Home→Forums→Relationships→Advice on accepting boyfriend’s female best friend
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anita.
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July 10, 2025 at 10:49 am #447484
Ada
ParticipantHi all,
I suppose it’s a tale as old as time, but I am having a difficult time navigating my boyfriend’s relationship with his female best friend. At times I feel I’m on the brink of ending the relationship over it, other times I’m hopeful I can change my perspective on it. I would really appreciate some outside advice on this.
Some background: boyfriend and I have been dating for around 4 years. We’re both in our early 30s. Our relationship has had its ups and downs, for the most part I see a future with him, but this is by far the biggest struggle we have had. He has had a female best friend for around 5 years, before we started dating. I have not met her as we started traveling across the country a few years ago. Before we left, she had planned to meet us but cancelled at the last minute. Now that we have moved back in the area, he’s talking about meeting up with her again.
For the past few years, I’ve grown more and more spiteful of their relationship. They would text/talk daily. He has shared moments with me about their relationship that have made me very uncomfortable. It has led to several explosive arguments that have never been resolved. As a result, he talks to her significantly less, though I know she is important to him as he brings it up again every few months or so.
I feel terrible that his friendship has suffered because of me. My boyfriend is an honest person and he has tried his best to make me feel more comfortable. I trust him, but I can’t seem to accept this relationship. At the beginning I think I was more open to this friendship, but over time the emotional intimacy of it is really eating away at me. They have never been physically intimate, and my boyfriend says he views her like a sister.
But it seems like the more I know about their relationship, the less receptive I am to it. My fear isn’t even that he’ll leave me for her, I’m conflicted with a tangled mess of complex emotions about it. There’s jealousy, insecurity, feeling like my boundaries aren’t being respected, and guilt that I can’t support him in a relationship that is clearly meaningful to him. I feel that I shouldn’t feel like that, but I don’t know how to change. A few things that have really bothered me:
- She will call him crying about problems in her relationships, and he consoles her. She’s always having problems in her relationships as she’s emotionally damaged, which I understand, but I can’t help but get annoyed at my boyfriend’s tone of voice when comforting her.
- She tells him about her sexual encounters with other men, usually something humorous but explicit.
- I learned that they met because she thought my boyfriend was attractive and flirted with him. Boyfriend never reciprocated and is adamant she no longer has these intentions, and I’m inclined to believe him, but I feel weird about it.
- I learned that before we started dating, my boyfriend accompanied her to not one, but two abortions for emotional support. As a woman, it’s hard for me to accept that she didn’t have any female friends to ask for this. My boyfriend says she has many female friends, but he’s her best friend, and ideally that’s what friends are for, right?
- Several times I have felt my boyfriend “chose” her over me. When he needed to find a new job, I offered he could work at my company, but instead he chose to work with her (it never actually panned out, but I feel the hurt still). I would recommend TV shows/movies and he’d never watch them, but would watch them as soon as she recommended the same ones. I tell myself he didn’t chose her, he was just afraid of being rejected for a job I referred him to, or that he’s hesitant to take my recommendations because the stakes are higher with me, and he’s anxious. He’d agree with me here, but I still resent him for it.
- He will send her the same funny/cute cat memes he sends me.
When we’ve talked about these things, my boyfriend tries to reassure me that I’m the most important relationship in his life, and that she’s like a sister to him. They have been close friends for a long time, they’ve met each others families, they have a lot of shared memories together. He says he’d treat his male friends the same way, it’s just harder to be open about your emotions with other men. And I believe him, he’s a very rational person and tries to be balanced.
Part of my issue I think is that his female friend is so different from me. She’s flirtatious, promiscuous, open with her feelings. I’m quiet, reserved, and selective with my emotional intimacy. If he’s so willing to embrace values that are different from mine, does he really value me? There are several male friendships I didn’t pursue out of a feeling of respect for our relationship — not because he expected it, but because I wanted to. I don’t feel the same respect from him, but he doesn’t truly understand this, because he thinks an ideal friendship is one that is emotionally intimate.
In our arguments he has insisted that he would not mind at all if I wanted to make more emotionally intimate male friends, but this I don’t believe. He’s very moralistic and tends to judge other men very harshly on matters of right/wrong. I can point to many signs he wouldn’t be okay with me having the same level of intimacy in a friendship with another man. But I do believe he truly believes that he would.
