We Asked People For Their Freakiest Dating Stories

I can’t decide whether dating is the best thing ever, or the absolute fucking pits. Perhaps I’ll never work that one out. It doesn’t matter anyway. Dating is inescapable. There are differences, of course, between first dates, second dates, hookups, “date night”, Tinder dates, and Hinge dates. They all smell different. But the premise is the same.

The fear and loathing inherent in linking up with a total stranger, is a universal sacrifice we make in the pursuit of whatever it is we’re looking for, whether it’s love or just a roiling good time. The latter can be – shocker – inanely difficult to find. 

But enough preamble. We know what we’re here for. 

My worst date found me making out with a soft art boy out the front of the Victorian State Library because I wasn’t yet sure whether I wanted to go home with him. His hands were on my chest, I’m thinking it’s a bit raunchy for Swanston Street. This was before I realised he was buttoning up my shirt, which had been tastefully – or so I’d thought – unbuttoned just low enough to reveal the hint of a lace bra. I asked him what the fuck he was doing, to which he replied, “Oh you don’t have to show so much skin”. 

In the godawful scope of things, that wasn’t even that bad. People are unhinged. 

Many wretched souls have had much worse experiences, and oftentimes the only consolation prize is the story. Here at VICE, we love stories. So I asked a few people to share some of theirs. 

I had a guy over at my place for the night and had a relatively okay time, besides the fact that he had PISSED THE BED and all over me during the night. I thought I had been sweating through the night until I realised what had happened, when I asked him if he had pissed the bed or not. He didn’t even act surprised, all he said was ‘oh fuck….’

We had to strip the bed and wash it all but I had to throw out my expensive mattress topper. I FOUND OUT LATER through mutuals that I was not the first offence and it had happened twice before that they knew of.

I went on a date with this guy a while ago and it was the WORST date ever. Here are some of the red flags I ignored.

• He didn’t have any money so I paid for everything.
• He was drinking 1 x whiskey AND 1 x beer in the amount of time it took me to drink 1 beer.
• We ran into some of his friends and he didn’t introduce them to me and proceeded to ignore me for two hours while they spoke and talked about real heavy shit that I couldn’t partake in the conversation about.
• He invited me back to do ketamine at his house. I said yes because at this point I NEEDED to as the date was going so poorly.
• When I turned down his request for sex he said ‘oh that’s ok I’ll just wank then’.
• He wanked while I just sat there in a K-hole.
• He fell asleep straight after he came and let out the biggest, grossest fart.
• I finally left, disgusted in him but mostly disgusted in myself for not leaving sooner.

There are so many. I went on five Hinge dates in seven days. Like, I think I’m actually the nightmare Hinge date for everyone else. The worst Hinge date was when I matched with this guy who I knew who wouldn’t like me and we had an argument over Hinge. Just to prove a point that we wouldn’t get along, I asked him out but instead he wanted to come to my house, where I had kicked down half of my bedroom door as a joke a few weeks prior. He came over and he spoke so softly and I was like pardon? the whole time because I couldn’t hear him. 

He was some model. The conversation was like pulling fucking teeth and then he asked to watch a movie and I said ‘ok what kind?’ And he goes ‘funny movie’ so I put on a psychological thriller instead because I fucking hated him. After like 30 minutes he went in for the kiss and he was doing this hell weird moaning and I’m like ‘no ok no’ and then I was like ‘ahh I’m like not gonna fuck you, you know that right?’ and he was like ‘should I go?’ I’m like ‘yeah lol?’. And he just sat there and I’m like ‘ok do you want me to walk you out’ and he's like ‘yeah..’ I’m like ‘ok..’ it was soooo bad lol.

And then he messaged me afterwards going off at me and I’m like ‘well I told you we wouldn't get along’, and I was right so yeah.

I got pretty shitfaced at a bar a few years ago and asked out the bartender who (through pinot coloured eyes) looked like a bit of a babe. He agreed, and we went to a local spot a few nights later. Jokes on sober me, he definitely wasn’t my cup of tea, but I digress. 

Not even five minutes in, he attempts to hold my hand across the table and stares DEEPLY into my eyes. He proceeds to tell me about how he’s been to jail for beating someone up. I start to get the red flag cogs turning, then after a few more drinks on his part, he asks if I want to go to the bar he works at. It’s on the way home and only a few doors down, so I agree, wanting to stay in public. 

