About our relationship:

My boyfriend and I have been together happily for two years now. We both love each other very much and we're always growing closer. We're planning to move in together in a few months, but for these whole two years we've always had one underlying issue.

The problem:

My boyfriend has always had close female friends. It seems no matter where he goes or what he does he's always befriending more girls. I know that he would never do anything to hurt me on purpose, but I can't help but be afraid that he'll unknowingly cross some emotional line and become too close to them.

I've tried to bring this up with him, but he always acts defensive and the conversation ends up going nowhere. He'll use arguments scarily similar to the ones being made in this question (though not nearly to that extent).

The question:

How can I successfully let him know how I feel so we can have a productive conversation about boundaries without him immediately getting defensive?

My ideal goal from a conversation like this would be to compromise on boundaries between him and other girls. Again, when I've tried this in the past by being straightforward he gets defensive and asks me why I can't trust him to be smart about these things. From my perspective, it seems like he should have respect for me enough not to put himself in potentially compromising situations (like for example, being alone with a girl in her apartment or her room).

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    I sympathize with your situation, but there seems to be some discord in your question. As I read it, your concerns seem to be that he will become too emotionally close with a female friend, and also that he places himself in potentially compromising situations with female friends that are not strictly related to emotional closeness (I don't see that being in an apartment alone together is more risky than, say, talking on the phone a lot). And your goal seems split as well- you want to let him know how you feel, but also want him to change his behavior. Could you clarify what your main goal is? – Upper_Case Jul 13 at 14:07
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    Have you asked about or tried spending more time with these female friends yourself? The OP in the linked question seems to be opposed to doing this himself, but if your boyfriend is more reasonable, it might help to defuse your concerns, if you got to know these ladies on your own terms. – Steve-O Jul 13 at 14:09
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    You should include the arguments in your question so we don't have to follow the link to read them – XtremeBaumer Jul 13 at 14:09
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    @XtremeBaumer It’s not that he uses the same exact arguments, though he does in some cases. It’s more of just the feeling behind those arguments. – Pretzel_Master Jul 13 at 14:30
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    What does he say if you ask him why he has so many female friends? – dbeer Jul 13 at 16:42

11 Answers 11

I believe that you are approaching this conversation in the wrong way.

First off with how you are talking to us about it you are framing it as a confrontation. Which is exactly what you said you want to avoid. If you go into the conversation looking to confront your boyfriend then you are framing it as a hostile or argumentative meeting which basically requires him to be on the defensive. Think about what your actual goal for the conversation is. Is it to have a confrontation with your boyfriend, or do you want to not feel insecure about their female friends?

This segues well into my second point. You've already had conversations like this before. Your boyfriend already knows how you feel about their friends. If the goal was simply to let him know how you feel, you've already done that. It seems to me like the conversation is more about trying to get him to establish some boundaries with his friends. When talking to partners about my insecurities I've found it helpful to have a solid understanding of my goal for having the conversation before starting.

The easiest way to not make your partner defensive when starting a conversation like this one is to use I statements. These are statements of the form "I feel [feeling word], when you [description of situation]. I would like [desired course of action]". Such statements are beneficial for a couple of reasons. First off they require you to think about the situation critically while you're composing the statement, which helps you have a better understanding of your actual goals as you move forward with the conversation. More importantly they frame things in a way that is much less likely to put people on the defensive. The speaker is taking ownership for their feelings and is talking about, not demanding, a particular solution. This gives the recipient time to respond without needing to defend themself or their actions.

This being said I personally don't think that establishing boundaries is your actual goal. It seems to me that what you really want is to not feel insecure about your partner crossing emotional lines with their friends and hurting you. It might be beneficial to reframe the conversation to be about finding a way to feel secure, with boundaries as a potential solution, rather than having your only goal being creating boundaries. When I've talked to my partners about my insecurities regarding their other relationships I've found that this is helpful to me since sometimes all I need is for my partner to acknowledge and empathize with how I'm feeling.

