Confessions: What was your worst one night stand?

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Remember when you were a kid and you used to go to the shop on a Friday with your mum to stock up on Mizz and Bliss and Sugar? The best things about those glorious pre-teen mags were the “cringe” confessions pages. Where everyone could post totally completely true stories about the “lush lads”, the “crushes”, the cringe moments when they fell over – oh my god – in front of the whole assembly hall. Once you reach your twenties, you don’t have the equivalent safe space to talk about all your mortifying moments. We’d like to amend that. In our confessions series, you can bring back the halcyon days of being 12-15, but you know better because you’re much cooler and more put together now and that.

We started by asking people about their worst one night stand experiences:


It was Freshers’ Week, and a second year (an older man) approached me on the dancefloor, and we sloppily kissed the night away to various Avicii and Katy Perry songs. As the night wore on, we somehow ended up back at his glamorous house, and in his bed – which was a mattress on the floor. As the drunken fumbling began and he got up to go to the loo, I noticed something… he had “Wild Boiz” tattooed on his arse cheek. I, quite generously, laughed and asked if it had been a drunken mistake, and he informed me, deadpan, that it was very serious.

For some reason this, or the fact he didn’t have a bed frame, didn’t make me jump up and run home. We went on to have incredibly lacklustre sex when he came back, after which two of his housemates barged in and sat on the end of his “bed” asking him how I had been and commented on my tits. For some reason, the “compliment” didn’t placate me, perhaps because they didn’t talk TO me once, only about me. He was not bothered and I was mortified, but I couldn’t get up and leave without exposing myself to everyone there. So I had to stay and listen to their terrible chat until they got bored and my prince charming had fallen asleep. Until I crept out at 5am that is.


It was New Year’s eve and I’d bought new clothes, so I thought I was cutting quite a dashing figure, but the reality was I’d drunk seven Jägerbombs and was shouting the word “dickhead” at my friend James for reasons I can’t remember. That was the taxi. Then I was in a kitchen (can’t remember whose) holding a big bottle of prosecco (not mine) and I was sharing it with a girl called Jennifer. She was telling me she was the year below me at uni, doing the same course, and I was doing that glazed eyes listening but not really listening thing, so I asked Jennifer if she wanted to go upstairs. She did.

We went up, and I was holding orange juice now as well and Jennifer was saying something about Prince Harry. In someone’s parents’ room and Jennifer was now on top of me and pressing her (large) breasts into my face. Hard. Really hard. So hard I had a nosebleed. All over her breasts, all over the (inevitably) cream carpet. That was when the owners of the house came back. I recall them screaming the words “what”, “the”, “fuck”, “are”, “you”, “doing”, “in” and “here” at me and Jennifer quite a few times. As I left I kicked the orange juice (probably an accident) all over the carpet, which now resembled some kind of crime scene.

Smash cut to March, the new clothes are old and I haven’t seen or spoken to Jennifer since NYE. I’m wandering around a club looking for a bottle of water and then Jennifer is in front of me and my inner monologue is like how Fernando Torres’ must have been when he had that one on one against Barcelona in the CL “shiiiiiiiiiiiiiiit”. But you know what? Jennifer was pretty safe about the nosebleed. So like Fernando, I scored.

Jennifer and I had sort of OK sex back at her place. We lay there in that blue grey not quite morning light and we talked. Jennifer said she thought I looked like Prince Harry (which is generous). And the blue grey light changed and soon the rest of the room was visible, the clothes on the floor, the photos of Jennifer and her friends on the walls, the keep calm and carry on poster… the pictures of Prince Harry and Prince William and Princess Diana on the wall, the literal shrine to the Royal Family on the wall, the SHRINE devoted to Prince Harry on the wall. I felt like a voodoo doll. I was some kind of shag a royal fantasy boy. I was creeped out then and I’m creeped out now. My skin didn’t crawl, it ran. I left and on the way back to my flat it rained. I didn’t have a coat.


I met him in the smoking area of my hometown’s grimiest pub. He was going to be my exotic new fling – he was a couple of years older than me, had a neuroscience degree and was a bit too cool to appreciate the repetitive R & B like the rest of us. He took me back to his (he owned his own house) and we had sex. It was good. But when I woke up in the morning he wasn’t in bed. I wandered around the house for him and came across a young girl’s bedroom. Turns out it was his four-year-old daughter, turns out she was also called Grace.


When you meet a fit DJ who wears cord Ralphies you’d be stupid not to try. I pulled him, but he was very hot and cold. Very hot when his mates weren’t there, cold when they were around. He came to another club with me and my friends and things got steamy. He came back to mine (it took a while to get there) and I was very excited. I got him in my room, got him near the bed, took every single item of clothing off before he said “I’m really sorry, I’m seeing someone”. I put my dressing gown on and let him out. I should have seen the signs.


