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?

I think that's over simplistic to say they're 'the least to fear' because the relationship wasn't 'viable'. It assumes that they mutually agreed they were better being just friends. In reality that's pretty rare. Generally couples spilt either because they no longer want to be around each other (so no desire for friendship) or because one doesn't want the relationship. Its very common for this to result in a 'friendship' which for one is settling for something as better than nothing, while still wanting more and holding out hope, and the other enjoying the ego boost and security of a person they've rejected for a relationship still being there for them. Unfortunately the OP doesn't know which is the case and her bf is hardly likely to tell her if he was left heart broken, and is being Johnny on the spot in case the woman ever changes her mind. These situations cause a lot of uncertainty, and there's no reason why the OP should stay in a relationship with something like this chipping away if she doesn't want to. Most men do not have a best friend they used to sleep with, so she has alternatives. He on the other hand is unlikely to have a queue of women delighted by his situation.

It's fine for you to leave the relationship because you are not comfortable with his friend, but it's not fine to tell him who he can be friends with. As you can see on this thread, plenty of women would be OK with their boyfriend being friends with someone they have slept with in the past so he has every chance of meeting someone like that instead and then he can keep his friendship. It's a compatibility issue and it's a substantial one.

This is a you problem OP, don't be insecure and jealous. Unless you suspect / evidence they are sleeping together. Then dump his ass.

You can't control who he's friends with but you would not be in the wrong to leave him because of this. If he's leaving you to go and spend time with a woman he's previously fancied and been intimate with, that's a problem. I think the only situation that it might be ok is if they were long term friends, slept together once as a mistake, then went back to being friends with nothing sexual happening since. It's not really about if you trust him or not, it's him potentially putting you second to another woman when you're his partner.

It’s not always something to worry about.

One of my best friends is a man who I dated in on and off fashion from mid teens-early 20’s. More off than on.

We message regularly but now, both being married with families and jobs, free time is scarce, so we tend to meet with our spouses as a four. We all get along really well.

We’ve been good friends to each other over the years since our youthful on/off phase, it’s ancient history. He has never been so happy as he is with wife, I’m the same with my husband.

Nope. Wouldn't be cool with that. I'd be off.

Meanwhile, back in the real world,nobody would be cool with that set up.

I don’t think there’s a right or wrong with this. It’s very character dependent. However, if you’re uncomfortable with it it’s ok to feel and say that. He then has the choice to decide what is more important to him.

Some people are. I am one of those who have had no issues with boyfriends being friends with exes. I also have a close male friend that I used to date. There is nothing sexual between us anymore so I know it's definitely possible.

Two of my best and closest friends were ex-boyfriends. We were friends for decades after we split and the friendship only ended on their deaths.

If a newish partner had expressed unease at these close friendships, it would have rung massive alarm bells. If they had asked me to "dial things back" with regard to those friendships, I'd have been very resistant to it.

If they'd continued to express disquiet, I'd have told them to grow up or fuck off.

Neither of their partners were bothered by our friendship either.

Well yes, the specific scenario you describe isn't a healthy one for anyone involved. I disagree that it's the norm though. In my experience if one person is unhappy about the split they tend to keep far away from the one who dumped them. Obviously in mutually acrimonious splits there's usually no contact. But contrary to popular myth, most splits I've witnessed have either been mutual recognition of incompatibility or a mundane fizzling out. In those cases there's no rational reason to Fear The Ex.

Plus people's partners don't tend to exist in a vacuum. They don't vanish into the ether once the relationship ends - in the cases where neither party wants to see the other again, they have to actively make an effort for that. Most people find partners from wider social circles, political or artistic scenes, professional industries and so on. Which means that after the relationship ends you still have mutual friends, interests in common and social events where you're probably going to see each other again. It's not really the norm for exes to default to NC.

I'd also ask yourself why you are raising this now after you've been together for a year.

I would NOT be okay with this. At all. But it’s unreasonable to expect him to choose, so I would’ve thrown this one back a lot earlier than one year in.

Do the three of you hang out together? If never, I can see why it bothers you.

Depends on how long ago it was, and whether I was at least somewhat included.

If years and years ago since they last slept together and it was very upfront (i.e. he wanted me to get to know her and vice versa and it went well) I couldn't get het up about it. Lots of people end up really close platonically with an ex. Though if it was FWB I would be more cautious as clearly they're sexually into one another and I'd be curious why it never turned into a relationship.

They weren’t a couple - why do you keep referring to them as being a couple?

I would not care. And to my knowledge I live in the real world. Unless they were behaving strangely or trying to hide their friendship away from me.

But then I have a friendship like this.

A man staying friends with a woman makes him “not a decent man”?

Whut? He is not doing anything to his partner. She does not like the friendship which is her right and may mean they have to part ways.

There's a difference between telling someone who they're allowed to be friends with and communicating with your partner that you feel uneasy about something.
If my partner was messaging someone everyday and regularly meeting up just the two of them, combined with the fact they used to sleep together I would let him know that situation was too close to a romantic relationship/dating and that it was worrying me. It would then be up to him what to do about it. That's not controlling it's called communication. I was cheated on in a situation like this, not physically but through innapropriate messages where they just took it too far and basically admitted they fancied each other. It was extremely hurtful.
I think it's great for men and women to be friends in a wider group and for couples with children to all get together and that's what my life looks like now with dh, but if it looks and feels like an emotional affair then it probably is one. He should be taking YOU out on a Saturday night not meeting another woman for drinks just the two of them.

I actually do have a few male friends like this, and it’s genuinely friendship. However, I did cut them out because it made my husband uncomfortable when we started dating and yeah, fair enough

What I don't understand is why anyone would want a partner who only isn't cheating on you because you control who they spend time with.

Wouldn't you prefer a partner you can allow out of your sight without worrying they're heading dick first into someone else?

As I said – staying friendly: fine. Being every day besties, texting daily and meeting up for drinks/lunch/dinner frequently, being described as 'close': wholly unnecessary, and completely understandable in how it would make your partner feel uncomfortable.

OP can't dictate what he does, but she can explain how she feels and her boundaries – what happens next is his choice entirely.

I don't. I was responding to a general point about people staying friends with exes and why it is not necessarily 'safe' because if they had wanted a relationship they'd have had one. The point being is takes two to want a relationship and its entirely possible OPs bf did and does, and the woman didn't so he's hanging on in hope. Of course, it's entirely possible not. The only certainty is the OP doesn't know either way, so in her shoes I'd not be chancing it, given most men do not have women they used to sleep with as their 'best friend'.

I'd be uncomfortable!
Trouble is I'm the wrong person to comment as I firmly believe "best friends" have to be of the same sex (for straight people).

This!! Why can you no longer be friends with someone just because you had sex in the past