Worst Rejection Stories

Oh, to be young and feel love’s keen sting. Be it asking a cute stranger for their number or confessing your feelings to a long-time friend, it’s always nerve-wracking when you put yourself up for potential rejection.

While most people would politely turn down unreciprocated feelings, there are some less-than-kind individuals. From being laughed at to being called ugly, 8 Singaporean guys share their most painful rejection stories.

*Some names were changed to protect identities

1. Saw me as someone to sell insurance to

In Uni, I really liked this girl from my tutorial group. We were good friends and would hang out after school to study together.

During flu season, I caught a cold and missed a couple days of class. Concerned, she called to make sure I was okay. In a delirious state, I told her I liked her. She responded with an “Oh, okay… Uhm, get well soon!” and hung up.

When I returned to school the following week, she asked me out for a meal. Eager and excited, I agreed—I thought she was going to confess her feelings.

Instead, she admitted she saw me only as a potential insurance client and proceeded to sell me a financial plan.
Gabriel, 26

2. Asked her side guy to reject me

I was casually dating this girl. We weren’t exclusive but had agreed to tell the other if we were dating anyone else.

Gradually, my feelings for her grew stronger and I confessed to her. She gave a non-committal answer but agreed we should continue dating.

Turns out, she was dating another guy behind my back and was using me as her backup plan.

I only found out she didn’t like me when he came to my workplace and tried to pick a fight. He also told me to stop texting his girlfriend and to f*ck off from her life.
John, 21

3. Told me I was too ugly for her

When I was 15, I had a crush on the most popular girl in school. She was that girl, the one every boy had a crush on due to her sweet, girl-next-door vibe.

Because I was awkward and pudgy, I felt I didn’t stand a chance. Nevertheless, I mustered the courage to ask her out.

Scathingly, she looked me up and down and said, “A girl with a face like mine and a guy with a face like yours will never happen”.

I watched her saunter away, along with my desire to date her.
Paul, 25

4. Told me through an accidental phone call

When I was in Uni, I was paired up with the girl I liked to do a lab report.

The week before submission, an unexpected problem cropped up and I called her to discuss a solution. She repeatedly rejected my calls, but on the fourth try, the line went through.

From what I heard on her end, she was on a date and had accepted the call by mistake.

She was telling the guy how I, her lab partner, had the biggest crush on her and was the most annoying, repulsive, desperate person she’s ever met.

The last thing I heard was a guy laughing before the line abruptly cut. I finished the project on my own and never spoke to her again.
Qian Rong, 27

Also read:

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5. Rejected me after I brought her on holiday

There was this girl I’d been in love with for the longest time. We had previously dated but never explicitly ended the relationship.

When the year-end holiday period approached, I suggested we go on a 4D3N Bangkok vacation at my expense.

Throughout the trip, we held hands and behaved physically intimate with each other like any couple would.

Before our flight home, she told me she saw me as a good friend and that we should stop hanging out because she didn’t want me to get the wrong idea. The plane ride back to Singapore was the most awkward four hours of my life.

Now, she’s getting married and has applied for a BTO with her fiance. But if she ever asked to get back together with me, I’d agree in a heartbeat.
Xiaoming, 26

6. Dated my best friend 

I was in secondary school and we were classmates. I thought she was into me as we frequently hung out one-on-one.

Once, we secretly held hands at the back of the class when we were both being punished for not doing homework.

At the end of the lesson, I whispered I liked her. She smiled, let go of my hand, and returned to her seat.

The next day, I heard from the schoolyard grapevine she had gotten together with my best friend.

Rather than reject me face-to-face, she let the whole school tell me instead.
Jiarong, 22

7. Laughed in my face

I used to have this thing with my neighbour. On the weekends, we’d get ice-cream after dinner and hang out under our HDB block.

At the end of one late-night chill session, I decided I would confess and try to kiss him. As we were in the lift, I shyly asked if he wanted to give me my first kiss.

Immediately, he burst out laughing. In between fumbling for his house keys and trying to catch his breath, he managed to cough out a “no”.

Later that night, he texted me to apologise and told me I wasn’t the type of guy he’d want to fall in love with.

This was eight years ago and till this day, the episode still haunts me.
Brandon, 27

8. Told me she was in it only for the sex

In my first year of hall stay, I didn’t have many friends as I didn’t attend hall camp. I joined interhall softball as an extracurricular to get to know more people.

After one training, a girl came up and chatted with me. Over the course of a few months, we developed a close friendship which turned sexual.

Though everything was going great in the bedroom, she ignored me in public. Confused and miserable, I asked what was going on.

Unflinchingly, she said, “Listen, I’ll have sex with you but I don’t see us as anything more. If you can’t accept that, it’s best you move on”.
Fernando, 26

These Singaporean Guys Share Their Worst Rejection Stories

If you’ve ever been so cruelly rejected by someone, you’re probably better off dating someone else. After all, being with someone who treats your feelings so carelessly isn’t a good sign.

Relationships happen in good time, and eventually, you’ll surely find someone who’ll treasure you and treat you right!

This article was first published on 31 July 2017 and last updated on 16 March 2024.

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