Online dating stories – how it all went wrong or perfectly right

by Natalie Lim

With the ongoing pandemic, online dating has become prevalent in today’s society. Most of us dream of meeting a stranger on the internet, falling in love, and riding off into the sunset with our “forever”. However, the reality is that relationships are hard to form and that dream will remain a fantasy if you’re oblivious to social cues.

In this article, 8 Singaporeans shared with us about their online dating experiences and the lessons they learnt. Hopefully, this’ll steer you into a relationship and not a relationsh*t.

*Names have been changed to protect identities

The Bad

The dolphin trainer that got too excited

Online dating experiences 1

Story by Rebecca*

Sometime last year, I went on Tinder after a heartbreak. Most of the matches I had didn’t make it through the “talking phase”, but one, in particular, caught my attention. Jay* was a dolphin trainer and I was intrigued by his work. We chatted on the app for a while before moving on to another messaging platform.

We spent a few days talking and it turns out that we shared many common interests and hobbies. However, I did make it clear to him that I was still recovering from a heartbreak and at this point, I’d rather take things slow and get to know each other as friends first. After a week, we met up for our first date. The date itself was pretty okay and we mostly introduced ourselves — things only started to go downhill after.

We were walking back to the MRT station when Jay requested to send me home. He stays at the east, while I at the north. It was a sweet gesture, but it was only the first date and I was uncomfortable with the idea. However, he wouldn’t let it go and I compromised by allowing him to get on the train ride with me. 

On the train, Jay told me, “I’ve deleted Tinder for you already.”

I was shocked. I told Jay that it’s only the first date. Though I appreciated the gesture, I felt that he didn’t need to as there’s still a lot more to find out about a person you’ve just met on an online dating app. Jay shrugged it off and we used our phones in silence. 10 minutes later, Jay asked,

“What games do you have on your phone?”

I briefly browsed through my phone to show him the apps. That was when Jay took my phone and swiped to the page where Tinder was at. 

“Oh. You didn’t delete your app?” He questioned.

Again, I explained that it takes a lot for someone to commit, and that I wasn’t ready to delete the app on the first date. Jay then responded, “I mean. I deleted mine because I like you a lot. But if you’re not ready, I wouldn’t force you. I don’t encourage using it, though.”

An awkward silence filled the train cabin for the rest of the ride, and I was thankful that he didn’t follow me home. Jay initiated to fix a second date, but I was scared and reluctant. I explained to him that things were moving too fast and I didn’t want to rush it through. 2 hours after the date, Jay texted me,

“I told my mum about you 🙂 Don’t worry, she says that you’re pretty.” 

That freaked me out and I took it as a cue to ghost him. He was just a little too committed and ready for my liking. But it didn’t stop him from double-triple-quadruple texting me. When I didn’t respond, Jay would flood me with dolphin videos and pictures. And when that didn’t work, he would reply to my Instagram stories and react to his replies, just so that I could get a notification. 

To end things off properly, I sent him yet another explanation, stating why I felt uncomfortable. Jay sent me a long pagro text of how “his feelings and efforts aren’t reciprocated” and blocked me everywhere. A day later, he unblocked me to ask if “we could give things a final go.” When I didn’t reply, he blocked me again.

Needless to say, I won’t be looking at dolphins for a while now.

Lesson: No matter how attracted you are to a person, always remember to take things slow. Coming on too strong may make you seem possessive and the other person uncomfortable. Relationships should start with both parties being friends — that way, you’re able to grow your feelings organically.

She invaded my privacy by looking through my computer on the first date

Online dating experiences 2

Story by Junhao*

Casey* and I met on an online dating platform. Though we did not have much in common, she was persistent in meeting up and I caved in. I invited her over to my house with the intention of simply playing games and getting to know each other better. 

The conversation didn’t flow well during the physical meetup either, but what shocked me was when I went out of my room to get water for the both of us, I came back to her rummaging through the files on my computer. She was looking through my photos and asking questions like, “who is she?” 

I didn’t feel comfortable at all and was angry at the fact that she disrespected and invaded my privacy. Shortly after, I made up an excuse that I had something on so she had to leave. That was the last time I spoke to her.

Lesson: If the conversation doesn’t flow well through text messages, there’s no point in forcing it further. It’s normal to do a “background check” on the person you’re meeting up with, but invading their privacy by looking through their things? That’s a violative act — much more on the first date. 

My friend showed his genitals on his first virtual date and was blackmailed

Online dating experiences 3

Story by Kyler*

I know of a friend who’s quite “thirsty”. Through his social media’s activity, he’s always commenting on models/influencers’ photos. One day, he vanishes. He returns with a long post detailing a recent incident and wants to “spread awareness about it”.

Apparently, a girl found him through his comments on the pictures and sent him a Direct Message (DM). They start getting flirty (screenshots provided) and she initiated a video call. In the video call, the girl requested for him to masturbate. The moment it ends, she sends a text,


You reap what you sow, but here’s where it gets absurd. When he posted screenshots of the chat, he didn’t censor the part where his penis was shown. So in essence, he leaked the image out by himself — to the rest of his friends and family.

Regardless, he goes on to pay the $500 to get her to delete it. Of course, she doesn’t. She asks for another $300 at which he gives up and blocks her. 

