Weird Online Dating Encounters

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Source: Tofukicks

You know those weird ads that appear on a lot of sites you visit? The ones’ advertising, “Horny Moms in Your Area” or something similar?

Well, when I was still a single, bored and curious guy, I decided to create accounts for these dating sites and see what it’d get me.

And boy, do I have a ton of weird and disturbing encounters to share. (And no, I am not making any of this up).

Twisted Fetish

The whole idea of messing around with these dating sites, was just me expecting to talk dirty with chatbots.

But eventually, I met a girl – let’s call her Vivian – who for some reason, was using a site whose slogan was, “hookups-guaranteed” to find her soulmate.

That didn’t stop me from trying to make a move on her, and soon we even traded Instagram accounts to chat with each other. Luckily for me, Vivian was an actual human.

Two weeks into our chats, I decided I had played the long game long enough and asked her out.

Calling for a game of truth or dare, I planned to dare her into going on a date with me (cheesy, I know, but I’m 18, and this happened very recently when I still had limited dating experience).

Back and forth we went daring and asking questions about each other and just having a good time. But the next dare was where it all went south.

Daring her to tell me her fetish, it took her a minute or two before replying.

“I want to sniff your toenails.” was what she replied.

I was expecting a normal but deeply-hidden answer – like BDSM, or being tied up, or anal. You know, normal. But nope, it had to be toenails.

After a moment of feeling my skin crawl, I asked her if she was joking but she wasn’t. And to prove that she wasn’t lying (I didn’t ask for proof), she decided to send me a video of herself sniffing her own toenail clippings.

Anybody else feels like they need a bath now?

Multi-racial Gang Bang


Believe it or not, there was an actual “gorgeous blonde” in my area!

On a month-long modelling trip around Malaysia, I managed to match with a Ukrainian on Bumble while passing through town.

Instantly, we hit it off (she was even ok with me being younger than her!). She also wasn’t hesitant to admit that only wanted to fulfil one of her “sexual conquests”.

And me, letting my alpha-male instincts do the thinking, agreed to everything. But like every human ever, I forgot to ask for the terms & conditions to her desire.

Again, I was expecting something normal, but god forbid me from having a normal one night stand and popping my cherry. No, instead she wanted to have a “taste of everything at once”.

Confused, I asked her what she meant. She answered by saying she’s read about the diverse races that inhabit Malaysia and would love to sleep with all of them… at once.

My frozen expression and jaw being half-dropped made her chuckle. Before I could even reply, her eyes glistened up and exclaimed, “I already have a Chinese guy (felt insulted by how she pointed at me) – now I just need an Indian, a Malay, and an Orang Asal.” (But I respected the fact that she did her research and new the difference)

Realising this woman was looking to reenact something straight out of Brazzers, I did the only sensible thing and backed off.

Sure, the prospect of sleeping with a Slavic woman sounded like a once-in-a-lifetime opportunity, but I wasn’t prepared to lose my virginity in the same room with three other random strangers.

Double Catfish


When I was sixteen (don’t call the police yet, hear me out), I had already toyed around some cheap-dating sites. I was just really curious but wasn’t actually looking for anything.

On a site which advertised, “singles in your area”, I decided to create a spoof account as a woman to see if any guys would actually hit me up.

And I went all out on this account – I wrote a very nice bio about how I loved to cook, and even stated what kind of guy I was interested in. All that was missing was a profile picture, but honestly, I wasn’t expecting anything out of this – I just wanted to look at the single ladies on this site (I was a very complicated adolescent).

But hot damn, all of a sudden a guy was actually interested in me. Chatting me up, he wanted to know more about me and, hoping that if he were lucky enough, get a picture of me (I was peeing my pants at this moment).

And doing the sensible thing, I decided to play along with this false identity and teased the heck out of this guy.

As the weeks went by, we got comfy talking to each other and shared our daily experiences – in a way, this was a very happy (but weird) relationship I had fabricated. And things were about to get weirder.

Ultimately, he was getting really impatient and just told me that he had this dream of us in a threesome and he wanted to make that dream a reality (even though he never saw my face).

Playing along, I asked him who would the other person be. It took him quite a while to reply. I started to think that I was getting in too deep and should just confess that I was an underage guy messing around (I mean, he wasn’t exactly looking for Juliet either).

Before I could write out my confession, “he” started sending messages consisting of long LOLs and laughing emojis before stating that I was catfished and that “he” was actually a “she” that was pranking me.

But I got the last laugh when I told her that the “female” that she’d been catfishing was actually a male catfishing her.

In an instant, the chat box froze and she just left the conversation. Like all the other women I’ve encountered, I never heard from her again.

I feel guilty now, but back then I was sixteen and a total loser who just got massively rejected, so this was a great way to distract myself from going into self-loathing.

Of course, since then I’ve experienced normal encounters or chat conversations with Tinder matches that just went nowhere, but these were some nights I remember vividly.

For more articles on dating, read Worst Dates Series: Horror Date in Thailand, and Worst Dates Series: Horror Set-Up by a Friend.

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Gregory Wong
An aspiring writer from Kuching. Opinionative, cynical, always hungry (figuratively and literally), and always searching for more meaning in life.
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