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    Thanks for the answer! During the last two years I’ve tried to take a similar approach with the solution you’re suggesting about finding a way to be more secure and the boundaries as just an extra. It hasn’t worked out well and only resulted in more arguments so I feel like at this point I need to go to him with a solution in mind. – Pretzel_Master Jul 13 at 14:36
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    @Pretzel_Master A lot of my answer is predicated upon your boyfriend being receptive and willing to work with you on finding a solution that will work for the both of you. When you've had these conversations previously were you using I statements to talk about how you were feeling, or were you opening with statements like "What you do with your female friends makes me insecure."? – sphennings Jul 13 at 19:11
up vote 22 down vote
+250

Having been in the boyfriend's shoes, I recommend that you take the time to understand what your boyfriend gains from his female friends BEFORE you start telling him how you feel about the situation. sphennings's answer list good technique in general about how to express your feelings on the situation, but it's important to not make the whole thing about you. You're asking your boyfriend to change a fundamental behavior and change his interactions with people that possibly predate your relationship. This is a big change that warrant taking the time to understand his side of the story.

Personally, in general, I prefer female friends some times, because all of the constant one upping and ball busting behavior with guys my age gets on my nerves. Some times when I hang out with guys, it suddenly feel really competitive and like everyone is trying to assert their dominance. My wife feels the same way when she hangs out with some of her female friends.

Strategies that work for my wife and I in this situation:

  • Give your partner an opportunity to meet and hangout your new potential opposite sex friend. It will make your partner feel more at ease if they get a chance to interact with that person too. Be sure to listen to your partner when they express their concerns.
  • Make friends together.
  • Set clear boundaries for what is acceptable behavior. Are one-on-one drinks off limits for instance?
  • Make sure the rules are reciprocal and fair. Otherwise one partner feels like they're getting the raw end of the deal. If you're asking your boyfriend to change your interaction with his female friends, you should also change your interactions with your male friends if you haven't already.

Before I answer the question directly, I want to say that I'm sorry for what you're going through and how you might be feeling. I also want to say that this isn't likely to go well for you.

I know that he would never do anything to hurt me on purpose

So you don't think he'll deliberately get feelings for someone else...

"but I can't help but be afraid that he'll unknowingly cross some emotional line and become too close to them."

... you just think he'll accidentally get feelings for someone else. Well yeah- that's usually how it works. People don't usually fall in love with someone else purposefully; it just happens. You might as well tell him to shield his eyes when he goes to the coffee shop because he may become smitten at first sight with the barista- that happens for people all the time, though usually not for people in committed relationships. You could also reason that it'd be appropriate to ask him to refrain from small talk with pretty women because who knows what could come from it.

Now, you may argue that I'm exaggerating a bit, and you'd be correct. But the point I'm making is: Where do you draw the line? And wherever that line is, you can't ask him not to cross it- all you can do is make a decision about the relationship if he crosses it.

How can I successfully let him know how I feel so we can have a productive conversation about boundaries without him immediately getting defensive?

I'm sorry but you can't have this conversation successfully. You're not establishing boundaries between him and you. You're not establishing boundaries between your shared home and his parents dropping by unannounced. You're trying to establish boundaries between him and his relationships with other people. I'm not saying that you don't have a right to be hurt or concerned but what I'm saying is that you can't negotiate the boundaries that other people have between each other. However this conversation turns out, even if it seems like it went smoothly, you're likely to find that you're not going to convince him to change his personality and the way he conducts himself with his friends.

You either need to trust him completely which means trust that he'll refrain from going further if he notices a spark of romantic interest for one of his friends, or you need to decide if he's crossing a line that you're not willing to put up with. But these kinds of conversations rarely have productive results.

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    Are you saying it's impossible for partners to establish boundaries about how they interact with other people? How does that work with common default boundaries like not having sexual relations with anyone else? In open relationships a lot of time and effort is devoted to discussing the effects of how our actions with others will affect the people we are dating. Are you really trying to say that it's impossible for those conversations to include a discussion of boundaries? – sphennings Jul 13 at 21:03
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    @sphennings "Are you saying it's impossible..." No. – 8protons Jul 13 at 21:04
  • Just that that conversation about it can't happen successfully? – sphennings Jul 13 at 21:05
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    @sphennings What I am saying is what I wrote. "But these kinds of conversations rarely have productive results." You don't go two years into a relationship to get magically blindsided by how they interact with friends of the gender that they're sexually attracted to. So either he's randomly changing his behavior or something is changing within her to get upset about it. Regardless, I stick to my initial point that you can rarely get people to respond well to boundary setting with regards to their relationships with their own friends. Your own parents? Sure. His friends? Not likely. – 8protons Jul 13 at 21:09
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    Can you explain why you think that? For me I've always been willing to have conversations with my partners about our insecurities. Sometimes the conclusions of these conversations include establishing boundaries with our friends. If I'm willing to talk to my partners about setting boundaries with my family and lovers why wouldn't I do that with my friends? – sphennings Jul 13 at 21:13

