We Asked Singaporean Men to Share Their Worst Dating Horror Stories — Buckle Up

Perhaps in an alternate universe, telepathic technology will be a commonality, and we would be able to skip first dates altogether. But alas, that is not the case in our current reality. First dates are often significant—they set the impression and are the deciding factor for future dates. As much as small talk can be tiring, we must acknowledge that small talk is the gateway to having more profound and more meaningful conversations. Getting to know someone from scratch is hard enough, but imagine having a horrific time during the date, now that’s the icing on the cake.

We’ve heard countless stories from women on horrible first dates; personally, I could write a whole book about them. But seldom from the male perspective. So, I pulled aside two of my close guy friends, and, dangling the prospect of bubble tea and cakes, asked that they relate their worst dating experiences to me.

Sean, 23, Food Writer

The One With Hidden Intentions

“I thought she was pretty and decided to swipe right on her. I was quite surprised that we matched. I reached out to her first, and she replied within a few hours. We started with small talk—how are you? What are you doing? The usual getting-to-know-someone type of conversation.

Somehow the conversation reached the topic of my photography. I shared with her my Instagram photography account, and she seemed very interested in my work. She started asking me about the ins and outs of my photography—what kit I use, who I shot with before, how often I shoot.

At this point, I genuinely thought she was merely supportive and curious about my work, which made her even more attractive. We quickly exchanged numbers and began texting. After about three weeks of texting, I asked her out, and she promptly agreed. 

We met at Mos Burger, and as a surprise, I brought my camera along as well. After our pleasantries, we grabbed a nice meal and bonded over dinner. Throughout dinner, I felt like we were connecting, and I genuinely enjoyed spending time with her.

Out of nowhere, she pushed the subject of our conversation towards my photography which I found weird. I obligingly answered each one of her questions, slowly growing more doubtful of her intentions.

After what seemed like forever, I couldn’t help myself any longer, and I finally asked her why the intense curiosity with my photography. She sheepishly revealed that she only went out with me so that she could have her photos professionally taken.

At a loss for words, I laughed it off and tried to make light of the situation. The date quickly turned sour after her admission, and we parted ways. At least she had the decency never to contact me ever again.”

Tony, 23, Video Extraordinaire

Tony shares four horror stories that might have put him off dates—forever.

Better Be Safe Than Sorry

“We met during a part-time job while I was in Polytechnic. It was an events job, and I was operating a booth at a carnival with another fellow part-timer that I met there. Throughout the gig, we started talking and got to know each other—I felt that we hit it off well. We exchanged numbers and started texting for a bit before she asked me out.

I thought about it and realised that I had nothing to lose and agreed to the date. To be frank, I didn’t know what to expect out of it. We set a date, met at Bugis MRT and headed to a cafe. At the end of the date, she conveniently pulled out the classic blue insurance folder.

I’m pretty sure by now you can guess how it ended. She said, “Can I have a moment of your time?” And at that moment, I thought to myself ‘ah crap, here we go again.’ I went on a date with a girl who just wanted to sell me insurance.”

She Only Wanted Me for My Money

“We were CCA mates for some time and had not spoken much until we were assigned to collaborate on a project. Through this project, we spent a lot of time together and naturally with all that time spent I got to know her better. After which, I asked her out after an event that we both participated.

I have a thing for cafes—so we headed to one for our date. We had a good meal and mostly spoke about our CCA and life in general. Initially, we agreed to share the cost, but she said that she had no cash and asked if I could cover for her first. Of course, I agreed, it was just a meal for me.

When we were at the cashier, right before I was about to pay for our meal, suddenly, instead of asking for the bill, she started to order even more food, which left me confused and bewildered. I confronted her and asked her what she was up to. She said, “Oh, I’m just buying food for my family.” I thought to myself, ‘Maybe her family does require food’.

She told me that she’d return me what she owed me another time and I hesitantly agreed. We never went on another date, but thankfully she did return what was owed.”

The One With the Decoy

“She slid into my DMs and immediately asked me out which was puzzling. I opened the message with suspicion and proceeded to talk to her with caution. I was trying to suss out her intentions, and after a week of texting back and forth, I consulted my friends on what to do, and they told me ‘what’s the worst that can happen’. And so I went on a date with this mysterious girl.

To my surprise, she looked better in real life than in her photos. We met at Tiong Bahru—the land of hipster cafes. As we walked to the cafe, I interrogated her on how she randomly found my profile on Instagram. She brushed it off and said that she saw me at a volunteering event. Taking her for her word, I didn’t question her further.

We reached the cafe, and after ordering the food, she revealed to me that she was actually a decoy for her friend, B—B was the one who was interested in me. To say I was confused was an understatement. Soon after, B came and joined us at the cafe.

I felt cheated but decided to give B a chance and let her explain herself. She apologised and said that due to her lack of confidence, she was scared to approach me and get to know me from the get-go. And she understood if I wanted to leave.

In the end, out of politeness, I tolerated the awkwardness of the whole situation and conversed with the two friends until we finished our food. We parted ways, and after a few days, B messaged me and asked me out on a proper date this time, but I rejected her because we lacked a connection.”

Marriage Proposal on the First Date

“It was an event in which we brought kids out to the museum—I was the in-charge; she was the volunteer from my team. After the trip to the museum, she invited me out for a cup of coffee. And riding on the high of the successful event, I readily agreed to her proposition.

We travelled from the museum to Dalkomm Cafe and got to know each other at the cafe located at Centrepoint. We ordered our coffees and took a seat. About half an hour into the date, out of nowhere, she received a call—it was her mother. During the phone call, she asked her mother to join us, and before I could object, her mother seemingly appeared out of thin air.

I immediately felt uncomfortable upon her mother’s arrival, and I quickly tried to find an excuse to leave. But before I could, her mother started to bombard me with questions. I felt like I was transported back to Chinese New Year—where relatives would ask all sorts of questions under the guise of showing concern.

At some point, she even tried to convince me how good her daughter was and asked me to consider marriage. What triggered me to want to leave immediately was when her mother wanted to invite me back to their place for tea. That was when I faked a phone call and ran away.”

It seems that our friend Tony has had nothing but a string of horrific first dates. Fellow men out there, if you’ve faced something similar, don’t be discouraged. There’s someone out there for all of you. Here’s to better first dates for all of us!