7 S'porean stories of terrible dates & relationships to spoil the V-Day feels

No way we could have made these up.

Mandy How| February 12, 06:33 PM

It's coming and there's no running (hiding at home is an option, though).

Depending on how susceptible you are to social norms, Valentine's Day is either a day of many emotions or just another Thursday.

Either way, here are seven stories of terrible romantic experiences that have actually happened to us. But they're all the better to lap up if you are single and bitter.

1) Dumped by his mother

- A random female Mothership staff 

I once dated this guy for three years, from his JC to army days (I was a year younger than him).

Then he dumped me after he ORD-ed. To be more specific, his mother dumped me.

The whole thing started on New Year's Eve 2009.

We were halfway through the celebrations and watching the fireworks when he told me he had to go -- his mother had arrived to pick him up.

Okayyyyyy, I thought.

The next day, he called and told me that things weren't working out.

Then he passed the phone to his mother, who officially ended the relationship.

Apparently her son had gotten into SMU, and she didn't want me around to distract him, especially when I had less-than-stellar grades (I flunked my A-level exams and had to retake it).

My company was fine during his army days, though ?

Subsequently, I asked to meet for one last time (for closure) on the day of his 21st birthday (so that he'll remember it forever, ha).

Unbeknownst to him, I had brought my parents along.

When we eventually met at the basement of his apartment building, a fight broke out between his mum and my mum.

It was nothing physical, just plenty of yelling.

The break up was shit when it happened, but funny in hindsight.

2) Plenty of prospects

- Sulaiman (male)

I matched with someone on Tinder and went out for dinner and a movie. Simple and classic.

We seemed to click and I thought things went well, but she didn't reply as enthusiastically after our first meet-up.

I thought it was best not to push things, so I stopped talking to her.

After about a month, the same girl sends me a message, asking to meet up. I thought things were looking up! So I agreed to another dinner date.

It was as if we had never stopped talking. We chatted and laughed a lot, and it seemed to me that chances for a third date were good.

Then in the middle of dessert, she said: "You know why I'm here right?"

I didn't know.

Then she pulled out a binder and explained to me how she could help turn my life around as my financial planner.

I don't remember much of what happened next, except for making my excuses and getting the hell out of there. But it goes to show that not everyone is on Tinder for dates or hook-ups. Some are looking for customers.

3) Instagram date

- Yet another mysterious female Mothership staff

We met on Tinder and chatted for about a week, where we shared about our interests/ hobbies etc.

I told him that I enjoyed going to museums during my free time, and there was an upcoming exhibition that I really wanted to check out.

He told me that he was a museum enthusiast too (lol), so we agreed to meet for a first date at the National Gallery.

Omg when we went there, he really showed zero interest in the pieces.

He would just keep walking without letting me stop to read the explanations or admire the piece.

Worst part was when he kept asking me to take Instagram shots of him (not just one, but like multiple takes and poses at different art installations).

He even had the cheek to insinuate that my photography sucked and made me go up and down the stairs to retake the photo for him hahahahaha.

Towards the end of the date, as I was finishing up with the gallery, he just sat at the bench behind to edit the photos and uploaded the photo as we left the museum.

Of course he had to remind me to like the photo too sigh.

Never went out with him again :/

4) Two and a half years... of emails

- A female Mothership staff 

When I was still in school, most of the guys that I got close to were on bickering terms with me at first.

So there was this one whom I first started arguing with on the plane ride back from a community service trip we took to Thailand.

This was at the end of the year, and as we started talking to each other more and got close (those days we used MSN hurhur), I waited for him to make his move.

Over Valentine's Day he gave me chocolates (my first box of Royce! I will always remember it haha) and a nice letter, but for some reason, he never asked me out.

I then tried to initiate it (you know, feminism, gender equality) but he told me he should be the one to ask.

So I waited.

I can't remember what happened after that — seems like we lapsed into an awkward silence — but around five months later I think he finally got the gumption to ask me if we could "take things up a notch".

Unfortunately by this point, I, uh, may have already started talking to I dunno, two or three other guys, thinking this fella wasn't ever going to step up, and so I guess you can say I had already emotionally "moved on" from him.

But this would be the beginning of what would go on for... about two and a half years of emails.

After awhile I gave up responding to push him away — and I did, actually, pretty harshly in the middle of the year.

In response, he claimed he was an introvert and it was difficult for him to express his feelings clearly to me — I'm sorry, but too bad?

In these emails, he also told me that he loved me (even though a "staggering" number of people told him I wasn't worth it and that I was a horrible person), he would wait for me, I didn't have to do anything, he wouldn't take up my time (but really, what relationship is that geesh).