Tonight, I was destined to pull. It was one of those nights, and by 2am I was ready to take anything. I was out of options. We made a quick loo stop in the pub opposite the club and I found a 4/10. On the way to the loo, we hooked eyes and there it was, two solid minutes of empty conversation and I was abandoning the group for a quickie in a flash Stoke Newie house. It lasted 5 mins. He came, but as he pulled off his soggy condom he exhaled “finish yourself off”. I didn’t. He rolled over, fell asleep so I let myself out and waited for an Uber. I never even asked his name.


Ibiza 2012. I met Dan at the Zoo Project and from then I was pretty obsessed. So when him and his mates came out with us at the end of the holiday, and then we shagged, I was on top of the world. I was even contemplating messaging him when we got back home. The next day on the beach however, I was strolling into the sea, I noticed something strange in my knickers. I got into the water and pulled out a condom from the night before, come and all. Cringe.


There’s a finite number of pubs in my hometown. There’s a finite number of combinations in which to visit them. No wonder then that the occupants of said pubs resort to fighting or fucking each other on a weekly basis to alleviate the tedium. What’s odd about this story is that we started with the former in a kebab shop, instead of a pub, and finished with the latter at my house, instead of a pub. Apparently she was a kickboxing black belt, half Irish, half Scottish and half Polish. I don’t remember the sex, only how unattractive she was and that I wore two condoms. She was gone in the morning before I woke up. I probably would have forgotten the entire thing if it weren’t for the fact her name was an carbon copy of a recent third round FA cup tie.


Sexual experiences abroad are exotic, adventurous and the making of dreams. Wrong. I found myself in a gay bar in the depths of the Irish countryside, when a quite attractive, not normally my type comes over. After some grinding to Girls Aloud and one too many vodka tonics, we go back to his. He’s just split up with his boyfriend so there was some sad talking, but soon we went upstairs and he goes down on me. It’s a bit teethy. He starts retching and the next minute he’s sick all over my stomach. It was really red.

Then he starts horrifically crying and asked if I’d stay and hold him. I said no, got dressed and didn’t look behind as I left.


I had met him the year before at his house party, and we saw each other in the smoking area of a club. I had broken my nose a couple of months previously and as we were getting together he kept on bumping into my nose, causing me a lot of pain. We got back to mine and while I was in the bathroom he opened the bottle of red wine that my mum had given me as a movin-in gift. I walked in as he was downing it from the bottle, to which I asked what he was doing. This should have been an early warning sign.

He then proceeded to spill the red wine all over my bed and floor. Later he got out a cigarette to light in my room. None of my housemates smoked so I said we had to go outside. At this stage he put on all his clothes and his shoes and we went out to my garden. He said he was going in to get a glass of water and I then heard the front door on the other side of the house slam. I walked to the front of the house and he was nowhere to be seen.

Fast forward 24 hours and he runs up to me in a club and insists he buys me a drink. At first I declined but he was persistent, and went on to tell me he had taken some things from my house but would not tell me what. I came to deduce later that this was my dental retainer (£150 replacement, he never admitted it). He told me he had been hiding behind a car when I was saying “hello?” out of the front of my house, and that he “didn’t really know why” he was did it.

He then insisted on cooking me and my house dinner, to which I firmly declined, but the following day he arrived with his friend to “see if we needed anything, like pans or chairs”. He then left, before messaging saying that he’d “had a better offer” but that he’d “make me a doggy bag”.

I saw him again two days later and he bounded up to hug me. I did a sharp 180 degree turn and he followed after me and said: “I can just never work out whether you hate me or not”. He lived less than 20 metres from me and – this having happened in week two – I spent the remainder of the year in fear of bumping into him.


It had been a dry eight months, and things were getting pretty desperate. It was the start of summer, just at the end of second year. My other friend, who was also experiencing a bit of a dry spell, decided we were going to have a mad one. This was it, we’d had enough and we were going to pull if it was the last we did. We hit Heebies and we were in our element. Bums were out, lashes were on and half an hour in, we were already being chatted up. Result. My friend had bumped into an old booty call – a sure fire shag. I was left chatting to a group of guys and the conversation was flowing. He was a typical “nice” guy, and as the vodkas went back, I convinced myself this was the sort of guy I needed to be pulling. No more rugby boys, no more idiots who wouldn’t even remember my name, finally I’d found a nice boy who was definitely punching and therefore would definitely shag me.

Things started to get weird. He was getting a bit clingy and even followed me to the loo. My friend’s booty call had a very, very fit friend. He was 6’6, played rugby, and openly said all he wanted to do was shag me. But taking the moral high ground, I drunkenly told him I’d had enough of his type and was going to take home the lovely boy who was following me round like a puppy.

I order a cab, and we clamber in. This was it. This was actually happening. Eight months of failure and I’d finally sunk so low it couldn’t go wrong. Until he passed out in the cab. We pull up at mine and I tell the taxi to carry on and drop him back off at his. Except he’s not from Liverpool, he’s visiting for the weekend and is too smashed to remember what hotel he’s staying in. After bickering in the cab for 10 minutes, I cut my losses and tell him he can sleep on my sofa. He climbs into my bed and passes out. I reluctantly get in, and instantly he’s smothering me, trying to spoon. “I really like you, I really really like you. I’m so sorry I can’t sleep with you. Can we go on a date?” I want to vom. He eventually falls asleep and I resign myself to eight more months of not shagging. I wake up at 7am and call him a cab – he needs to get out. He finally leaves and that’s when I realise I’d made my worst mistake my giving him my number the night before. Two minutes later: “I miss you already”. I still get invited to his “surprise birthday party” every year.


