To feel uncomfortable that my boyfriend’s best friend is a woman he used to sleep with?

[TicklishCoralScroller]

They’re close - talk regularly, meet up for drinks, share memes etc. He’s been upfront about the fact that they used to sleep together years ago but says they’ve moved past it and are “just friends.” I try not to be insecure but I can’t help feeling weird about it. If the roles were reversed, I think he’d be uncomfortable. AIBU to say it bothers me and ask him to dial things back?

Nope. Hard no. Absolutely not. Men & women are never 'friends' especially after they have shagged. Ofcourse you feel uncomfortable. I would.

Friendly? Yes. Friends? No. I have no male friends that I would meet up with one-to-one. Before I was married then I did, but not now. Gay male friends? Absolutely. And I did include a list of exceptions, so it’s more that I wouldn’t be friends with any straight men 15 years either side of my own age, which actually leaves quite a few.

But anyway, I don’t want to be reminded of Hector’s wrinkly ballsack when I have time off to socialise, so that’s why I never stayed friends with exes. Seems weird to me to stay friends with someone you’ve had sex with. Either you liked them, in which case why did you split, or you didn’t, in which case why shag in the first place? But it just goes to show how boring it would be if we were all the same.

I'm not sure this is a problem. But if it is for you then best end it. You won't win this battle.

I was the friend of an old boyfriend, we stayed friends and kept in touch although I wouldn't say we were best friends. He left me.

Neither he nor I ever had a sexual encounter again. I ensured anything we did together without his wife was OK with his wife, i.e. ask to speak to her to check. I had no desire to tread on her toes. I even occasionally stayed over and vice versa, again with it all in the open and wife in agreement.

However he told me one time he was struggling to keep his feelings in check. I was happy being friends but I don't help anyone to cheat and don't cheat myself. To be fair to him he didn't want to blow up his family either so we stopped being friends who did things together and never did anything without his DW again. He and DW did divorce after several more years, nothing to do with cheating

So it's all down to the individuals but even two people who didn't cheat doesn't mean that feelings weren't there. It's sometimes easier to explain away inappopriate feelings to yourself when it is someone you have already been intimate with.

What I'd say OP is if you are uncomfortable with his relationship, that's probably never going to change. Whether he and she ever do anything again is not the issue, it's how you feel about it. If you can't live with it I doubt you can do much about that.

Ahhh, how gratifying it must be to do the “pick me” dance - even more so when your rival is an anonymous stranger on the internet.

Mmm yeah I’m married to the guy who was my ‘best friend I used to sleep with’.

Exactly this. There must be better options out there op.

I can see why it makes you uncomfortable although having sex in the past can mean little in the present (I have a close friend I used to have sex with and I think both of us would be disgusted at the thought of having sex either each now - we’ve moved into a brother / sister style relationship.)

No harm in asking him to dial it back but what will you do if he does not?

Nope

This is probably my view but then I am in the situation of having a friend I used to have sex with and so understand it’s perfectly possible to move past that into friendship.

But if OP feels uncomfortable then she should raise it and he may agree to dial things back or accept OP is not the woman for him.

I find it baffling that you find it baffling that people can be friends even if they had sex in the past.

Some women just like keeping old lovers in their social 'rotation'. Hard rains are gonna fall etc... good for backup.

But usually only if the guy is still into them. Power is heady. Rarely if he was an arsehole or hurt her.

They did say they dated - they said they had sex. So no “splitting” involved.

I doubt VERY much whether he'll stop seeing her or even messaging her OP. If it makes you feel that uncomfortable, (which I really can understand), I think you'd do better to end the relationship, and look for someone who doesn't have a female best friend, as all too often it leads to major rows and insecurities, which is totally understandable in my opinion.

So what's changed recently if it didn't bother you for a year, or have you only just found out?

Nope. Friends are everywhere in life. Theres no value in staying close friends with someone you used to shag on the regular.

Tell him to find other friends that are not his ex. That’s fair enough in a relationship.

Why would they stay friends with an arsehole?

I'm friends with some of my exes. I'd rather have a new boyfriend than lose their friendship. I don't want a boyfriend who thinks I would lie and cheat behind their back anyway.

I would think if they wanted to be each other they would, so I don't think it would bother me that much if I felt secure in the relationship

I stayed friends with an ex. He decided he felt like we were more friends. I was a bit upset initially, mainly because I was carrying baggage from a previous nasty breakup. But we did get on really well and had a similar sense of humour. We also did the same sport. Plus I was moving back to his area, didn’t know people, and was meeting friends through him. So we still met up and I went out to the pub with him. His following girlfriends weren’t overly impressed with me, despite my being friendly towards them. I never ever felt the desire to get back with him. He once asked me and I said no, he’d been right, we were better as friends. He was a bloody nightmare with women, he always had a few on the go behind his girlfriend ’s backs. Seriously I was the least of their worries! Eventually we both met long term partners who could cope with our friendship. We both went to each other’s weddings. Twenty years on I don’t see as much of him as I used to. My husband probably sees him more than me.

I have been in this situation and I think it only really works if there's an openess in their friendship. This isn't just a female friend it's a close friend and he's slept with her. If he involves you in aspects of the friendship that's one thing but if you feel the third wheel then absolutely not. Just be careful this isn't triangulation. Some men just feel validated by female attention even if there's nothing going and it's a form of gaslighting.

I don't think there is a comprehensive answer really. Your boundaries are very personal to you and just because someone else feels differently it doesn't mean how you feel is wrong.

I wouldn't like this situation, but also wouldn't feel fair telling him who he can be friends with. It's tough. I'd probably end it.

I totally get how you feel but I have a male bf and we have known each other since we were 12. Once in our teens and briefly in our 20s we slept together. It never worked for us to have a relationship but we love each other as friends. All these years on there is no world in which we would ever be intimate again but we are best friends. DH totally understands and there’s no issue at all. Bf has had partners that understood and those who didn’t but the ones who didn’t never lasted. You’ve been together a year but I’m guessing the friendship is much older. If you want your relationship to last you can’t tell him who he can be friends with and you need trust. If you can’t trust him then it’s not going to last anyway. So I’d really think about this long and hard before telling him it’s her or you. You might not like the answer.

I’m not a jealous type and I have good self worth but I just wouldn’t feel comfortable with this. If they found each other attractive enough to shag and are now friends and enjoy each others company then I would bow out of this for my own sanity.