I have a theory on the "I don't know it just happens." part of this issue, which your description seems to indicate he does seems to be attracting them and that it is genuinely platonic. Another guy on the thread does too. And that does, actually, happen. And actually, there's the interest thing (pottery guy) but if you have a circumstances like this where no matter what, it seems to keep happening, sometimes there's a more psychosocial reason.

There is often a limit to the way straight men are allowed to interact with each other emotionally due to toxic masculinity, an adherence to traditional gender roles that restrict the kinds of emotions allowable for males to express in social situations. It hasn't always been that way but that is how it is now. Get too soft, too emotional, too vulnerable, too close, and you could be considered "feminine" or "gay" - the ultimate transgressions against traditional masculinity. The incomparable Tony Porter founder and CEO of A Call To Men, an sexual violence education and prevention organization focuses on healthy manhood specifically dealing with countering negative outcomes in the current socialization of boys in terms of respect, emotionality, understanding and understanding of the culture, deconstructs how the threat of being "girly" is used as a weapon against young men and how it represses their ability to connect with each other in his talks very simply. They aren't safe with each other not because there's something wrong with boys. There's not. The lesson's they're taught though, "Boys don't cry" "Be a man" "Suck it up" lead to a shared culture of emotional containment even when friendships develop. For a large number of men, friendships will not provide a safe or comfortable place for vulnerability and openness because of messages they received from family, friends, peers, older adults around them, the media, and society at large. Many of men who find themselves in those circumstances tend to rely on their romantic partner for all their emotional support because that's where it's "allowed" to feel things and share etc.

Now, of course, thats not the case of every man! Plenty of men are able to be vulnerable and connect with their friends, to lean on them for support and create deep bonds that go beyond social activities. But. The socialization is still there - the pressure of manhood behavior expectations exist even in close relationships, even if a given friend unit give that expectation the bird and share their souls to each other on the regular. Toxic masculinity has an influence that can linger and for some, it's a fact of life. However, there are a different set of restrictions for women and so women aren't like that in their friendships. Their socialization is different. Friendships between women often foster emotionality tend to train women to foster that open communication and support style in their relationships more frequently. Why's that matter? Well, sometimes even men who are perfectly capable of being open, emotional, vulnerable and connected to themselves and other people 100% platonically, the socialization still left a mark on this aspect of their lives and their comfort level(which is WILDLY separate from acceptance, understanding, belief, and knowledge) with the fact that men are emotional beings, find it easier to connect with women than men. If it's okay for a man to connect with women, why shouldn't he create friendships with them out of those connections? No reason at all because closing off is proved to be counterproductive to psychological and physical wellness and that closeness is not limited to family and partners. We all need friends and as a lady, you are probably aware that women kick ass. He seems to realize this too. Good for him.

SO!I said all of that to say this: there is a very distinct possibility that your boyfriend has a high number of female friends because he's an emotionally in touch human being who wants and values friends he can connect with emotionally but because of the way the current masculine paradigm socializes its boys from the day they're born, has a harder time making meaningful friendships with men than with women. Which is shitty because it shouldn't be so hard for men to open up to each other but according to all my guy friends? It is very very hard but it's much easier with girls. And the fact that male/female relationships have been romanticized and eroticized as the most acceptable way for a man to have strong emotions, to the point where you fear he will accidentally fall in love with someone else? Only stresses the point.

If he has a lot of female friends, and you believe him when he tells you they are truly friends (And why wouldn't you believe him when he tells you they are friends? Has he ever lied to you before? Has he given you a reason not to trust him? It's been two years. You don't have to like them or know them but do you know him, so you can use your best judgement there. ) chances are you may have to face the fact that he is a man who is more comfortable with female friends because of the reality in which we live. If so, the problem does NOT come from him or his friends or even from your jealousy itself but the structure of society as it currently functioning.

