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?

He might have told her
and it’s no big deal for her so not mentioned

Is anyone else likely to tell her?

If not, I wouldn’t.

No. Sorry to dedramatise what could have been a nice mid-morning hate-reading session for you

Tough one @Freinddilemma both you and Tom might have thought it was the other person’s ‘secret’ to tell and then both left it and now it is almost too late. He won’t tell her because it would put you in an awkward position and you don’t because - it’s been so long it would be more unsettling for your friend. Yes, in hindsight, you should have told her, but, you can’t turn back the clock. I don’t know what to suggest - it might help to write down ‘what you would say if you were to explain why you didn’t say/why you left it’ but I still think keeping quiet might be the right thing now it has been so long … “arrgh” completely get how you feel though!

Why are you not thinking he’s told her
and because it’s of little interest to her - she’s not mentioned

I’d be the same in her shoes

Because they all know each other and she was the one to set them up so it's hardly outside of the realm of belief that he might at some point mention that they used to date? Not sure it requires it to be posed as dramatically as possible for effect, rather than just casually mentioned so that she knows and doesn't feel foolish when she eventually finds out.

It's not like it actually meant anything so why would it need to be proactively kept a secret by all parties. As I mentioned, people will view it differently and presumably would deal with it differently in real life as a result. If I started dating someone in that context I'd have mentioned it. Anyone with an ounce of maturity would just understand it for what it was and move on.

Perhaps he has already told her and because she knows it was not serious and meant nothing long term to him… she’s not bothered enough to mention it to you

No I dont tnink she needs to know ... why would she now.
If you had spoken as friends about it in the past then fine that way but I dont see the point in either of you bringing it up unless you want to chance spoiling your friendships they might not feel as easy going you will cause unease .

Not if both friends see it as nothing and it was a short fling.. why tell her something that just doesn't matter anymore silly advice.

Completely being nosy here just out of pure interest, How did you end up suddenly not sleeping with him? Did something actually happen? Did you have a conversation? Or did you just suddenly stop having sex?

Exactly fkn shit advice or what.

No there was no conversation. It was quite baffling really. We had been friends for 12 years with absolutely zero flirting. Then there was this one summer where we were both single at the same time and I cant even remember how it started but we just slept together. Then a few months later he met someone new and we both went straight back into friend mode like nothing ever happened. When we were having sex there wasnt anything romantic or sensual about it. It was quite kinky sex actually 😂

It sounds like they are serious about one another.
He will likely have mentioned it to her over some drinks, they’d had a chuckle about it, and then moved on. Because it didn’t mean anything to him, your friend isn’t bothered and so hasn’t mentioned it to you.

So I’d just leave it

Agree with others, it won't sound great if you bring it up now, at a point where the two of them are doing so well together. You sound absolutely lovely, but it might give the impression you're a bit jealous and want to cause trouble (I know that's not the case)
To me, it's actually better that you hadn't said anything if she did ever find out, as it suggests you didn't think it was that important! If she does find out I wouldn't lie, I'd just explain it as you have done here. I think if you make out you thought you'd told her she will know that's not true

I’m with the don’t mention it camp. I don’t even think it needs to be an insidious / sordid “don’t tell her”, it’s more that it just doesn’t need to come up because it’s not something you think about enough for it even to have been a blocker or consideration. Unless you’re actively trying to sabotage a fledgling relationship after proactively matchmaking the pair - I have no idea why this information is even relevant. Two distinctly different timelines and seasons in life with no crossover - it’s not like you were shagging while they were having first dates. It’s up to him to disclose his prior sexual partners and if you really don’t care about him ‘in that way’ anymore, it doesn’t really serve any purpose to offer the information. If she ‘found out’ (aka he disclosed a piece of his history as a plain truth) then I simply don’t see the disclosure drama. Maybe if he was all “I’m in love with her after all this time” malarkey, but then that would be a blindside even to you. If she ever learns of this information, and questions it, just treat it as a very plain boring fact and don’t give it energy that grows it into something sordid. “Ahh yes, Tom and I had a brief fling, but to be honest it’s never even been something I considered a big deal - we were much younger. I am personally very pleased to see you two together as I think you’re a fab match and both deserve happiness together”. Conversation done. Let’s look at the other narrative here too shall we - imagine if you HAD told her and it stopped her pursuing the relationship because she was then a bit doubtful of the past you pair had? Instead she’s not had that clouding her judgement and the pair of them are cracking on, which was your original intent in the first place. If it needs that spelling out to her later down the track then you can assert this point to, but I personally just don’t see this coming up. Other posters getting all “tell her” are framing this as though you’ve been harbouring some huge dishonesty when really it is just a private matter in the past. If someone told me to date a person but they’d slept together it would actually feel like a weird claim being made from the start so I personally think you’ve done the right thing not mentioning it.

This

I think it’s extremely unlikely that he would tell her. What would be the point? No real positives in telling her, but a reasonable risk that it would make things weird between the three of them, messing up the friendships, and potentially even ruining the relationship if it makes her suspicious or jealous.

Don’t underestimate how much someone can overthink or distort being told something like this. And it’s really naive to think that she would automatically take him telling her “it’s not like it actually meant anything” at face value. Don’t you realise how many women’s minds work?

How many women would just laugh off her boyfriend telling her “btw, I used to have kinky sex with your best friend - it wasn’t serious but we carried on for a few months”… Seriously?

Exactly. Actually the thing im dreading is if she ever tells me anything about their sex life, which is unlikely since its been 6 months now and shes very private.
But if she did, I would have to blatantly lie to her at that point.
Im not going to say anything. But it does feel very dishonest and uncomfortable. I guess thats my problem to deal with, lesson learned.

I wouldn’t tell her absolutely no good could come out of it. I wonder if Tom is wondering the same thing about whether you told her or not .

I wouldn't tell her.

This. It looks like you’re jealous and trying to break them up to tell them now, just let them be.

why would he say kinky sex?

and not just a casual meaningless FWB situation for a few weeks

he has either told her and explained it meant nothing and last a few weeks

or

it was so meaningless that it’s not even
occurred to him to mention and no point you doing so

How old are you op?