Advice on navigating a new relationship where my boyfriend has a longtime female friend whose bond with him feels almost like a romantic partnership. How should I respond to the month-long winter trip they’re taking together – with her boyfriend included – especially since I can’t join them for the full stay with the three of them at an Airbnb and will likely only visit for a long weekend?
Or regarding future trips?
Context:
They met a decade ago in college, share hobbies and interests, and go on at least a few trips together (sometimes with just her and her partner so the three of them, and for extended periods of time away).
Significantly, she fits many of his “standards,” and they have so much in common that they could’ve been college sweethearts. When they met in college, he was attracted to her (he admitted to having sexual attraction). It’s also likely he wanted to ask her out, but she got into a relationship with someone else – lost her virginity to that person.
He gave up on asking her out, but she has been, and still is, a core part of his friend group and social life, so she’s deeply integrated into the people and activities he spends most of his time with, except for a few years when she wasn’t living close by. He believes he can separate attraction from friendship and that it’s not overstepping because the hangouts are usually with her boyfriend too. But their closeness is almost partner-like, just without the sexual side. He talks about her often, goes to her for emotional problems, reminisces about shared memories, buys her gifts, and they celebrate each other’s wins — basically, he claims they have a special bond.
He’s been single this whole time (just casual dating here and there) and is finally dating seriously, being in his 30s and whatnot. Nonetheless, when I asked directly if he’d be open to dating her if she showed interest, he hesitates for a while before saying no, like there’s still some lingering feeling there. He mentioned that she might have liked him at some point, but she would’ve shown it since she’s not the type to avoid pursuing someone she’s interested in.
TL;DR
Boyfriend has a long-standing, emotionally close friendship with a woman he was once attracted to, and their bond resembles a romantic partnership in many ways. They’re planning a month-long trip together with her boyfriend. Wondering if this is healthy for our relationship given their history and level of closeness.