That in no way diminishes this problem at all or the pain you feel. What it does is changes what kind of solution your problem needs. If this is the reality of the source and type of friendships he has, then he's doing nothing wrong and you're doing nothing wrong - the world is wrong. But since you can't fix the world right now, if that is the source of your current problem, then your solutions become about acceptance and changing perspective and shifting your attitude and understanding. That sucks a big one because changing oneself is a much much harder thing to do than agreeing on phone calls and meeting times.

I think you were well on your way to the same conclusion. You came here asking to TALK about this issue, how to DEAL WITH YOUR JEALOUSY as a boundary, not tell him how to stop having friends. That's way more than I've seen people react to this sort of thing and considering the fact that you WERE yelling at him and now have moved forward to I statements and changing your own behavior, there is a very real possibility that you and your relationship are both having awful growing pains against the bounds of the existing very small heteronormative box of what you think interpersonal relationships should look like between men and women. You are bigger than those norms are and I think you know that because you seem very aware that your jealousy-based anxieties don't make sense completely logical sense. Because of that, I hope you will remember that we girls also get awful messages that poured into our heads from the cradle - in particular about Other Women as predatory competition, man-stealers, and that only way for men and women to meaningfully interact is romantically and sexually we are flooded with by movies and tv and the internet inescapably.

I'm sorry I dont have any specific suggestion about how to go about fixing your circumstances. I hope you'll consider these more abstract aspects when you're facing this very concrete problem. I don't have the whole picture but if it applies, I hope it may help give you a new lens with which to examine your feelings, options and possibly your situation as a whole.

  • Let us continue this discussion in chat. – Eff Jul 17 at 8:02
  • Comments are not for extended discussion; this conversation has been moved to chat. I can only do that once, so please use either this room or the one Eff made to further talk about this answer. – Tinkeringbell Jul 19 at 8:08
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    @RK a lot of people seem interested in the articles, and links you provided in the comments I now moved to chat. Since the best answers on this SE are backed up with references or personal experience (called expertise), would you be willing to edit your post and include your expertise? So, edit in the links, and quote the relevant bits :) That way people don't have to click a link to chat, and then another link to an off-site article to find these references :) – Tinkeringbell Jul 19 at 8:11

Alright... I am just going to start off by saying, I am that guy (not the OP's BF, but that archetype of men with close female friends).

I know men always say "oh I just connect more with girls", on the surface that's why, but there's a deeper reason than that. First of all, are all the girls cute and/or flirty with him? If so, think about why he doesn't have ugly female friends and you will get closer to the real reason why he kept all the attractive female friends.

I honestly didn't know why I was doing it until we went to couple's therapy (my then-gf at the time also had a problem with my female friends). I had a lot of close female friends, itt's to the point that my female to male friends ratio is probably around 3:1 or 4:1 and more importantly, many of them are previous lovers or flirty friends that didn't go anywhere. As far as I was concerned, it was great. I was happy enjoying the attention of multiple girls, but obviously she wasn't. My literal defense to her was "I knew them for a long time, we have a friendly bond that's non-sexual". To me sex is the only line in the sand that I won't cross.

While I did enjoy a strong bond with the girls and I don't want to give that up, I didn't think about... WHY? Why were there such a strong friendly bonds with them? After a lot of probing, the therapist and we figured out that it was ego-feeding. If you constantly have other girls trying to get your attention and say sweet things to you, it makes you feel confident, powerful, desirable; it's a great feeling and it even helps me excel in life (to the point that I have almost narcissistic level of self-confidence). Now that being said, there are emotional bonds (especially with ex's) involved, so when our therapist suggest that I write down reasons why I value those friends into a list of pros and cons, I find that most of my reason involve the physical attractiveness level of the girls; in another word, the same experiences I enjoyed with my friends would be LESS FUN if they were not attractive. I find that was probably the reason why I didn't have the same close friendship with girls that I don't find particularly attractive, which I took as the first sign that "Heyyyy, what's happening, that seems weird."

