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The original was posted on /r/relationships by /u/GainingPeace_1111 on 2024-01-24 13:16:57+00:00.

My boyfriend has a long time female friend whom I’ve met. He has expressed she has been an important part of his past. This has included them being sexual a few times as well as both wanting to date but at different times -it never worked out due to some big issues between them. Not my favorite dynamic but I also believe men and women can truly be just friends as I have a handful of male friends (although none have ever been sexual). When I met her there were a few points that showed me she didn’t respect our relationship and a few that were just woman’s intuition. However, I trust him even if I don’t her so I’ve delt with my own insecurities here from my own past as he’s different than my past and I felt comfortable and encouraged the friendship because it’s important to my partner. I’m mostly secure in relationships and uber secure with myself.

I trust that he is in love with me and wouldn’t cross that line, however he shared with me recently that on multiple occasions she has expressed/tried to get him to be with her and he stated that he was in love with me. During this conversation it also came out that the majority of their conversations revolve around a sexual nature and “jokes”.

It took a couple days for me to process my feelings but when I did I expressed how this made me feel devalued, sad, and disrespected. I also expressed that while I can’t make him stop the sexual conversations that him being clear with her that he’s not interested(as he’s said to me) and him stopping the sexual conversations would make me feel more secure, valued, respected and that he respects the relationship.

He initially agreed and said he wouldn’t do anything to jeopardize our relationship. Then after a bit more conversation it was clear that he really “didn’t get it” and asked me if I just wanted him to cut all contract off with her. I said no I didn’t because they have been friends for many years and they should have a plethora of other things besides sexual conversations they can discuss. He then brought up how the sexual nature is “just her” and that she’s “having a hard time right now” and “free speech is so important” and that “he likes to talk about sex with a friend”. I didn’t really respond to these statements just listened.

It’s only the sexual nature conversation I’m uncomfortable with at this point because it’s VERY clear she doesn’t respect our relationship.

My question comes here: I’ve set my standard and what I need to feel secure, loved, valued and respected in terms of this dynamic. Yes, he could lie but I will NOT snoop and only want to practice honest communication. So How do I “check in” to know if this is being respected? How long do I wait after this initial conversation to “check in”? Because this isn’t a boundary that will be clearly seen in the course of our relationship and it is a 100% deal breaker for me. I will not move forward with a man that is willing to spend time and energy on sexual conversations with someone who doesn’t respect our relationship but I will not “force” anyone to be anything other than what they want to be/do. So I need to know/follow up so I can make my determination.

TL/DR: When is it appropriate to follow up on a boundary request that was set?