Do I tell him?

This is a repost blog.

Original posts by miss-sage-sativa on subreddit r/dating on Reddit

13 Jun 2023: Do I (26F) tell him (26M) that I have sexual history with his friends?

I (26F) have a second date tonight with a guy (26M). Our first date was last week, we went for drinks and then he walked me home and hugged me goodbye. For our second date I’m going to his to watch a movie, so one can imagine that more intimate activities may occur.

The thing is, we’ve known each other since we were in our final year of high school. Long story short, some of my friends were friends with some of his friends so despite going to different high schools, we all did occasionally party together. Within that friend group, I hooked up with one guy (just making out and hand stuff, as you do) and actually lost my virginity to one of the other guys. This was all in our final year of high school. Both were one-time things and there was no emotional attachment or anything like that. I lost contact with all of them when we went off to different universities.

Fast forward to a couple weeks ago, we match on a dating app. We both remember each other and decide to reconnect over a date. I wasn’t too worried about it, as all of that was almost 10 years ago but he mentioned that he’s still really good friends with both of these guys and sees them weekly. 50% of me assumes he already knows, as no one was trying to hide anything back then, but you know what happens when you assume…

Just curious if I should disclose this to him before we’re intimate? Don’t want to ruin the moment by being like hey, I banged your friend!” but also would hate to be intimate and he somehow find out later and then feel like I was withholding information from him…

So what should I do?

14 June 2023: Update

Firstly, thank you for all of your thoughtful responses, advice and kind words. It was really helpful 🩷 Apologies for the delay on my update, had to wait 24 hours to be able to post again.

Now, onto my update…

I told him!

Once we were over the small talk and catching up, but far before anything spicy was going to happen, I brought it up.

Me: Hey, don’t want to make things weird, but you know I’ve hooked up with two of your friends, right?

Him: …what are you talking about?

Me: Oh, you know names

Him: …

long pause

Him: bursts out laughing Of course I know, what else do you think teenage boys talk about?

Me: Okay good, so it’s not weird for you?

Him: Who do you think I was out golfing with when I liked you on Hinge and got their blessing right there on the spot to pursue you? We had a good laugh but don’t worry, that was almost a decade ago.

And there you have it folks, all went well and he did know, as many of you predicted! He also is not bothered by it at all, and we even cracked some jokes about how fun it’s going to be hanging out as a group.

We had a great second date and already have our next one planned!


Remember, this is a repost blog! If you comment here, the original poster is not going to see it.

October 24, 2023