I found a lot of my best memories with these female friends are memories I would be too afraid to share with my gf at the time). I used to love going to breakfast with my friend slash an ex slash a colleague (she graphic designs for my company), the reason was she was a model and she dated a string of powerful wealthy men and she has impeccable taste. It feels very ego boosting when she looks up to me and holds on to my arm even if it's "just as friends". I had been told that I have a very flirty engagement approach to new female colleagues. Never had anyone not like it or said anything but I have a feeling that if OTHER guys had done the same thing, they (the girls) wouldn't be happy about it. I even have "romantic" dinner type things with the girls at work (the ones I find "somewhat" attractive).

Is it wrong? Depends on how you define wrong. There are a level of emotional involvement cause you know... I Am Human. But I only have sex with female friends when I am single, I would never knowingly hurt anyone close to me (like a current gf). When I said the same thing during therapy with my then-gf, the therapist correctly pointed out... "Did she not just repeatedly tell us how much she hated that? Do you not see that you are in fact hurting her?" So what I perceive as hurting someone is not the same as from that person's point of view, THIS IS THE KEY POINT to communicate to your bf as well. It doesn't matter if I internally justify it and tell myself "these are just my friends". Logical justifications notwithstanding, I was hurting my then-gf with my behavior

So when I thought about that... I ultimately decided that it didn't really matter if I find myself logically correct and subjectively justified in what I do, because it didn't matter to my then-gf. I correctly disengaged with all my flirty females friends, ended up stopping contact with about half (the ones who were ex's). I only kept REAL female friends (unfortunately, they were still too good looking for my then-gf taste), but they had bfs and/or is not in the city so she was finally ok with the ones I kept.

It was very hard because girls hold grudges. If you stop seeing them, they get mad and basically the bridge is burnt. Guys don't do that... If I haven't seen my male friend in 5 years and we then we will hang out, it's standard/default/expected; on the other hand, if I don't hang out with my female friend, I basically just lost half of my friends.

I suspect that your bf probably is in the same situation as I was back then. You can't argue with him and win logically because he had justified the existence of the girls in his mind already. If he had a logical reason not to hangout with them, he would have already done it. He didn't know why he prefer females friends (ego and attention) and he doesn't understand why you don't trust him. You just have to let him know that it's not about trust... It's about love and willingness to please. You are unhappy with that behavior, is that behavior important enough that he is willing to continue with it knowing you are unhappy? That was the train of thought that got me to stop. I knew I didn't need those ex-lover/paramours in my life, it's not worth the happiness of my then-gf at the time.

I hope your bf can see thing more clearly after you explain it to him. Good luck!

Being a civilized person means not acting on impulses in conflict with your code of ethics. It does not mean never having such impulses.

Obviously you cannot expect your boyfriend to never feel romantic attraction to any woman other than you, like it would be unrealistic to expect someone to never feel appetite while grocery shopping. But unless he happened to be starving, that should not make him lose control.

It will not likely work to make your boyfriend beholden to you by locking him away. Talk about and set your expectations about what each other is supposed to do rather than feel. This may also involve expectations about communicating changes of feeling that are recognized as being of more than transitory nature. You cannot make people responsible for their feelings (and thus you cannot base trust on them), but you can make them responsible for how they act on them. So talk it out, get to an understanding of how you expect the other to handle himself and how you expect to be trusted to handle yourself.

And when you find that you have been mistaken in your abilities of either, talk again. A dedicated relationship is both a boon and a responsibility, and sometimes a bit of love and trust can provide more of a payoff to the other than it costs.

How can I successfully let him know how I feel

I believe, from your description, that you already did - you told him, he got defensive; but he does know how you feel.

so we can have a productive conversation about boundaries without him immediately getting defensive?

You cannot. You should not. He will rightfully get defensive.

I assume it is pretty clear that there are implicit boundaries (e.g. no sex); I assume that he is basically happy to be monogamous with you, eventually to move in with you, have children and such. Even talking about this to him will be an affront to any sensible partner.

If you cannot trust him to respect this particular boundary on his own, then certainly there is no way you can talk to him to make him do so. If he were to have sex with them, then that would be a much larger "breach of contract" then him ignoring your plea not to have sex with them. So you can stop worrying about sex; it will happen, or not, and there certainly is nothing you can do about it if it does.