All this being even though I had, by the end of that year, gotten into a relationship (an actual one).

I can't remember if I had told him that I was in a relationship by this point, but I do recall that in one of the last emails he would send me, he pasted the lyrics to Toto's "Africa" (I'll leave you to check them out if you don't know it).

Thankfully, after those years he perhaps got busy with his life, and is now married to a nice girl I know (and I think has a kid too!) and a doctor in the U.S..

I dropped him a message to congratulate him (one on his residency too, actually), and both were ignored, so I guess all's good between us now hahaha. And I am genuinely happy for him.

But I've gotta admit, I will never see "Africa" the same way again.

5) NC16

- Female Mothership staff, "Anonymous pls!!"

I was walking around the Joo Chiat estate with a guy I was dating at that time.

We chanced upon an abandoned (or under construction?) house with a loose gate latch, and as stupid 19-year-olds, decided to go in to... hanky-panky lolol.

We were at the patio/ front part of the house. Anyway, halfway through, I saw a rat run across the space and I screamed.

My scream startled him, which made him get up (reflex move? I'm not sure but maybe he wanted to run or something haha).

Unfortunately, because his pants were down, he tripped.

He sustained some scratches on his arms, but it was nothing serious.

I felt so bad. Now every time I see an abandoned house I think of that incident lol.

6) Is it some wrestling move?

I was in Secondary 3.

He's not an ex, but it was a date I guess.

The guy was in the same cohort as me, but we were in different classes. However, we talked quite a bit because we were councillors.

One day, he asked me to go for morning walk with him (we lived near each other).

I usually prefer older guys but I thought, walk walk ok la I go cause he nice also.

So I got up at 6.30am and went for a walk with him at waterfront park. It's usually romantic if you like the person.

There's this part of the park where you can see Malaysia from, and there were a few benches around.

We sat down at one of the benches.

It was damn awkward because I didn't know what to say to him??

SUDDENLY and with no warning he grabbed my waist, lifted me, and made me sit on his lap...?????

Like hello what do I do now?? And we were the same height? So now I'm taller than him on his lap and it's so uncomfortable like physically and emotionally??????

I didn't know how to tell him that it felt weird and I wanted to leave.

I think we sat like that without talking for 30mins? Or maybe it was five but it felt like 30.

Worst experience ever.

7) Not ok, Cupid

- Female Mothership staff, "ANON PLEASE THANK YOU!!"

I went on a date with this guy I met from OkCupid and it went very well.

In fact, I was very happy and excited, and wanted to see him again.

BUT THEN I did a bit of social media sleuthing and found out he was engaged and ABOUT TO GET MARRIED LIAO??!?!?!  To his girlfriend of seven/eight years?!?!?

And the thing is, he was even talking about his horror dates with other girls from OKC and how he didn't want to get married because it was too much of a commitment.

Anyway, he ghosted me before I had a chance to confront him.

It was damn traumatic and I felt so so so super bad ok. WTF cheating men/women/people y'all eat cockroach and die thanks.

Bonus story: Superhuman perseverance

- A real person (male)

Editor's note: Get a cup of tea, this is a long story. 

A girl I chased for five years rejected me thrice.

Let's call her Samantha.

I was 17 and in my first day of JC when I first saw Samantha in the canteen (before we were sorted into classes).

I had one of those movie moments where Samantha seemed to be walking in slow motion. She could've been digging her nose for all I care but I thought she was one of the cutest girls I've ever seen.

Through the haze of memory I remember she had one of those Harry Potter-esque glasses which made her eyes doubly big.

By sheer luck, we got put into the same class the next day.

I was (still am) the introverted sort who didn't make an effort to gel in with the crowd, preferring to eat alone during break times.

Samantha took the initiative to sit with me one day and hung out with me. That left a huge impression.

The thing is, even though she made the effort to talk to me, I didn't really muster the courage to interact more with her.

Coming from a neighbourhood school and now surrounded by classmates who came from schools with "posh" English made me feel like the odd one out.

I was awkward and it was such a daunting task to not sound stupid in front of the girl you like. I also felt that it would be too conspicuous for an introvert like me to pay special attention to one girl.

However, Valentine's Day was coming up and all the guys in class were talking about finding a date.

Armed with zero experience of chasing girls and feeling pressured to do something, I had to act.

I promptly SMS-ed Samantha on the eve of Vday that I had a crush on her.

She said she saw us as friends.

Cool thing was, she didn't really avoid me because of that.

March rushed by and we went to different JCs.