It’s open mic night where he works, so he sits me down at a table close to the stage. He tells me he’s saying hi to a colleague so I wait for about five minutes and then I see him come up on stage, WITH A GUITAR HE’S PULLED OUT OF NOWHERE, sit on the stool and dedicate the next three, awfully sung love songs to me.

EVERYONE at the bar assumes it’s some really romantic cushy thing but it was just so fucking off and gross and I sat through it whilst he nearly cried a metre away, looking into my eyes singing ‘can’t help falling in love with you’. There are so many other bits and pieces from that night that I could mention, but that was a standout. He asked to stay at my house because it was too far from home, but it was one stop further on the train line. I completely ghosted him via text (the only contact he had) and he found me on all social media, so I blocked him. I found out a few weeks later that he was fired from his job for making non-cis het patrons uncomfortable.

The kicker is, he went to the same Dungeons and Dragons (DND) night as my current partner years back and it’s confirmed he never went to prison, and that he would often spit the dummy in DND campaigns. Maybe meeting in real life isn’t as romantic as it used to be, and instead we should be severely vetting online.

***Not a bad date, just a great story*** 

I got my Hinge date TikTok famous.

AND his colleagues called him the next day worried he didn’t know about it and that some crazy chick had made a video making fun of him. Multiple ex hook ups of his reached out to me. 

It started as a joke that since I’m six years younger than him, I’m such a Gen Z etcetera, and I warned him I’d make a TikTok about him. And then I think we were high and I was like ‘I’ve got an idea’, and just directed him and whipped it up in about five minutes. And that’s how I got my Hinge date TikTok famous.

I met up with a dude from Hinge who I’d been talking to for ages during the winter lockdown for a bike ride. We had a mild disagreement over whether we should ride to the beach or the park. He got really worked up about the conflict and suddenly rode away leaving me on my bike in the middle of the deserted south eastern suburbs of Melbourne. It was nighttime.

I met up with this dude at a nice little hawker style restaurant for a first date in Fitzroy. We sit down, have the usual introductory date chats and order some drinks and food. One of the dishes we ordered were these tamarind sticky lamb ribs – honestly delicious.

As I was reaching over to grab one of the little buggers, I see this guy reach for a napkin and begin smearing the rib on it and looking disgusted. Obviously shocked, I asked him what was wrong, and he began to go on a rant about how he’s on a keto diet at the moment and marinades like this have way too much sugar in them. He continued to tell me about his entire keto diet, including how much mayonnaise he had stockpiled in his fridge and how four years ago he had done the same thing and ‘gotten so shredded’.

So here I was, sitting across a fully grown 27-year-old man with sauce smattered across his mouth and fingers – MORTIFIED. He insisted he continue eating it even though, in his own words, the marinade was ‘so full of sugar’. I watched as he would wipe the marinade off each rib, tear at it with his teeth, get MORE marinade on his face and then try to wipe it and his grubby fingers off with an already sauce-soaked napkin, scrunch it up and drop it onto the table. It was giving George Costanza eating a chocolate sundae.

Safe to say once all the food was eaten and bill split, I never saw this man (child?) again.

I had one Tinder dude essentially not leave my house for two weeks and I was too [oblivious] to realise they were probably homeless and not in fact avoiding the Russian mafia.

I had to enlist help from my ex-bikie neighbour to actually get him to leave. He’d say his housemate was working with [the mafia] so he couldn’t be home while he was working then I’d say he had to leave first thing because I had work in the morning and he just WOULDN’T and I’d have to leave (first week at that job). Then, I’d come home 10 hours later and he would still be there!!! Pretending he’d slept all day when my housemates told me he’d been eating my food and popping down the road for fish and chips.

Then he got fired over the phone in front of me and called his dad to sook about it, it was so embarrassing. I finally got him to leave (admittedly after smoking a lot of his weed) and he stole my favourite shirt. Six months of no contact passes and he calls me up on Christmas Eve to say that he reckons it’s gonna be his ‘last day around’ cos the guys that gave him up gave up his family and all this crazy shit.

* many names have been changed

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