Making him spend less time with female friends may or may not lessen the chance that he has sex with them. It may increase it, what do we know (the "forbidden fruit", together with his resentment lowering your importance in his mind).

So, what else is problematic. Everything else is, well... just normal human interaction on different levels of emotional attachment. Do you really wish to "own" him? I do not believe that ever works, with anybody. Are you jealous simply because he spends time with them? Do you really wish to cut his ties to other humans? Would you mind the same if they were male friends?

As long as it does not impact you personally, i.e., as long as he spends as much time with you as you need, it should not matter how he spends the rest of him time, surely? He could be in the garage fixing his car/motorbike/bicycle on his own, or chatting with a group of male friends at the bar, or ... chatting with female friends at the same bar. What's the difference to you? Only yourself.

I don't know your friend, but I can guarantee from your short description of your interactions with him that if you make it confrontational, it will alienate him; either openly, or internally - the latter probably being even worse for you. It will probably make him more resistant to tell you about his friends; instead of being open, he will keep having his friends, but it will be more secretly. That is not something that you want.

So, my advice would be:

  • Trust him. Really trust him, without asking anything.
  • Work on being able to talk with him about his female friends just like you would about male friends - i.e., to stay on top of developments; are they studying? Are they traveling? Are they having good luck or bad luck etc.; those female friends are just humans.
  • If you have separate circles of friends (i.e., he would not normally tell you that much about his male friends either), then don't dig too much into the female ones; this will, again, come over as controlling and checking.

Source: I have plenty of contact with females, and my wife originally had a really hard time with it. We had scenes like a female colleague calling about work, my wife picking up the phone, and ... well ... us having several talks of several hours about my relationship to her. Let me assure you that it did not work as intended. I had nothing to hide, but there also was no way whatsoever to convince her of my innocence. It was very hard for her. There was no way whatsoever that this kind of discussion would have any positive effect for her.

Now, we have enough decades under our belt that this is all over now, thankfully. She knows full well that I have females that I am as close to as with males. After all that time, she knows that there is no sex or particular emotions involved. It took maybe 5 years or more, which were really unpleasant for her (but which I could not fix, really). My suggestion would be for you to take the quick route, start with trust, and accept them as just his friends, openly being happy for him to have friends in the first place. I know that this is harder for you, as you are before the children phase, but still, I am certain that it will be healthier for you to skip the constant nagging doubt. How you achieve that - that would be a topic for another question.

The relationship you want is between you and your boyfriend. As soon as you set boundaries between him and anyone else, you are actually the one crossing a line.

That said, it is extremely important that he understands your feelings on this matter. I think, though, that the solution will not be to restrict or alter his interactions with other girls, but rather for him to be aware of the situations you're uncomfortable with and how he can in those moments affirm his love for you.

The key here is to share your feelings with him in a way that evokes compassion an understanding in him rather than defensiveness.

So, when you talk to him, try to avoid ways of saying it that may make him feel blamed, or that he is doing something wrong, etc.

He may or may not be doing something "wrong", but that is besides the point. Your goal here is to make him understand you and have sympathy for your situation and your feelings. Since he has close feelings for you, this may come naturally for him. This sympathy and compassion for you may then naturally inspire him to change his ways, without you having to "confront" him at all.

So, when you talk to him about it, avoid saying things like "you are doing this and that, which is this and that".

Instead, express honestly how you feel about it, with as litte blame as possible. Explain to him that you know he does not mean anything wrong by it, but that is simply makes you feel sad. Describe this to him as sweetly and kindly as you can, and truly express how this is making you sad.

Hopefully this works. Otherwise, you may consider another approach. But this is what I would try first.

Your question:

How can I successfully let him know how I feel so we can have a productive conversation about boundaries without him immediately getting defensive?

Assumes that:

  1. He doesn't already know how you feel (he does)
  2. Knowing how you feel will make a conversation about boundaries to go better (yes, but see point 1)
  3. A conversation and/or agreement on boundaries will resolve the situation (it could work, but it doesn't address the real issue)

A man spends time with other women (swap genders as need be) because they provide him with something, no matter how trivial or innocent, which his/her main partner does not provide. It's a bitter pill to swallow but its a pretty simple deal.