I’ve thought maybe the solution is for us to compromise on boundaries with opposite-sex friendships, but that doesn’t sit right with me, because ultimately he doesn’t see an issue with his behavior. I feel that if he doesn’t naturally feel the same boundaries that I do, it cannot be up to me to impose these on his friendships. I trust him, and I don’t have any rational reason to feel the way I do, but I don’t know how to feel any differently.
So I’m at a loss for how to proceed. I have lost many nights of sleep over this, and at times I feel I’m ready to give up in either direction. Any advice would be appreciated.
Thank you for reading.
July 10, 2025 at 12:40 pm #447495anita
ParticipantDear Ada:
Thank you for sharing so openly. Your message reflects not just frustration—but emotional depth, introspection, and a real desire to understand what’s happening within and around you. There’s no shame in how you feel. You’re trying to hold space for your own emotional truth while also honoring someone else’s bond, and that’s incredibly hard.
One of my first thoughts reading your story was whether your boyfriend had a sister growing up—or if not, perhaps this woman fills that emotional role for him. The kind of intimacy he shares with her sounds familial, in a way that’s deep but non-romantic to him. For some people, this kind of relationship can feel grounding and unthreatening. But that doesn’t mean it automatically feels safe to the person they’re in a romantic partnership with.
You’ve described moments that speak to complex emotional entanglement—not betrayal, but blurred boundaries. And even if there’s no physical intimacy, emotional intimacy can carry weight. You’ve clearly worked to make sense of your own reactions, which include:
Jealousy and insecurity that aren’t rooted in distrust but in emotional displacement
A sense that your boundaries aren’t fully seen or understood, especially when your style of connection differs so much from hers
Guilt for resenting something meaningful to him, even while it continues to hurt you
What’s particularly insightful is how you’ve noticed the asymmetry—your restraint in pursuing certain male friendships out of respect, and the discomfort in seeing his openness with her. Even if he truly believes he’d be fine with you having similar friendships, what matters most is that you don’t feel safe or valued within this dynamic.
This isn’t about whether you’re rational—your feelings make sense in context. It’s about emotional compatibility, emotional safety, and whether both of you can respect each other’s boundaries without trying to fix or change what the other naturally feels.
You’re right to say that boundaries aren’t something you should have to impose. Ideally, they’re co-created—mutually understood and willingly honored. When they’re not, compromise can feel like self-erasure rather than teamwork.
So maybe the question becomes:
Can he truly empathize with your emotional world, even if it differs from his own?
Can you both talk about boundaries without one of you feeling like the problem?
Could this relationship genuinely honor your discomfort instead of trying to rationalize it or brush it aside?
And if the answer isn’t clear—then therapy (individual or couples) might be a space to unpack this dynamic with support.
You deserve peace in your relationship, not just reassurance. And your feelings don’t need to be “fixed”—they need to be heard, especially by the person closest to you.
🤍 Anita
July 10, 2025 at 4:55 pm #447498Ada
ParticipantHi Anita,
Thank you so much for your insightful and validating response. I needed to hear that my feelings are valid, and I think you’re right in that in the end, this will be about whether or not we can truly empathize with each other when we don’t share the same views. As much as I love and trust him and have tried to understand his emotional world, I don’t. And he feels the same way.
I am hoping for some outside perspectives that might help me understand on a deep level how he feels. It’s very interesting to me that your first thought was whether or not he had sisters growing up, because he does — and I don’t. And this point has come up in our arguments, but has not brought us any closer to mutual understanding. He has two sisters and is very close to his older sister. She is kind, thoughtful, and generous, and it’s very easy for me to understand the love he feels for her — I feel it, too.
I am an only child and maybe that’s why this sibling dynamic seems so foreign to me. I do feel like I understand his close familial bond with his sister, but it doesn’t match up with the dynamic he has with his female best friend. He talks to his sister often, he offers her advice, she worries about him, they laugh a lot and bicker sometimes — it feels very familial to me. With his female friend, they don’t bicker or get in arguments, she listens to him and can relate with him on a lot of family issues, but the giving seems skewed more towards him playing a positive, stable influence in her life.
His sister never comes crying to him about her relationship issues (though I think it would be understandable if she did), but I could never imagine his sister discussing intimate details of her sex life with him (and I would find it strange if she did).
