39 Shocking Confessions Reveal the Untold Truths of Hooking Up with a Friend’s Parent
Ever find yourself scrolling through a hookup app in a quiet little town and suddenly realize you’re about to hook up with someone who once drove you to school? Yeah, me neither—but apparently, it happens more than you’d think. When boredom meets charm (and a pinch of awkwardness), boundaries can get a bit blurry. These stories dive into the wild, weird, and sometimes surprisingly heartfelt experiences of people who found themselves entangled with a friend’s parent. It’s equal parts scandalous, funny, and downright human. So, buckle up and wonder—how exactly does one navigate the aftermath when your friend’s dad’s number pops up on your screen? <ahref="https://www.reddit.com/r/AskReddit/comments/lryi5j/seriouspeoplewhovehadsexwiththeir/gooieoq/”>LEARN MORE.
I slept with a childhood friend’s dad while visiting my hometown. Long story short he’s bi and divorced and I was browsing on a gay hookup app (it’s a small countryside town so the only things to do are ketamine, s*x or leave), he messages me and he clearly doesn’t recognise me because I don’t look the same as I did a decade ago. I recognise him and the entire time i’m thinking “this is really weird” but i’m bored and he’s relatively handsome and charming (as far as charming goes on Grindr lol) so I figure hey why not.
And hindsight is 20-20 because the s*x was fun but the entire time i’m thinking “this is my friend’s dad he has literally driven me to school before”. Just left an overall odd feeling.
My friend doesn’t know and it’s going to stay that way because we don’t really talk whatsoever now and it’d be weird to just pop up like “your dad jackhammered my prostate and it was kinda weird”.
Obvious throw away and I’m sure this will get buried but anyways.
Met this guy at the beginning of college. Dated all through college. Anyways my boyfriend at the time (the son) became super controlling, manipulative and borderline a*****e, which all came to a head when his parents years long divorce was finalized.
Dumped the boyfriend, he moved out of state and the dad still lived close by. Stayed in contact with the dad and many other people from his family. Eventually the dad asked how my dating life was an I took it as an opportunity to complain about how I was having a hard time finding people who I had sexual chemistry with. Turned into a conversation about kinks and eventually (over a few months) the tension just kept building. To be blunt. We were both h***y, lonely and knew the other person was into the same things so we started a fwb type relationship. Helped that the dad was young and aged wonderfully.
Eventually it ended, on good terms. We both met other people. We both pushed the other to date other people. Find something long term and more fulfilling then cheep s*x.
From what I know no one knows, I never told and he didn’t either. We were just lonely, needed some s*x and wasn’t about to have casual s*x with randoms. Might as well be someone you know that will be happy for you once you find the right relationship. Ya it was slutty of me and maybe I’ll regret it in the future but at the time it was amazing s*x with a good looking person I trusted.
And and FYI the dad never hit on me while I dated the son. To my knowledge anyways.
I had an on-and-off affair with my friend’s dad for almost 3 years. Started when I was 17 and he was… mid-40s, idk his exact age. Not proud of it. I’m a guy and he was married to a woman, so we kept it hush-hush for a lot of reasons. They lived down the street from my parents so that made it convenient I guess. This friend and I were never super close and as far as I know, no one ever found out. I broke it off when I was around 20 because the guilt finally caught up with me. About a year later he called me to tell me he was getting divorced because he found out his wife had cheated on him (couldn’t help but laugh at the irony there). He wanted me to be a shoulder he could cry on (and probably wanted us to pick up where we left off) but I shut it down pretty quickly. I’m almost 30 now and haven’t heard from him in years, but my parents still see him around town. Apparently he’s openly gay now, so in spite of everything that happened between us, it still makes me happy that after all these years he’s finally comfortable being himself.
But let’s not pretend every friendship feels like a warm hug. Some friends are the emotional equivalent of a speed bump made of Legos. They discourage your dreams, roll their eyes when you share your goals, and somehow always make your good news about themselves. They’re the ones who disappear when you need support and magically reappear when they need something from you. If you’ve ever felt worse after talking to a “friend,” chances are, they’re not really one. And sometimes, the hardest part of adulting is realizing it’s time to walk away from the bad ones.