You say he has many close female friends. My guess is that he's the kind of man who connects well with women on an emotional and intellectual level, and if he still seeks that out despite having you in his life (yes, you: the woman he is making himself be monogamous with despite probably not being that way inclined and having a multitude of other openings available) it means he is not getting that from you.

The good: If he is with you, it means he values the sum total of what you bring him more than the sum total of any of the other women he has available to him (despite not getting everything he would ideally like out of the relationship, but no one does). And it's not because he has these needs you don't fulfil that they will necessarily develop into interactions which are unacceptable to you. He could well be physically faithful to you all the way (so you might get your boundaries and he may well stick to them)

The bad: He connects with other women more fluidly than he does with you, and that's because you have fundamentally different views on life. It's written all over your question. He has many close female friends, meaning he's likely poly-amorous to a degree, pretty open minded with regards to relationships, and see the events as opportunities rather than threats. You on the other hand have signed up to a forum to ask strangers how best to coerce your boyfriend into sticking to boundaries so you can feel less threatened by other females (you use nicer language, but this is essentially what you're doing).

Hiding from that is going to end in disaster, the only way forward is to face this complete difference, accept that he will feel more intellectual and emotional connection with women who aren't you, and either cut your losses, or work with it. That is the only way you can "successfully... have a productive conversation about boundaries without him immediately getting defensive"

The ugly: no matter what deal you come to with him, you will always live in (quite valid) fear that he will one day meet someone he connects with so deeply that he will want to jump ship.

I may have got it wrong, but if you say he gets defensive straight away, and you feel it's an issue worth asking external advice on, then you perhaps both know deep down this is the situation you are facing.

His defensiveness is also quite likely due to resentment at passing on all those other opportunities out of respect for you and to keep you happy in your desire for a monogamous relationship, so he feels he's already "doing you a favour" by not screwing around when plenty other men do. That might sound harsh, but you need to remember there are plenty progressive and open minded women out there who don't see emotional connections their men have with other women as a threat, who accept that humans are what they are, rather than forcing the world to fit moral notions of what they should be, and who deal in trust and honesty, not boundaries. And he will have met such women.

Of course, the only sustainable solution to all this is for you to become such a woman yourself. Once you start accepting that you are perfect just the way you are then you stop looking to external validations as a substitute (such as success in a relationship) and stop feeling threatened by things which threaten these flimsy substitutes (such as your partner being close to other women) and stop trying to control things you have no place controlling (such as placing boundaries on another conscious being's rights). You'll find that your man feels closer, less judged for being what he is, less inclined to spend time with other women who make him feel that way, and you'll feel less threatened by the time he does spend away.

I will try to give the perspective of somebody who has mainly female friends and my girlfriends/wife had such conversations with me over the years.

but I can't help but be afraid that he'll unknowingly cross some emotional line and become too close ...

it seems like he should have respect for me enough not to put himself in potentially compromising situations

My main issue is with these sentences. Focus not so much on "avoid situations in which things which you can not accept could happen" but focus on what you consider to be such things.

You have to see it simple: If you boyfriends wants to lie to you, he will. If he is honest and faithful, then in my experience people do not fall naked on top of each other. In the first case the conversation will lead to nothing. in the second case, you should focus on the things which would make you feel bad, and state these.

Think about e.g.

  • the two drinking a cup of tea privately and talking for a few hours until 3am
  • the two holding hands to support each other emotionally.
  • the two sitting close on the sofa (without further body contact)
  • the the two stroking each others back and holding each other
  • giving each other a massage
  • falling asleep together (without being naked)
  • giving each other a single kiss on the cheek

All of these are things which happened between me and my close female friends, and it never lead to us petting or having sex. I understand for every level that my SO could feel uneasy, and I am willing to respect that, but if SO says "drinking tea is leading to potentially compromising situation" she would be questioning my own ability to control myself and stop at what is really a problem.

For example, instead of forbidding a close friend of mine to sleep in the same room as me my wife plainly stated the boundary that I should not share a bed with this friend (which was anyway not our intention).

I think it would help a lot if you just talk to him about how this friendships started and what these mean to him. If you develop a mental framework with him, then I think it could make this conversations less about your fears and more about what make you feel bad if it happens.

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