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

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.

Nope

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?

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

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

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.

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.

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

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.

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

Agree, quite pathetic. Never mind OP’s boyfriend, where is hers?

I think it depends when it was...in my uni friendship group a lot of us have done things with each other, 25 years ago! I'm pretty sure it doesn't affect any of the marriages (some are married to other people from uni who also did things with other people we know!)

Late teens/early twenties I think should be written off, more recent, serious liaisons might be worth a consider, but ultimately you either trust your partner or you don't

I’ve slept with a few people who I am still friends with (my DP knows). I don’t see the big deal myself- if we were going to be anything more it would have happened in the many years of opportunity we had before I met my DP.

However it’s an issue for you, so maybe you and he aren’t compatible.

Because often shagging someone entails liking their company and character, not just their face and body? And if you realise you're too incompatible (sexually, domestically, politically, lifestyle-wise) to be a couple, you don't stop enjoying their company? Staying friends with someone you had a brief, meaningless fling with is so commonplace to me.

Those exes are the least to fear for new partners. If there was a viable relationship there, it had all the opportunity to happen, and there's a reason it didn't.

(Also, thinking that men and women can't be friends is batshit even beyond that.)

Was your last sentence really necessary? Horrible comment.

I find this so baffling. Why would I stop being friends with someone just because I've had sex with them? And how can you rule out any form of friendship with 50% of humans?

But I do think this is a fundamental compatibility thing. Neither of OP or her boyfriend are right or wrong, but I think it is something you have to see the same way.

Friends - is in a shared sense of goodwill, pleased to have a catch up when with mutual friends, perhaps checking with each from time to time to share good news etc - fine. Healthy.

Best friends - absolutely fucking no way.

I could well be the other woman here.

I'm still friends with him but have absolutely no Interest in sleeping with him. He was fun back then but was and is immature, too much angst and drama.

I have been in his life for 10 years, supported him through the loss of his dad and his cancer scare. Don't be surprised if he chooses me over you.

This is a no from me. He will never give up the friendship and you will never feel secure in it, quite understandably. But I’m someone who doesn’t think men and women can be friends unless: the sexual orientation is opposed (eg lesbian and a heterosexual man); they have known each other since they were babies; they have a huge age difference.

Why would anyone be friends with someone they shagged, unless 20 years ago? “Darling? This is Jane who I saw orgasm repeatedly last year! And she knows my sex face too! Such fun!”

I dunno. I’m happily married and have been for years and years - 2 young DC, the lot.

Pre-DH I used to regularly have sex with my best friend. Sober, drunk.. you name it. Best sex of my life, he was the most attractive man I’d ever seen. We were all over each other.

Then we weren’t and it took a little bit of adjusting to, but now? Like a decade later? Nothing more than friends. I see him a few times a month, we speak every day. We are friends. We spend time together alone, we drink together regularly. My DH couldn’t care less, he likes him. My best friend even minds our cats for us when we go on holiday, and physically helped us move house (12 hours and the customary beer and pizza after.)

I really couldn’t care who has had sex with who, it just doesn’t infiltrate my thoughts. DH was no virgin when I met him, but hey.. he married me.

I can completely understand why this would make you feel uncomfortable. There’s nothing you can do about though so either end the relationship or accept it. If you stay with him the obvious thing to do is befriend her yourself.

I can see why you’d be uncomfortable but the friendship existed before your relationship so you don’t really stand a chance of winning this.

Assuming he was up front about her from the beginning, you have chosen to continue the relationship. If it doesn’t work for you and that’s absolutely ok then you should end it.

No. This wouldn’t work for me at all.

However, I don’t feel comfortable with telling him who he can be friends with. I think you are incompatible.

No, that wouldn’t work for me

Before you start doing ultimatums or thinking about leaving or asking him to dial back contact etc, why don't you start by getting to know her? I think that if you spend some time with her - especially if you do it without your partner there - you'll fairly soon work out if there is something there or not.