Dating and Relationships

My worst rejection

When I was 16 there was a boy that I was, to put it frankly, obsessed with. We had been in the same high school since the age of 11, but it wasn’t until Year 10 that we started having lessons together and my longing for him began. We became good friends, speaking every day…

April 6, 20220Comments ByAnonymous

“My worst…” Dating and Relationships

My worst morning after

We all know the feeling: head pounding, booze sweats and a delightful dose of hang-xiety kicking in. The morning after a night out is rarely fun, but none have been as bad as when I woke up in the bed of a work colleague. This is what happens when you blur the professional line, I…

April 5, 20220Comments ByAnonymous

“My worst…” Dating and Relationships Featured posts

My worst one-night stand

It was a normal Friday night in Oxford in March 2019. As usual, my flatmates and I decided to go out clubbing. This involved getting way too drunk in an attempt to forget life's troubles. I had just lost my virginity earlier that year and, for some reason, I thought that gave me some sort…

April 3, 20220Comments ByAnonymous

“My worst…” Dating and Relationships

My worst blow job

It was 2015 and I was at a friend's 16th birthday party — think plastic cups, girls in an assortment of flammable PrettyLittleThing dresses and a palpable ignorance to the effects of alcohol on the body. My ambition for the night was to “get some”. I didn’t care who or how, I just wanted some…

April 1, 20220Comments ByAnonymous

Dating and Relationships Relationships Advice Sex Talk to Prudence

Talk to Prudence – how to keep sex casual as a trans man?

Mystified by monogamy? Lost in the lingerie aisle? Confused by kinks or struggling with sex in general? Our resident agony aunt Prudence offers answers to PRUDE readers’ problems, to help direct and soothe, or at least make you laugh… Q. How do I have casual sex as a trans man? Bored of having whole ass…

March 31, 20220Comments ByAnonymous

Culture Dating and Relationships Featured posts

Are we all relationship therapists now? Gen Z’s toxic TikTok dating vocab

“Guys. It’s happened again.” A new message pings through on the text chain. “Oh God," is the first reply. “Not again,” says the next. This group chat of the seven girls occupying Number 3, Thornycroft Road in Liverpool documents everything you would expect to be the subject of discussion for a collection of 20-somethings living…

March 31, 20220Comments ByGracie Leader

“My worst…” Dating and Relationships Featured posts

My worst night out

I was writing moody short stories and living in a tiny house with six girls by the river in Exeter. She (let’s call her F) was living in the uni’s second fanciest halls and working on her Harry Potter Society presidency campaign. It was a classic love story. We’d been seeing each other for a…

March 30, 20220Comments ByAnonymous

Dating and Relationships Relationships Advice Talk to Prudence

Talk to prudence: all my friends have partners but I don’t

Mystified by monogamy? Lost in the lingerie aisle? Confused by kinks or struggling with sex in general? Our resident agony aunt Prudence offers answers to PRUDE readers’ problems, to help direct and soothe, or at least make you laugh… Q. I’m moving into my mid-twenties and suddenly all my friends have partners and it feels…

March 29, 20220Comments ByAnonymous

“My worst…” Dating and Relationships

My worst dick pic

They say a woman’s intuition is never wrong, but I believe a horny man’s is far superior. I’d barely thought of T for the past month, feeling vaguely pleased with his lack of interaction. I’d relaxed at the thought of his absence, relieved by his slow fading from my life. T seemed to possess clairvoyant…

March 29, 20220Comments ByAnonymous

“My worst…” Dating and Relationships

My worst holiday hookup

“I just wasted a condom.” That was the text I received after ditching my holiday hookup when things started to get a little bit… uncomfortable. A few hours earlier, I’d arrived at my hostel in the south of Brazil. As a solo traveller I was keen to make as many friends as possible, so I…

March 28, 20220Comments ByAnonymous

Sign Up to Our Newsletter