My (27m) best friend (27m) has been pursuing my (21f) sister for 3 years and I need outside perspectives?
My best friend rented a room off of me, and is my employee - we work 2 weeks on, 1 week off. While my wife and I were on our honeymoon, my best friend was scheduled to work (so he’d be gone 2 weeks) and we needed someone to watch our 2 cats while we were away so I called my sister and she agreed to stay at my place while we were away until my friend was back from work.
At this point, he and I were 25 and my sister was 19.
He got back from work and we noticed on snap maps that she hadn’t left our place yet so we knew something was up, but after our wedding, love was in the air and even though morally I disagreed with it, I decided that it wasn’t my place to control the love life’s of those around me. He thought he was sly and that no one knew but after a couple clever comments from my wife he realized he was busted and finally spoke to us about it. I said I’m only okay with it if it was what my sister wanted and that I didn’t like the thought of it unless it was her idea.
Eventually this fizzled out, and my wife and I were relieved. But then it happened again, and again, and again. Fizzling out each time, but each time putting me through an emotional rollercoaster.
Fast forward to 2025.
In 2025 I received a phone call from my older brother (30m) saying my sister had reached out to him talking about how my friend was making her uncomfortable and that she was trying to end things and that he was just being pushy and not taking no for an answer when it came to her hesitation about their relationship. He gave me shit for letting this happen in the first place. He was right. This marked the turning point where I went from a laidback-ish view and switched to being the most unsupportive person in regard to their situation.
After my sister got everyone involved we got together to discuss things and how it was probably better to not give any more time or effort into trying to make that relationship work. Everything stopped, thankfully. At this point in time I should’ve pulled my friend aside and made boundaries, highlighting where he went wrong and why it’s not going to happen going forward. This is where I failed as an older brother. I assumed that given how she was uncomfortable that she wouldn’t talk to him anymore, saving me that awkward conversation, but I underestimated how desperate and persistent he truly is.
Turns out, he never stopped trying. Living under my roof, hitting up my sister non stop. All in the name of what I said years before “as long as it’s what my sister wanted”. I guess in his mind he heard that as “as long as I can convince her she wants it” missing this point entirely.
Fast forward to 2026, I get a call from my sister before my cycle and she says to me that she thinks she has feelings for my friend. I expressed my disapproval but had to leave for work so didn’t get to speak to her as much as I wanted to. A couple days after on our way back to the crew house (which we live in together) from work one day he says “I’m a people pleaser, and I do everything for everyone else all the time (which btw is completely deluded self assessment) and so I’ve decided to do something for just me” and that thing was dating my sister. I completely lost my mind and spoke to him in a way that I’ve never spoken to a friend before - making it very clear that I wasn’t on board. My mistake of not setting boundaries after the last time just keeps playing over in my head.
My sister got cold feet after her and my short phone call and she told him that she isn’t into if I’m not on board, so he hid our conversation from her, lied, and told her that him and I were all good with no issues. So she obviously upon hearing this was back on board.
At hearing these lies I called my sister over once I got home to put everything on the table, I told her about where I failed as brother and that I should have made boundaries after he made her uncomfortable last time. She said that knowing how I really felt about it changes everything, she thanked me for being honest, and said that she understands. She ended things with him the next day. She said that in between every time they tried that he never stopped messaging or trying to be in a relationship with her, which goes against what he was telling us the whole time.
As long as they stay in contact, he’s not going to get over her and he’s not going to stop trying. My plan now that it’s over between them is to tell him that he can choose to stay in contact/pursue my sister if he wants, but that I can’t in good faith stay friends with him if that’s his choice given all the history.
(For more context, we’ve been best friends for 11 years, and he rented a room off of me in my house for 6 of those years, he stopped renting from me when he bought the house across the street and we are now neighbours. I got him a job at the last 2 companies we’ve worked for, and have been his boss for 5 years, and like I mentioned above we even live in the same house while we are out at work for our 2 weeks on 1 week off so there’s not much getting away from him.)
I just feel this whole thing is cusping the edge or predatory and manipulative, please tell me where you think I went wrong or if you think I’m on the right track.