50 Women Reveal The Raunchy Details Of Their Biggest Hookup Mistake Ever

19. Really creepy older guy

The guy I lost my virginity to. I met him when I was 13 and he was 20 – he was a family friend and I went to school with his younger brother. I harbored a huge, obsessive crush on him. I would fill journals talking about how much I “loved” him and wanted to be with him. For the most part he treated me like a little sister but there were times where I felt like he was flirting with me, and of course that got my hopes up. The main problem I saw wasn’t the age difference, it was the fact that he had a girlfriend.

Anyway, three years go by, I was 16 and he was 23. He and his girlfriend ended up breaking up and he randomly messaged me one day and told me about it. I was like “oh no, I’m so sorry to hear that” and he was basically saying “yeah, but it would make me feel better if there was someone I could have a secret rendezvous with” (he used those words lol). I had never even had my first kiss, but I saw this as my shot, like the thing that I’d been wanting for three years…. So I agreed, we hooked up, he kept pressuring me to go further and have actual sex. I didn’t really feel comfortable or ready but he told me that he loved me, he told me he wanted to “run away with me” so we could be together, shit like that (also, side note, I told him cheesy stuff like “oh I’ve wanted you for so long” and he told me that if I made a move on him back then he would have reciprocated…. which is FUCKING CREEPY AND DISGUSTING LOOKING BACK BECAUSE I WAS 13!!)…. So I eventually went with it. The very next day, he told me he was going to try to get back together with his ex. She turned him down.

Now he’s almost 30 and has nothing going for him in his life, so that makes me feel a bit better. I’m about to turn 22 and I just think it’s funny looking back, how I thought he was soooo mature and amazing and “our connection transcends age” and stuff like that, but now being that age, the idea of going for someone under 18 is physically nauseating to me.

— WildHoneyChild

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