I'd vote for "keep my damn mouth shut". Revealing what you know could lose you two friends.

"Y. told me this a long time ago in confidence, and it's definitely cool, but I didn't want to keep it secret from you that I know"

This sentence, to me, says that you would violate a confidence. (I don't know if that's true of you or not, but that's the way it might sound.) Probably not the way you'd want to start things off. If it were me, I'd just sit on it until the subject came up of its own accord.

In my recovery fellowship it's usual practice for people to find themselves a sponsor - someone to mentor and guide them. Anything said to a sponsor is meant to be in strictest confidence but I know one person in particular who can't keep her damn mouth shut and I've had to stop being in one-to-one situations with her because she tells me private things her sponsees have told her justifying it with "I know you won't tell anyone".

It's made me uncomfortable, because I hate, absolutely HATE, being in someone's presence and thinking "I know something about you, something secret, and it wasn't you who told me".

But equally, I know I can't say anything to the person, because I think it could do more harm than good.

What I'm saying is: two wrongs don't make a right. If you've been told a secret, keep it a secret.

Don't tell! There are so many ways it could work out badly, and only one way it could work out well... and the one good way it could work out will probably work itself out naturally.

Also, consider: what Y said about X may not even be true. People are weird; sometimes they lie for a reason, sometimes they lie for no reason at all, and sometimes they are so casual about things that seem very important to you, that they just make mistakes while flapping their lips. "Oh, did I say that happened with Y? No, heh-heh, that actually happened with Z."

Hmm. Okay, okay, this is helpful. Well, it wasn't explicitly said in confidence. I don't believe he has told anyone except maybe the last woman he was in a relationship with. But he never swore me to secrecy. In fact on a couple of occasions we've talked about the three of us getting together... (This probably gives away what I'm referring to.)

This definitely gives me pause for thought. I want to make it very clear that the impetus for telling him would be so that I don't have a secret, not to be a gossip or to make him feel bad. I'm actually trying to prevent making him feel bad later! I'm trying to imagine the situation in reverse, and I don't think I'd be too freaked out to find out down the road that a guy I'm with already knew about something very personal I'd done. But then, there are societal pressures on men that aren't exactly the same for women. I just don't want X. to feel betrayed or uncomfortable that I held this information while I was romantically interested in him. Wouldn't that seem creepy? I'm pretty sure at some point when he decides to talk about it with me I will have to admit I knew. I can't lie forever!

I do think Y.'s telling the truth, and it definitely wasn't an offhand remark; we've discussed it a few times . But I definitely get something from that notion of truth/lies. I wouldn't want to act like I know all about something when I might not have it right (as I've mentioned, I've, errr, ruminated on it somewhat extensively) and anyway, it's none of my business because I didn't know either of them at the time.

(As a side note, if I want to pursue a relationship with X. then I wouldn't pursue the party-time-excellent scenario with both X. and Y. Unless X. wanted to and/or suggested it. Maybe.)

I don't think I will say anything. Not for a long time if at all. You can see why it's a tough situation, though, right?

Oh - and I should say, I don't believe either of these men are hung up about it. They're not volunteering the information but I know for sure at least Y. isn't ashamed or weird about it.

If it were me, I'd just sit on it until the subject came up of its own accord.

Yeah. I think maybe that will be the best thing.

I just don't want X. to feel betrayed or uncomfortable that I held this information while I was romantically interested in him. Wouldn't that seem creepy?

See, I think the opposite. I think it would be creepy to come forth with your info. Keeping it to yourself is not creepy. You're SO overthinking this. Plate of beansing it. First of all, there may never be a relationship, so even fretting about this at this point is just not productive. Secondly, if it ever comes up and he tells you what happened, just say something like, "Oh yeah! I'd already heard about that a long time ago from Y - no big deal". Or..."Yes, I knew. Why didn't I mention it to you? Um...because I didn't think it was a big deal."

Because it isn't, right?

"... I don't think I will say anything. Not for a long time if at all. ..."

Danger! Danger! Danger, Will Robinson! Danger! You are mentally prepped to blurt out this "secret," probably at the worst possible time. Keeping confidences, even loosely presumed ones, is a major mark of emotional maturity. And for a lot of people, including me, it's a key element of any personal relationship that isn't completely arms length.

If I found out you couldn't keep other people's confidences, especially about something they'd told you about me, flattering or not, I'd have to presume you couldn't keep confidential anything I told you either. So, I wouldn't tell you anything I wouldn't mention to the grocery store clerk while shopping. I'd expect in fact, as you met my friends, and formed your own relationships with them, that they would tell you things about me, in confidence, that would offer you insights into their relationships with me, and deepen yours with them. And I'd be squicked if you then repeated these to me, good or bad. And I'd be honor bound with most of them, to tell them that you couldn't be trusted with confidential information, either, but not how I'd come by that knowledge.

So keep what you think you know to yourself. Permanently. It's not that hard for adults.

What ico said. It sounds like something that will certainly come up if things go the way you want them to, at which point it will either not be a big deal at all, or, if he gets all, "I have something to tell you" about it, you get to be the cool chick who says, "Oh, yeah, I knew that, no big deal, actually it's kinda hot."

I would suspect that the conversation happening at any other point, especially before the romantic relationship even exists, would be weird and awkward.

I was scrolling down here to say what iconomy said. By not mentioning it until it comes up, you can make you point that it's no big deal and you get to keep the confidence as well. Everyone wins. Just because someone doesn't swear you to secrecy doesn't mean they expect you to blab either - it would be implied that they told you something private because they assume you will keep it to yourself.