After a less than painful break up with an ex, in part due to a mild crush on his childhood friend who was at university with him, I decided to get some revenge. It was almost a personal challenge, but was also a bit of rebound fun. I was in sixth form, and one day my friend messaged the childhood-now-university friend with something flirty. Being one against lamely admitting a frape, I went along with it until I was on the train back up to the university my ex was also at. I met his friend, who was pretty fit, and one thing led to another until we were naked. Horrified, it was difficult to take my eyes away from his waxed private parts, but it was worth it for the face (I told myself). After a few quick thrusts, lasting all of LITERALLY 30 seconds, he came. When I looked at him, both shocked and looking for an explanation, he said, shrugging: “My hips are tired.” I have never been so aghast. No sexual experience has even come close to how bad it was, and how much I regretted it after. What a waste of a train fare.


I was out one night with my housemate and her gorgeous friend from home, who I’d had my eye on for a while. It was a great night, the drinks were flowing and, much to my luck, one thing led to another. We ended up in bed together, having great sex – or so I thought.

The next day, after she’d left in an awkward hurry, I was at a barbecue with a fair amount of people I knew. I was gushing about how good the night before was to a couple of my friends when I noticed a bit of an odd look cross my flatmate’s face. Instead of ignoring it, I decided to ask: “What?”

“Well…” she said, nervously glancing across the faces of the now-hushed group: “…it doesn’t matter.” Not realising she was trying to spare my shame, I pushed further: “No, seriously what?”

“Well it’s just… she said you smiled. The whole time.”

The blood drained from my face as an entire garden’s worth of people collapsed into laughter. All I could picture was my (admittedly wide) grin bobbing over this terrifed girl, like some kind of haunted Jack-o-Lantern. It looked as if I’d enjoyed myself, but perhaps a bit too much. Needless to say, we never slept together again.


The earliest warning sign should have been her chat up line. Jabbing me with her finger, she pointed at her own face and said in a thick Essex accent: “Who do I look like?” The answer she was looking for, apparently, was Stacey Solomon. A few hours later and we’re walking back to hers. It’s beginning to spit with rain.

Things started fine, pretty much like most tipsy one-night stands. As things began to escalate, she made an excuse to go to the bathroom. It took a few minutes to decide on the appropriate level of nakedness to be in on her return but after 10 minutes I thought I should probably check if she’s OK.

When I got to the bathroom, the door was locked. The light, on. I knocked: no answer. I returned to the bedroom, put some clothes back on. Looked out the window. The rain was now torrential. Home was 20 minutes away. I had no phone battery left to call a taxi. Faced with an impossible situation, I took an incredibly ungentlemanly decision.

“Hope you’re okay. Unlock the door and I’ll get you some water.” I wrote it on a piece of paper found on the girl’s desk, slipped it under the bathroom door and waited a few minutes. When the door stayed locked, I went to her room, got into bed and fell asleep.

A few hours later I’m woken by the door opening. It’s her. I make a move to get up but she pins me down with a surprising level of strength, strips completely and the most excruciating 20 minutes of my life began. To this day I’ve never met anyone else who has a “don’t touch me with your hands or mouth below my waist” policy. It was bizarre and I wouldn’t recommend it to anyone.

When it was over, I got up to leave but she grabbed my arm and said no. She pulled me back into bed, only to roll over and go back to sleep within minutes. Awkwardly, I lied there a bit longer, trying to figure out whether it was worth staying. Eventually I tried again. This time she said no but I ignored her. Besides, it had stopped raining now. As an act of goodwill I wrote my phone number on a pad on her desk. She asked what I was doing and then laughed when I told her.

Two weeks later, I’m back stood outside the same club chatting to some friends when over my shoulder I hear it again. “Oi, who do I look like?” Poor bloke.


I’d been dating a girl but then things ended. A month later I got a call from her asking to go for a drink, I said I wasn’t going to as it was a SUNDAY. Six hours later she tells me she’s outside my flat, so I went out but she’s not there or anywhere near where the bus stop she said she was at. It turns out, after a frantic half hour getting her to send me her location on whatsapp, she was at a bus stop on the other side of London. And, she’d fallen asleep so I had no idea whether she’d still be there. Having told her friends she was home, I was the only person who knew where she was.

I found her at a bus stop, 45 minutes away. At 11:30pm on a Sunday, I picked her up, took her home and fell asleep leaving her to sober up. I was woken up again at 5am. She’s fine now but crying, so we chat for a while, then she gets horny so we start to have sex. Next thing I know, sneaky anal. Nothing up my posteria but I realise I’m not where I normally am, I’m in the wrong place, and because I was sleepy, had no idea.