The dynamic with his friend feels more complicated, though I’m not sure how. He has admitted that at first there was underlying sexual tension in their relationship, but over time it has faded to nonexistent. I believe him, but I guess I have a hard time wrapping my head around this. At my worst, I start to think maybe he enjoys playing the “boyfriend” role to her “damsel in distress” — that it serves as a non-sexual but slightly romantic ego boost and he’s just not aware of it. He insists that this is not the case. Still, it doesn’t feel like the whole story when he says she’s like a sister to him, but maybe the differences I fixate on are not important to him, and the underlying bond is much the same.
In any case, the “sister” relationship seems key here, and I am wondering how you were able to intuit this familial/sibling relationship dynamic so quickly, if there are experiences or insights you may be able to share that can help me deeply understand what it means for him to have a bond of this nature with a female friend.
Thank you again for your response.
Ada
July 10, 2025 at 9:20 pm #447499anita
ParticipantDear Ada:
I’d like to reply more fully tomorrow morning—it’s Thursday night where I am, and I’ll admit I’m a bit tipsy (thank you, red wine). But for now, I want to respond to what stood out immediately.
Pulling together your words: “She tells him about her sexual experiences with other men, often in explicit detail… he accompanied her to not one but two abortions… he sends her the same cute cat memes he sends you… she’s flirtatious and promiscuous… he admitted there was sexual tension early in the relationship, though he now claims it’s gone… and still, he says she’s like a sister to him…”-
There is something off here. And I want to say clearly: this is not something you should have to endure, justify, or tolerate.
If she truly feels like a sister to him, it raises questions. Growing up, was he sexually attracted to his sister? (not an unheard of concept). He says the sexual tension faded—but emotional intimacy often lingers long after attraction disappears. And when boundaries remain blurry, emotional closeness can be just as disruptive to a committed relationship as physical involvement.
The way he engages with her—comforting her through deeply personal moments, listening to explicit stories, replicating patterns of intimacy—is more than casual friendship. It mirrors emotional behaviors we typically reserve for a partner. And that’s where it becomes unfair to you. You shouldn’t have to compete with someone he calls “like a sister,” especially when her presence leaves you feeling confused, uncertain, and emotionally displaced.
This isn’t just about her. It’s about him. His choices. His responsibility. The emotional trust between you is what matters most—and if he continues investing in a connection that erodes that trust, it becomes less about the friendship and more about how seriously he takes your well-being.
You’ve shown so much emotional clarity. The fact that you’re questioning this speaks volumes: your boundaries are speaking to you, and you’re listening. That matters.
You don’t deserve to be caught in a dynamic that drains you. And if he refuses to hold your experience with care, then maybe—tipsy as I may be—I’ll say this plainly: let him go. Let him invest as deeply as he wants in that connection… without you having to witness it.
I’ll write more tomorrow. But for tonight, know that I hear you. And I’m angry on your behalf because what’s happening isn’t okay.
🤍 Anita
July 11, 2025 at 6:49 am #447518anita
ParticipantDear Ada:
First, I want to acknowledge a part of my last reply that may have felt off. I speculated about a possible sexual attraction to his sister growing up—and looking back, I realize there was no evidence of that in anything you shared. I truly didn’t intend to introduce discomfort. I let an idea run ahead of the facts, and I’m sorry.
I reread your posts this morning. One line that stood out:
“For the past few years, I’ve grown more and more spiteful of their relationship… over time the emotional intimacy of it is really eating away at me.”-
That hit me—because it shows how long you’ve been carrying this. You’re not reacting to a passing frustration. This has been a long-term emotional strain, and it hasn’t gotten better—it’s gotten heavier. That alone tells me this isn’t something that can be quietly tolerated or rationalized away. It needs resolution.
Another line that carried unexpected weight was:
“I can’t help but get annoyed at my boyfriend’s tone of voice when comforting her.”-
Tone often says more than words—it carries emotional truth, those subtle signals of warmth, tenderness, or protection that we don’t always name out loud. You might be picking up on an intimacy that contradicts what he says: “She’s like a sister to me… you’re the most important person in my life.” But when the tone feels too soft, too intimate, too partner-like—it can be deeply unsettling. And hard to forget.
