Should I hook up with my best friend’s brother after years of history and tension?

This is going to be long. Like, really long. I’ve never told this story fully, and I don’t want to hold back any detail, because every part of this feels important, even if they felt small at the time.

I’m 26 (f) now. He’s 25 (m). We met when we were teenagers at summer camp. I think I was around 15 or 16, and he was maybe 14 or 15 I don’t really know. I stopped going to camp when I was 17. That means we spent a solid few years seeing each other every summer for around 8 weeks straight. Camp was kind of a world of its own there were no phones, no internet, just time spent with people. And from the beginning, there was this unspoken something between him and I . tension, A vibe, comfort. Something we never named, but both clearly felt.

Looking back now, I realize just how flirtatious andphysically drawn to one another. But I didn’t realize it then. I was a virgin for all of those years. Not just physically like emotionally too. I was Naive/Oblivious. Like, if you didn’t say directly to my face, “I like you,” I wouldn’t know (I’m still like this). And I wasn’t flirting with boys or dating at all. So I shut that part of myself off. But the tension was there. All those summers, we’d cuddle in our bunks, hold hands, talk for hours just the two of us. It didn’t feel weird. It felt like us.

But there were always these moments between us.

Like the time we were doing an activity for the younger campers, and he randomly put a cardboard box over his head and leaned in and kissed me on the lips through it. It was playful, but also like… what the hell was that? Again I was confused because he was openly talking to a girl at camp?????

Or the night we went skinny dipping with a group of friends. I floated off by myself in the water, and out of nowhere, I realized he was behind me. I didn’t notice him swim up. I said something like “Whoa, when did you get here?” and I remember he kind of backed off when he saw I got uncomfortable. I wasn’t scared of him or anything at the time I was just inexperienced. He didn’t push anything. And again, nothing happened, but it felt like something.

There were other moments too. Like years later, during a family vacation. ( His parent are Canadias but they were born and raised in the us, so he has dual citizenship and travels between the U.S. and Canada. That’s why he was visiting.) I was invited on the trip, since I’m close with his sister she’s my best friend.)One night, he and I were watching something on my phone while cuddling, and I backed into him without realizing what I was doing… and he kept shifting away. I found out later that he had a hard-on. I didn’t notice at the time. (Again: I was still a virgin, still completely clueless about all of this).

Another time, during his high school graduation, I visited and we were just hanging in the basement. I was lying on his lap while he did homework. Just regular stuff to me, but like… why was I lying on his lap? Why was that so normal between us? Why did it feel so natural but we never spoke about it?

It wasn’t just physical stuff. We’d talk deeply. About our lives, our sadness, our families. We’d been there for each other through hard things like depression, breakups, transitions. Even when we stopped going to camp, we’d talk off and on after every summer for a few months. The pattern was always the same: we’d reconnect, flirt, vibe, and then maybe see eachothee once that year and then life would happened again. He’d have a girlfriend. I’d be in a relationship. Then there were longer gaps. Especially post-secondary and during the pandemic. I couldn’t visit them in the States, and he couldn’t come here.

But the connection never fully died. EVER

His sister (my best friend) noticed it. Especially on that family trip. She wasn’t weird about it. Just… aware. She once told me, “I don’t care what’s going on between you two, just be honest with me.” I love her so much. She’s important to me. And honestly, even though she and her brother are close, he doesn’t think she needs to know anything now if something were to happen. I get it, but I’d still want to tell her. And maybe not EVERYTHING. That bond/Trust matters to me.

We never openly talked about our chemistry until recently. Just a few weeks ago, he finally said something that acknowledged the tension. And everything shifted. Our conversations are different now. More open. More sexual, yes, but also still that same comfort. It’s familiar. And exciting. And confusing. And that maybe be because its over text idk

He’s currently planning a road trip through the U.S. and into Canada, and there’s a chance he’ll come see me. And for the first time ever, the possibility of hooking up is real. In and environment were its just completely me and him…

I haven’t hooked up with anyone in over a year. I haven’t liked anyone, like really liked anyone, in almost three. And ALL the sexual experiences I’ve had were disappointing. But I keep wondering… would this be different? Would it finally feel good, satisfying, connective? Would it finally make sense? Would I not hate it?

I’m trying not to idealize it it too much, but it’s hard not to. The emotional tie between us started in some of the most formative years of our lives. I went through puberty knowing him. We’ve grown in and out of each other’s orbit for twelve years. That kind of familiarity is rare. And I know his family like I call his parents mom and dad.

I don’t know if this means anything to anyone but We’re both Cancers. We feel deeply. And when I talk to my friends about all this, even though I’m in my man-hating era, they tell me I seem brighter. More giddy. Especially about a man They say, “This is so you. Our story, Our dynamic it’s one-of-a-kind. You should see it through. Even if it’s just to close a chapter or understand something about yourself.”

Maybe that’s true. I think I do want to experience it, not for closure, or for the plot: shits and giggles, but for clarity. Because there’s always been a “what if.” And for once, that question doesn’t feel scary. It feels right and okay.

Right now, he’s showing interest. He’s been answering every question I throw at him with honesty and confidence. There’s no confusion on his end. He admitted he’s always found me attractive from when we met at camp. And I don’t feel like I’m entertaining him or being used. I genuinely want it, too.

But still… I don’t know what happens after. I don’t know if I’d want more if he said he did. I hate long-distance. And I’m not looking for a relationship. But this isn’t just a hookup. It’s a 12-year-long thing that never quite became a thing and now maybe it finally might.

So yeah. That’s where I’m at.

We haven’t done anything yet. But the moment is close. And I’m scared, excited, curious, emotional, and… kind of hopeful.

But there is a part of me that’s a little wary.

He got out of a relationship around six months ago. I don’t know the full story. He hasn’t said much about it yet. His ex is still in a few pictures on his profile, and his family still follows her. I did ask him about it, I’m waiting to hear what he says. But I’ve felt nervous even bringing it up around his sister (who’s my best friend), because I don’t want to accidentally reveal something about our situation before I know what’s really going on.

And to be totally honest… I think he might be a bit of a relationship hopper. Like, someone who doesn’t always give himself time in between. And I guess that’s what I don’t want, I don’t want to be some rebound, or emotional filler, or someone he just latches onto because he’s used to being in a relationship. I care about him, and I care about me, and I want this to be a genuinely positive experience. Not something rushed, not something that turns messy because one of us isn’t ready.

Especially because we’ve known each other so long. I want this, especially the sexual side of it, to come from a place of mutual choice, not emotional leeching. I want this to be intentional.

TL;DR
We met at summer camp 12 years ago. Always had insane chemistry but never admitted it. We were both young, I was a virgin and naive. We cuddled, held hands, talked deeply, but never acted on it. Recently we finally admitted the attraction. He might be visiting me soon and there’s a real chance we’ll hook up for the first time. It’s not just sexual, it’s deeply emotional too. Not sure what will happen, but I’m open, curious, but also scared.

My questions are:
1. Should I tell my best friend (his sister) before he visits, even if nothing’s happened yet?

2.  Am I overthinking this, or does it sound like a bad idea to go through with the hookup?

3.  If I do go through with it, how do I set emotional boundaries to avoid getting hurt?