A bad situationship from four years ago is hurting me still

Four years ago I (27M) was in a pretty rough situationship thing with a family friend (26F, I’m going to call her “Jane”) and it has recently become a modern problem for me. So I’ve known Jane my entire life and we’ve always sort of had a crush on each other growing up. Jane broke up with her boyfriend around 2021 and reached out to me to vent about it. At that point I didn’t really look at her romantically and just considered her a family friend so I figured I’d help her out and introduce her to my friends because she lost a lot of her friend group after her breakup. Pretty soon after we all started hanging out my friends started telling me that she was interested in me so I started to think about our relationship differently. One thing led to another and a few weeks later we were hooking up regularly. The issue for me was Jane just got out of a breakup and wasn’t trying to commit to anything serious. That unfortunately wasn’t clear to me though and we continued dating for about a year before the whole friends with benefits dynamic became too much and we started arguing because I felt like I was just being led on. Honestly I should’ve ended it earlier but I deluded myself into thinking she just needed some time to get over her ex.

The relationship had also become very unlike friends with benefits. Lots of I love you, we had agreed to be exclusive from the start, we saw each other daily- basically the relationship was far from casual to me. Once it started getting very serious I feel like Jane pulled back a bit and I was like cool let’s end this. Jane didn’t want to do that either so it was a rough back and forth of struggling to find the right amount of love I should be giving this person. Ultimately, I couldn’t take the whole “should I stay or leave” of it all and said we should stop seeing each other. I was really crushed but we agreed to remain friends since our families are close and I’m good friends with her brothers.

Remaining friends was a bad idea. Throughout 2023 she would frequently reach out to me, send me funny videos and talk to me about general stuff. This made it very difficult to get over her. I eventually told her that staying in constant contact like this was making it hard for me and she understood so we fell out of communication. She started dating someone else and I would see her once a year at a Christmas party or something. That was great for me and I felt like I finally started to move on.

Now here’s where I really messed up. I’m close friends with Jane’s brother and have been my entire life. And after he graduated college and came back to town he wanted to hang out with me. This is around early 2024. I don’t have too many friends in town so I sort of join in his friend group, watch football on sundays and really just enjoyed hanging out with them. I felt some guilt in the back of my mind hanging out with Jane’s brother even though I wasn’t totally over her. And despite her brother certainly knowing that I dated his sister, him and I never discussed it once. I felt weird about that too but how do you just bring that up in conversation? I just wanted to leave past in the past and I was enjoying hanging with these new/old friends. And it was great. I really did get over her to the point I rarely thought of her or our relationship and when I did it rarely brought me down.

Flash forward to this year: we’re hanging over at my family friends house like we usually do and Jane comes over. It’s her parents house too so we’ve seen her a lot and she’s cool so we’re all hanging out. Totally cool, my feelings are there but I’m not really catching deeper feelings nor trying to rekindle anything. This is the most we had been consistently hanging out since we split and I thought it was finally great that we could all hang out and have a nice time together, having been family friends our entire life. For a few weeks it almost felt like everything was smoothed over and I was good.

Then she started hooking up with another one of my friends in this group. I know I have no right to be upset by this but seeing that develop while we’re hanging out really hurts me. I guess I’m not as over her as I thought. I don’t know what to do. I’m miserable every time I hang out in that group now but I really don’t have many friends around outside of them and I don’t want to lose all those friends just bc I’m upset over a girl I wasn’t ever really even with.

I feel really pathetic writing all this out. Reading it back I’m constantly facepalming but I just had to vent and get this all out to someone. I’m definitely going to distance myself from this friend group and I’m trying my best to fight the urge to confront my friend who is now with her like “hey you do know we used to date, right?” or confront her with “hey, do you really think coming around and hooking up with guys in front of me makes me feel good?” because confronting them like that is just really toxic behavior to me. I am unexpectedly very hurt though. It’s like I’m already sad I lost you and now you have to come around and mess up my friend group too. I don’t know. Any advice is appreciated I mainly just had to get this off my chest.

TLDR: I’m foolish and got in a terrible relationship with a family friend who I now see frequently in social settings.