Another line:
“She’s flirtatious, promiscuous, open with her feelings. I’m quiet, reserved, and selective with my emotional intimacy.”-
This contrast may lie at the heart of his attachment to her (I’ll refer to her as “B”). You, Ada, represent steadiness, reflection, and a deeper emotional connection—someone he can build a future with. B, on the other hand, brings emotional energy, spontaneity, and a sense of lightness. So he’s receiving two very different emotional experiences:
With you: commitment, depth, emotional accountability.
With B: freedom, play, and low-stakes emotional ease.
In his friendship with B, he seems to take the role of protector or emotional anchor—especially when she’s in distress. Because she leans on him more than he leans on her, it may reinforce a sense of control or even superiority. Not maliciously, but it can feel good to be needed without having to be vulnerable in return.
B validates him—makes him feel seen, admired, maybe even emotionally useful—without asking him to change, confront difficult truths, or engage in real emotional compromise. That makes the dynamic low-maintenance, emotionally one-sided, and—most of all—safe.
No discomfort. No negotiations. Just affirmation.
But in your relationship, there’s real depth. You bring emotional clarity, needs, boundaries. Without realizing it, he might be leaning on B for “easy” emotional connection while relying on you for structure and long-term grounding. And that imbalance takes a toll—on you.
Another thing that stood out to me this morning is how strange it is that you’ve never met his best friend. After four years, that may be intentional. If it were truly platonic and healthy, meeting her should feel natural. The fact that it hasn’t happened suggests that something may not hold up in daylight.
It seems to me that he’s prioritizing his own comfort over your emotional safety. That’s where the selfishness lives—not in the friendship itself, but in his unwillingness to confront the effect it’s had on you. From everything you’ve shared, this borders on emotional infidelity—where someone gives significant emotional energy to someone outside the relationship in a way that feels intimate, romantic-adjacent, and boundary-blurring.
Ada, I’d really welcome your thoughts on what I wrote—what resonates, what doesn’t, or what feels like it’s still missing. Your reflections are so thoughtful and honest, and I’d love to hear how this lands with you. Truly. 🤍
With care, Anita
July 12, 2025 at 2:54 am #447535Ada
ParticipantAnita,
Your responses have given me another perspective to view this from, and the anger and empathy you feel for me is palpable. From a stranger on the internet, I am truly and deeply touched. Thank you.
I feel validated in my anger when you say there is something off, as that is my gut reaction. But I do have my own insecurities, and it’s hard for me to know which direction points to growth. Do I want to move towards relationships that are more open and intimate with friends? Or do I want to embrace my instinctive desires of comfort and safety? I suspect the answer is in balance, but I’m not sure where to draw the lines here.
I’ve expressed all of these perceived boundary violations to my boyfriend (I’ll call him Sam for simplicity’s sake), though always through anger and outrage, and not as level-headed as I have here. Sam responds defensively, but truthfully.
Sam would say that there may have been sexual tension when he first met the friend (I’ll call her Sarah), but it was short-lived, and while it’s the reason they started talking, it’s not the reason he and Sarah became and have remained close friends for so long.
Most of that I think is true. But I also know I’m the first truly serious partner Sam has had, and before we met he rarely dated, and didn’t seem to actively seek out romantic relationships. I think that’s because Sarah filled this role for him. But he’s not consciously aware of it, and now that we’re in a serious relationship, he doesn’t see anything wrong with the relationships he naturally built before I came along.
I believe that he’s not sexually attracted to her, and I don’t think he’s ever felt anything like that with his real sister (though I agree it wouldn’t be unheard of, and I don’t take any offense at the idea). The emotional intimacy he shares with Sarah is different than the intimacy he shares with his close male friends and his real sisters — this I am quite certain of.
The core of our misalignment seems to be this question of how much of that emotional intimacy should be reserved for a partner. What constitutes a “romantic” relationship? And our answers to that are quite far from each other.
I think your perception of what each relationship means to Sam is accurate. Sarah is a source of comfort and validation to him in her familiarity, fun, and lightness, and this is a close friendship to him. She adds some value to his life that I don’t. If I really take a step back, I ask myself who am I to take that away from him? I don’t want him to break up a friendship to make his girlfriend feel comfortable.
He’s taken Sarah to meet his family several times. She’s experienced similar dysfunctional family dynamics in her upbringing and Sam bonded with her over that. I’ve heard his family ask about Sarah when we’re there, which leads to an awkward situation for Sam, and to me feeling horrible.