Lesson: Sexual desire is human nature, but when meeting strangers from the internet, always be mindful of the content that’s exchanged — even in long-term relationships, you’ll never know if the tables will turn on you.

Fart on my face, please

Online dating experiences 4

Story by Jeanne*

I met Adam* on KikFriends. He’s from England and about my age. Looking back, I should have seen the signs when he used an overwhelming amount of emojis. It was like “????????????❤️????❣️????????????????????????????????❤️????????,” but more.

We were talking normally when suddenly, Adam asked,

“Can you fart on my face ????

I was horrified and thought it was meant as a joke. I refused his request. However, Adam kept pressing me on and I decided that this was the end of our conversation. Forever.

Lesson: It’s okay to have kinks but everyone has boundaries that you should not cross. Perhaps such kinks should be stated beforehand and not out of the blue. It’s not nice to force someone into doing something they do not want to either. 

The Good

He was from Malaysia, but he sent bubble tea to my office

Online dating experiences 5

Story by Laymian*

I met Alex* on an online dating app. Alex lives in Malaysia, was older than me by 3 years, and has a stable job. We’ve had decent conversations on the app, so we moved our chat to Telegram. Since then, we’ve texted back and forth and even had video calls. 

We’ve discussed about him coming over to Singapore to sightsee before. When he did, I brought him around and we talked for a very long time. Things hit off quite naturally, but he had to go back.

We were supposed to meet again, but I got busy with work. I couldn’t reply to Alex on time or as soon as I could. However, he stuck on and the next time I met him was 2 months later in Malaysia. He was very gentlemanly. He drove to the checkpoint to pick me up, and we went to his hangout places and even caught a movie together. We had dinner by the seaside and had a walk around his neighbourhood. I usually don’t stay out too late when overseas, but with Alex, I knew I was safe. I remember that while we were walking on the road, he slowly switched sides with me and made me walk at the inner side instead. Though I’ve never explicitly said it aloud, it was very sweet.

One day, I was stressed at work. We were talking about how I love drinking bubble tea when he asked what I’d usually drink. I told him my 2 favourite orders. The next thing I know, my colleagues told me that I have a delivery of 2 bubble teas. I didn’t suspect that it was Alex as he’s in Malaysia, until he messaged to ask if I’ve received it. 

Apparently, he got his Singaporean friend to send the bubble tea to me. We did chat for some time, but eventually parted ways amicably as we did not have the time to commit to a long-distance relationship. However, I was very touched by his actions and he gave me a clear picture of what I wanted in a relationship. To date, I think that he’s “the one that got away.” 

Lesson: At the end of the day, it’s the small actions and effort that make it work. Things may not have worked out for OP (original poster), but this journey helped her grow as a person and set better expectations for the next relationship ahead.

He sought approval from my friend before talking to me

Story by Geraldine*

I met Byron* on an online dating app and we hit it right off the bat. He had a sunshine personality and looked cute in his pictures. We texted back and forth for a few days, but I never had the time for a meetup. We were in the middle of a pandemic and as an insurance agent, it was a busy period and I met most of my clients through video calls. 

Byron knows of this and one afternoon, he requested if “he could have a bit of my time” and suggested a video call. I was with another colleague, but Byron said that he didn’t mind talking to him as well. 

When his camera loaded, I was greeted with the same sunshine vibes from his pictures. He had a beaming smile and what I described as “kind eyes”. But before speaking to me, he asked to see my friend first.

“Hi. I know you’re OP’s friend, can I have your permission to just steal her away for a little while? I promise that I’m not a creep.”

It was funny, but also adorable. The moment immediately granted Byron the green light from my friend. Though memorable, our conversations eventually fizzled out. I still think about Byron now and then, though.

Lesson: Respect always goes a long way. First impressions are important and they set the path of where the relationship is heading towards. If you screw that up, chances are, you won’t get another opportunity to re-present yourself.

We couldn’t meet because of Circuit Breaker, so we ordered surprise meals for each other

Story by Terrence*

I met this amazing girl on an online dating app during the first Circuit Breaker lockdown. She’s pretty, but it was her free spirit and the easy conversations we had that felt the most attractive. We were dying to see each other but since we couldn’t, we decided that our first “official date” would be held online. Instead of simply initiating a video call, she suggested that we should order a surprise meal for each other. That way, we’d be excited about our food and we can dine together.

The date was really nice. She was exactly what she portrayed herself to be through text messages, and there was no awkwardness at all. Perhaps, there’s something about getting to know somebody completely only via the internet and online interactions. It felt intimate and I really connected deeper than the typical “go on date, get smashed, then smash” route that online dates usually take.

AND, she had good taste — the ramen was delicious, so 11/10 for this girl. We did meet up after the lockdown and dated for a while. Unfortunately, we’ve parted ways as we had different ambitions. It was good while it lasted, though.

Lesson: Dining-in may be suspended for now, but all it takes is a little spontaneity and creativity to still have a good time. Most of us try to show our best sides on dating apps, but just being yourself is also a sort of beauty that no others can replicate. 

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I leave the office at 6PM on the . to rush home and play games. My boss has no control over me!!

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