lost money from their joint investment. Then, he shifted the conversation to his autoimmune disease, turning it into a pity party. “Then he suddenly started interrogating me and asking if I had ‘any medical issues he should know about.’ At this point, I felt like a piece of livestock in a slaughter house,” she said. As if that wasn’t enough, he complained about his job, expressing frustration over his low salary despite his master’s degree in maths. He even asked for career advice on how to transition into tech. She never contacted him after that
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