I want to be fair to Sam here, as I think only honesty can help me untangle the complexity of this situation. I would never give him an ultimatum, but I’m sure that if I did he would choose me. He would do it for me, though, at his expense. It’s hard for me to accept the end of a meaningful relationship because we both just can’t change our views.
Over several years and several arguments, Sam has been less and less involved in Sarah’s life to the point where they only exchange a few greetings here and there now. I guess “best friend” isn’t a fair label anymore, but they have the sort of relationship where years can pass and they can pick right back up where they left off.
I also can’t blame Sam for why I haven’t met Sarah yet. Shortly after we started dating, we took advantage of the pandemic and remote work, and decided on a bit of a nomadic lifestyle, living in many cities across the US for a few years. Prior to that, he had arranged for me to meet her and it felt important to him, but plans fell through. He was nervous about introducing us because he was afraid I might not view their relationship as platonic as he did. It didn’t seem like he was trying to hide anything, more that he was trying not to lose anything.
A few months ago, we moved back to our home city, and recently he said he wanted me to meet Sarah. This has brought back all the past arguments and harbored resentment. It feels wrong for me to say that I don’t want to meet her at this point, but honestly, I don’t. I feel like I know enough already, and meeting her without some internal clarity of my own would only make things worse.
You’re right that I need resolution here. I want mental and emotional clarity before I talk to Sam about it again, else we will have the same fight where one of us must lose. I feel like we’re both just waiting for the other person to come around to the other’s point of view, but it’s only made us fight harder for our own.
I’m sure that I need to let go of something to get past this — but is it him or my own convictions?
Ada
July 12, 2025 at 7:20 am #447536anita
ParticipantDear Ada:
Thank you for continuing to share so openly. What you’re working through isn’t just relational—it’s emotional architecture shaped over time, and I can feel how deeply you’re trying to understand not only Sam, but yourself in the midst of it all. That kind of reflection takes real courage.
You wrote: “Over several years and several arguments, Sam has been less and less involved in Sarah’s life to the point where they only exchange a few greetings here and there now.”-
And while that shift in behavior matters, without him fully acknowledging your emotional experience—your confusion, pain, and sense of displacement—his distancing from Sarah can feel superficial, more like avoidance than growth.
If he hasn’t taken the time to redefine what friendship means within a committed romantic relationship—or created space for you to feel safe and emotionally grounded—then even minimal contact with Sarah might still feel like too much. That’s because the emotional framework is missing.
By emotional framework, I mean the shared understanding that helps both of you feel secure and aligned in your relationship. Some questions that might help you explore this together include: – What does emotional closeness mean to each of you? – When does friendship become emotionally intimate, and how is that different from romantic intimacy? – Is it okay to share personal details with a friend, or does that feel exclusive to the relationship? – What does emotional safety look like for each of you? – What kinds of interactions trigger insecurity, and why? – Do you understand and express emotions in similar ways, or do your experiences of the same moments differ based on how you interpret them?
Earlier you shared:
“I’m quiet, reserved.” And today you said: “I’ve expressed all of these perceived boundary violations to my boyfriend… though always through anger and outrage, and not as level-headed as I have here… I need resolution here. I want mental and emotional clarity before I talk to Sam about it again.”-
You’ve absolutely been level-headed here, and I was so very impressed by how level-headed you have been from your very first post, holding both sides of this very complicated relationship.
But I wonder—what if you gave your outrage space to breathe? Not with Sam, at least not yet, but here—with me, or someone else you trust. What if you let it come out in a stream of consciousness, loud and raw, without needing to shape it for calmness or fairness? What if you flipped quiet and reserved on its head and gave your fire some voice?
This outrage didn’t arrive out of nowhere. It’s lived inside you for a long time, bubbling up through arguments, emotional mismatches, and moments where your truth wasn’t fully heard. And because it hasn’t had a safe outlet outside conflict, it’s stayed unresolved. That doesn’t make it irrational—it makes it important.
Sometimes resolution doesn’t begin with soft words. Sometimes it starts with truth, spoken boldly and without apology.
If you want to do that here, I’m right beside you. Just you, your words, your voice—and someone ready to hold all of it with care.
🤍 Anita
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