We didn't really keep in touch after that, and I moved on with life.

A few months later, Samantha found me on IRC (Internet Relay Chat, an online messaging platform popular in the 90s/early 2000s) because I was dumb enough to use my email address.

We started chatting very regularly on IRC and I found myself very attracted to her. At least the 'her' behind the computer screen.

Throughout these months, I've been talking about my feelings for her with my friend (let's call him Idiot).

Idiot decided that he had enough of my whining and pining -- he found Samantha on IRC and told her that I've got a major crush on her.

Awkward messages between me and Samantha ensued.

And the conclusion was she still saw me as a friend, which I completely understand because all I've done so far was chat with her online.

But I still thought we could be more.

We met up to study together a few times to prepare for our JC1 exams, and after the exams I asked her out for a movie.

It was a non-event. Looking back, the signs were there that she truly saw me as a friend, but I was living too much in my head to see otherwise.

JC2 arrived and we continued with our IRC chats.

Again, Vday was around the corner, and I thought I should make a grand gesture to let my feelings be known.

I bought this cookie jar, folded hearts to fill it up and put a Feb. 14 Beanie Baby in there. I asked her to meet me at Heeren after school on Feb. 14.

She said okay. Or did she say that she will let me know again? I can't really recall.

All I know is that I waited at Heeren for a few hours that day and texted and tried calling her.

But there was no response.

That night when I texted to ask if she was all right (I thought she might have passed out or something), she replied and apologised saying that she had switched her phone off because someone pesky had been calling her.

Operations confession Vday V2 failed.

But I wouldn't say my interest in Samantha cooled off after that.

We still had very enjoyable IRC chats, talking about life, celebrities, and music. She expanded my horizons by quite a margin.

She lived in a different world from mine and it was nice that she was sharing it with me.

We met a few times to study as the A-level exams were nearing, but I think we were both focused on the exams, she more than me.

Nothing much happened and it was off to NS for me.

We kept in sparse contact after that, as I was busy with BMT (Basic Military Training) and she was waiting to go to university.

When I was posted to my unit and had to work late nights, she offered to keep me company by texting me.

She was probably being a good friend, but that made me like her even more.

Determined to pursue her, I asked her out. We went out a couple of times during my bookout days, hanging around the Orchard area and catching a few movies.

Again, being a total noob, I didn't exactly know how to pursue her. We were just hanging out as friends then, no flowers, no expensive gifts.

And again, I thought it was a good idea to tell her how I felt about her over SMS after one of our outings.

But this time round, she said she felt the same!


But it was not meant to be. The memory of the next two weeks was a haze.

We didn't actually go out after that SMS. She had just begun school and I had to be in camp longer than usual.

After almost three years, this girl I have held a torch for finally showed interest. I didn't know how to act. I started writing long-ass emails to her trying to figure out whether we were a couple.

Yes, I know, I did not ask her to be my girlfriend officially in person so I shouldn't be expecting her to commit to being my girlfriend OVER EMAIL.

This was the pre-Internet era and there was no instruction manual to winning a girl's heart, ok?

Needless to say I messed up by being overly needy and totally weirding her out.

She said school was starting and she didn't think dating would be a good idea.

We stopped contacting each other after that.

Subsequently, in university, I joined two orientation camps and that's where I met J.

She was a year older than me, and I mustered the courage to approach her only after my camp mates told me she found me cute.

Long story short, we went out a few times, and even held hands.

One fine day, a good buddy of mine, Well-connected Bro, told me that J was actually attached.


Bummed out, I did what most emo people of my time did: Updating my MSN status to something emo. And I cut off contact with J.

After close to a year of not being in contact since NS, Samantha messaged me about my MSN status. Turns out something similar happened to her around the same time.

And with that, we reconnected.

We spent time studying together and hanging out again.

It was back to the days of us just spending hours talking about the quotidian.

Being five years older than the first time we met, I'd like to think we've both grown a little. In some way, she has shaped part of my world view on things and how I am as a person.

It was such a joy to talk to her and hang out. Unfortunately, I started to catch feelings for her again. (Future me: You blooming idiot)

It was towards the end of her final exams of her last semester that I expressed my feelings again (bad timing I know).

This time I did it in person. No more stupid SMSes.

However, she said she wanted to focus on her final papers first.

Alas, two weeks later on the day of my last paper when I went to meet my friend, Well-connected Bro, he told me that Samantha was attached.

That was quite a blow. I texted her to ask why she did not tell me she was attached.

Her response was that she didn't see the need to announce it if I did not ask.

I cried on my bus ride home. And that was that.

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Top image via Destini IS