Online dating is often a hit-or-miss affair. There is a lot of room for things to turn awry and… awkward. From terrible introductions to straight-up degrading comments, 9 Gen Z Singaporeans shared with us their most awkward Tinder and Instagram encounters.
Names have been changed to protect identities.
First of all, I was already extremely shooketh when he introduced himself by requesting for ‘leg pics’. It was sleazy AF.
But for some reason, I thought he was joking. So, I played along and sent him a photo I took during a sleepover—as a joke.
To my horror, he responded with, “I’m fucking horny rn”. That was the red flag, obviously. I bid farewell, and pursued the conversation no further.
I was partying at a club one night, when I noticed this cutie eyeing me from head to toe. We exchanged glances and engaged in small talk. By small talk, I mean, “Hi. You’re here with your friends?” to which I responded, “Yes.”
End of conversation.
I have no idea how he found my name or my Instagram account from our pathetic 2-line exchange, but I received a PM from him the following day with just ONE word: “Eat?” Mind you, I had no clue what his name was. There was no proper introduction and it wasn’t even a proper question. Hello? I’m not your dog.
He went from 100 to 0, just like that. Sad.
Literally, no one asked. Thanks, but no thanks. 10/10 awkward.
At first glance, I thought this was just some HR manager trying to use Tinder as a platform to boost recruitment. It took me a while to get it. Not gonna lie, this is by far the worst pick-up line yet.
Ladies, this is what happens when you turn down prideful men. Their ego gets tarnished, they feel vulnerable and insecure, and get defensive. I mean, ‘mystical cb’ sounds cool though.
You can continue talking to the ‘mystical cb’ that you will never get to lay your hands on— whether it’s me or any other lady, as a matter of fact.
I chanced upon this cute girl who, on her profile, encouraged guys to “hit her with the best pickup line you got”.
Now I’m a nice guy who hardly uses any pickup lines, so I went with the classic ‘cutecumber’ joke. Obviously, it didn’t work out. She told me to try harder. So I hit her with the dark arts.
She stopped talking to me afterwards.
After matching with this douchebag on Tinder, he texted me, “I’d gladly get catfished by you”. Thanks for implying that I’m pretty, but fuck you for accusing me of being a catfish. There is absolutely zero correlation between his message and my response, but my objective was to fight childish behaviour with an even more childish comeback.
He tried to pursue the conversation but I was over it.
I guess we might have matched by accident because I have absolutely zero recollection swiping right on this guy 2 years ago. But at the same time, I felt bad to unmatch him. So, I didn’t initiate a conversation. But he did.
He eventually turned sour when I didn’t respond to his texts with a sarcastic, “was a great talk!!”
What a loser.
Xin Yi, 19
To be honest, I thought he was pretty smooth, but then again, I didn’t ask. Bold of him to assume.
Needless to say, I stopped talking to him. Awkward.
If you’re actively socialising on online platforms like Tinder and Instagram, you’ll know that experiencing awkward encounters is par for the course. The choice to pursue the conversation is entirely up to you, but it’s important to remember to stand up for yourself and be honest.
However, if your match starts displaying inappropriate behaviour that makes you uncomfortable, stop interacting with them, and block and report their profiles immediately.
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