Didn't tell friend that I have slept with new man

[Freinddilemma]

So 3 years ago, I had a random 4 months where I was sleeping with a male friend of mine, lets call him Tom. Nothing serious, we had been friends for years and years, and then we just randomly hooked up one night and had like a 4 month "fling". It ended as suddenly as it started and we went straight back to being just friends with zero flirtation or anything.

Anyway, I have a very close female friend, let's call her Emma. She is absolutely bloody lovely and was dumped by a total prick she was seeing. It suddenly occured to me that there was a very similar kind of feel that Tom and Emma share, and that they would really get on. So I introduced them.

I dont know what the fuck i was thinking but I somehow never got around to telling Emma about how I had this thing with Tom. She knew we hung out and were frjebds and stuff of course, but back in the day i never mentioned we had slept together as it was so casual, and i didnt mention it before hooking them up either. I guess because I wanted her to feel like if they did hit it off, he would be just hers to know if you see what i mean. I don't know, initially I just wanted her to feel like she was meeting a great man and it felt somehow sordid. Like "heres a guy I used to shag, why dont you have a go".

Rightly or wrongly I failed to twll her, it has been 6 months they have been dating and I feel like its now past the point of no return as she is massively falling for him and I have missed the boat on telling her. He hasn't told her, I'm sure of that - she would have said somrthing to me.

Have I massively fucked up here?

I wonder why he didn't tell her, you'd think it might have come up quite early on from him if nothing else, given the context.

I think I'd still push to tell her just so she knows, even if the conversation might be a little awkward I'd probably explain that it was such a non-event that initially it didn't seem necessary and you didn't want to make more of it than it actually was when you were so excited to set them up.

You're all adults, I think in the context that you very casually were seeing him for a short time, it came to nothing and then you went out of your way to introduce them, I really can't see how a person would be annoyed by that part of it, we aren't obliged to every detail of a new partners life from the off and it sounds fairly new. It's not as though you knew anything would actually have come from introducing two people either.

I'd pull the plaster off and get it done but I'm sure there'll be people come along to say they'd leave it. I think I'd just not want him to find out from her, and would assume it will come out at some point as these things inevitably do.

I wouldn't tell her.

Unless you're still shagging him I can see why there would be any reason to share this info with her. Keep schtum.

Why on earth would he ever want to bring that up?!

"Oh by the way, I used to shag your best friend"!

It's weird that you would introduce your friend to a guy you used to sleep with in the first place, and yes you should have been transparent and mentioned it earlier so she can decide if she wants to go ahead or not but now it would be very weird to bring it up when she's 6 months into the relationship with the guy.

At this point I would just keep quiet because bringing it up would just be dropping a bomb in their relationship. Having said that if she ends up finding out later especially if it's from someone else the feelings of betrayal would be a lot worse eg finding out after they are married or have kids etc and you've been playing the perfect supportive friends for years.

I don't think there's an easy answer now because the opportunity for a straightforward conversation has probably passed.

If I had a friend who introduced me to a great guy at a low point in my life, waited months for me to bond with him before then revealing she slept with him, I'd view her with great suspicion. It would feel like she wanted to take something away from me when I was feeling better about myself or she became so jealous of how well it was going that she had to throw a spanner in the works despite their past not being a big deal to her at the start.

You'd be the ultimate red flag and I'd tell all our mutual friends how shady you are.

Thanks for your replies. I agree I have messed up the timing here and its difficult to come back on. And i dont even want to ask Tom about it as then its like creating drama.
It was so stupid not to mention it but I thought i was doing the right thing at the time.

The important thing to remember is that no one's done anything wrong. You had a brief fling with a male friend years ago and now you're 100% platonic again - totally normal. You haven't betrayed her and neither has he. There isn't really a good or natural time to tell her the information so you shouldn't beat yourself up on that front.

Ultimately you can't control anyone's reactions. I think in her position, the normal reaction would be to feel a bit weird momentarily, but then to get over it because it isn't actually a big deal. If she reacts badly, it's about her, not you.

If he hasn't told her by now, I would just keep quiet too.

I wouldn’t tell her. I would say you thought she knew already if she finds out. Making a point of telling her makes it more of a big deal than it needs to be.

That's a good idea. I could tell her I thought id told her way back when. Which is dishonest but the kindest solution

If I were Emma, I’d be grateful you’d thought to introduce me to someone I hit it off with, such a lovely thing to do.

If I found out from a third-party that you and Tom had a history, I’d understand why neither of you had mentioned it, but I think making a point of “there’s something I should tell you” now might be a bit odd. So my vote is not saying anything.

I don’t see the point. Your relationship with him was completely different, you are still friends and it happened to be a bit more than that briefly for the pair of you. You introduced them to each other in a completely different manner because you like them both and feel they’d be a good match. At least you know what he is like and you should feel pleased that two people you have such friendship for like each other too. You’re entitled to a private life and from your post you sound genuine, not someone who still fancies him or wishes there’d been more and is resentful of her friend and wishes to upset the apple cart and cause drama.

No need to ever say anything.

if it does come up then “oh, it was nothing, thought I’d told you at the time” but certainly don’t go out of your way to mention it now. That just seems like making drama for no reason.

Thank you, ive decided im never going to mention it to either of them and if she does find out one day I will tell a white lie and say I thought id told her about it when it was going on back in the day

I agree with PP about mentioning it now specifically might look like causing unnecessary drama. See how their relationship pans out. It may be the sort of thing that comes up over dinner and drinks in ten years' time, when you're all settled and secure in your own relationships.

don't ever pretend you told her and she's forgotten - someone wouldn't forget something like that and implying it would mean you are more than happy to put your need to settle your own feelings of discomfort over her feelings.

just leave it now and if it comes up be prepared with what you are going to say. In reality its only likely to come up if he tells her in anger one day.

Old saying - It is aint broke dont fix it...

Why rock her boat?

You don't have to tell your friends who you've slept with.

Yeah I wouldn't say "I thought I'd told you" because that's a lie and she'll probably realise that. And being dishonest will make her think you're hiding things.

Say nothing for now and if she finds out just tell the truth. You didn't tell her because there wasn't a natural time to do so and it wasn't a big deal because it was so brief and so long ago. That's all you need.

You didn't do anything wrong at all. It's not as if you are still harbouring feelings for Tom. I would just say nothing at all. It's not relevant to anything.

Don't say anything until you get to the Matron of Honour speech then drop it...😀

regardless of should have, would have, you didn't. just block it and move on.

are you a little bit jealous you got a 4 month fling and she might be getting true love?

I'd tell her if she was a close friend I really cared about. A casual friend I rarely saw, I wouldn't bother. These kinds of things always come out eventually. If they're together years he'll probably tell her and she won't view you kindly.

This is so needlessly catty.