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10 Worst Date Stories In Singapore That Will Make You Feel Better About Your Love Life

Getting stood up by your date can be a terrible feeling, but I realised sharing such sad moments with friends can turn the awkward and tragic moments in life into quite hilarious banter.

Trust me, these 10 worst date stories in Singapore were told with humour and theatrics, and got the entire office laughing!

1. Ending The Date With Finesse

“So basically, I went out with this guy, and we were just getting to know each other. We weren’t dating yet. We both grabbed dinner somewhere that wasn’t too fancy. It was pretty chill and all, with casual chit-chat here and there.

Usually, he’ll send me home, so that day it wasn’t anything out of the norm. He sent me to my doorstep at my condo. But this time, he pulled me to a staircase just as we reached.

And BAM! He flopped out his dick. I screamed and ran into my house after that.”

2. When A Joke Becomes Overdone

“We had mutual friends and DM-ing was a thing back then. And she asked if I wanted to go to the airport to take a look at the Spongebob exhibition.

While walking side by side, she started bumping against my hip with her ass. The first few times it was funny, but holy f*ck, it became so irritating afterwards. She continuously did it, so whenever she tried bumping me, I walked a little faster.

And after the first few times she missed, she started to poke my ass with her finger and she said this was what girls in girls’ schools did. I just tried to smile and not show that I was creeped out.

I came up with an excuse, saying I had dinner with my family and left afterwards.”

3. Birds Of A Feather Flock Together

“The date went well, from dinner to just chilling by the sea at East Coast Park. We continued by driving to a secluded carpark along ECP and parked at the corner. Things got really steamy at the back of the car. But wait, you have to know what position I was in; I was behind her facing the passenger seat window.

While things were rockin’ on, a taxi drove in and parked beside us. The best thing was that the taxi driver had a lady seated shotgun, who put both her legs up to his shoulders.

And the next thing I knew, both the lady and the taxi driver looked through their windows and made eye contact with me, while I was doing it. They then sped off right away.”

4. When It Could Not Get Any Worse

This dude DM-ed me through Facebook and it escalated to him asking me out for dinner.

I had him pick me up at my place. On the way to the restaurant, he told me he’s deaf and he explained, “I can’t really hear that well so if I raise my voice, that’s the reason why.” Taken aback, I tried to be as understanding as I could.

Upon reaching the place, the waitress approached us and he shouted, “TABLE FOR TWO”. I was so embarrassed because the staff and everyone inside started staring. They even sat us down at a really secluded table, isolated from all the other customers.

During dinner, an old couple walked past our table to pay the bill, and he mentioned that the old man was staring at him.

I tried calming him down, but he rebutted saying his martial arts coach taught him that he cannot have anyone looking at him before he looks at them. He went on for the rest of dinner looking at literally everyone that walked past us, to make sure they weren’t looking at him.

With so many clear red flags, I was very eager to leave after dinner. Thank God I managed to ‘ghost’ him.”

5. The All-In-One Asshole

“He was a Tinder date and we had been texting for a week before we decided to go to a movie. We were supposed to meet at 7.30pm, but he got “caught up in traffic”. He kept me waiting for two hours, for f*ck’s sake.

When he arrived, we were five minutes away from the start of the movie, and yet he made us go to McDonald’s to grab food because he was hungry. What’s more, he didn’t have enough cash on him, so I had to pay for him.

During the movie, he kept sniffing my hair, despite me trying to sit at the far end of the seat away from him. That made me really uncomfortable. After the tormenting experience in the theatre, I wanted to head back because it was late.

He offered to send me back, so I thought at least he had a certain level of courtesy, even though he put me through all that shit. Upon reaching my place, he pulled me in and stuck his tongue down my throat out of the blue. I pulled away, wiped my mouth and ran back home.”

6. The Catfish

“I was heading to the club, and I thought it might be a good opportunity to invite this Tinder girl along and meet her for the first time.

When I picked her up at her place, the person I saw coming towards me was definitely the girl I was talking to, but only uglier. She had a gremlin-like frame and slightly hunched back, coupled together with a face only a mother could love. It took me a good minute to realise that everything I’d seen online was photoshopped.

At that point in time, the only thought that went through my mind was to run and get out of there. I tried holding some small talk while carefully devising an escape plan in my head. Time was running out, as she pulled out her phone to book an Uber to the club. I knew that I had to do something or I would end up in the club with her.

“I’m not really feeling that great, and maybe clubbing tonight might not be the best idea.” That was the best excuse I could think of. After I said it, she gave the saddest look I’ve ever seen. Till today, the next line I said turned me from being a dick to the worst guy ever.

“How about we go grab some supper instead, you can go change into something more comfortable and I’ll wait for you.” This was the last thing I ever said to her because after she went to change, I ran off and flagged down a cab to escape.

I blocked her on every social media platform and have never looked back since.”

7. When The Ghost Of His Ex-Girlfriend Still Haunts You

“There was this guy that I met through a meeting for some school project. I’m not sure if it was his nerves, but he started to say stuff like, “oh your name is really nice”.  Then he started to tell me how his ex-girlfriend has the same name as me.

This was cool with me, but things escalated when he started telling me about how his ex-girlfriend turned lesbian, and left him. He became really aggressive, asking me if I’ll become lesbian too. After he grabbed my hand, I pulled away and told him off.”

8. TFW Your Best Friend Becomes A Cockblock

“I went on this Tinder date, and he was pretty cute. Everything was going well. We started drinking, and I thought everything was good, so we went bar hopping.

We found ourselves in a bar with a dance floor. And while we were talking at a table, my friend who happened to be nearby came over to join us. I thought she was just being friendly, because she even bought drinks for us.

She got really high, and the next thing I knew, she spilt her drink all over my date. Subsequently, she pulled him onto the dance floor and started dancing with him. She had her hands all over him, and even started grinding!

Thank God, he wasn’t really interested in her and managed to talk my friend into getting in a cab back home.”

9. From Classy To Savage

“I met this guy online and he was pretty cute. He offered to pick me up and drive on our first date, which was sweet of him. I was wearing a sheer top that day, and halfway through dinner, he just looked at me and asked if I was wearing a black bra. (Yes, I was.)

He didn’t ask anything after that, and the night went on as per normal.

Then when we were in the parking lot, he started playing some jazz music. While we were talking, he just looked at me with the “I’m about to kiss you” look. He suddenly leaned over, pushed my chair back and commanded me with the deepest voice ever:”I want to unlace your bra now.”

I’ve never screamed so hard in my life. I kicked him and ran away in the open carpark.”

10. The Nosey Parker

It wouldn’t be fair if I listed out everyone’s worst date and missed out on mine right? So yes, I have my own personal tale to share.

She was someone whom I met online, and her profile just lacked close-up photos. So it was tough to make out the details of her face. I decided I had to meet her IRL to get a better gauge.

OMG, her nose was so huge it felt like it was intruding my personal space! I took on my friendliest persona and tried my very best to not show any signs of distaste.

During dinner, I spent a long time holding the menu up while making plans on my phone to leave. I wasn’t too sure if she noticed, but when the ramen arrived, I angled my sitting position so that the seaweed in the bowl would cover a fraction of her face.

It really aided my appetite.

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If you think you’ve had any dates that can compete with this list, do share with us in the comments below!

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