Want to reconnect with an old "boyfriend" I feel he is still bitter and I am being selfish, what to do?

This guy and I met in August of 2025 during a festival. He was interested in me but didn't say anything until his friends and my friends set us up without my knowledge. For later context I suffer from OCD and back then, in August, I didn't struggle with my mental health the way I do now so I was naturally more social and optimistic in my day to day life. The first few weeks of us getting to know each other felt great, we connected with each other and I felt really happy. I wasn't having doubts yet but soon i got into big trouble with my parents that shattered my family's dynamic (the guy has nothing to do with it), soon after that, a school friend of mine that was very close with some of my other friends sadly passed away. This series of tragedies are what I believe kickstarted my mental health getting bad again. My now ex-best friend also had a lot to say about my relationship with this guy, we both knew he was a little awkward and didn't have a lot of hobbies, he kinda just did very basic human tasks everyday and talked to me; that was his whole routine, and although i liked him very much, to me it was getting annoying. My exBSF constantly mocked him and judged me for engaging with him romantically and i began getting doubtful due to the constant judgement and my OCD. It got too overwhelming and i wanted my friend's approval so bad I somehow convinced myself I wasn't interested in him anymore, so I ended it with him (this was late November aroundish for imagery).

For weeks i pined and regretted what i did, there were times of relief when i had time for myself to engage with my hobbies but i missed him a lot. Then, finally after three weeks i stopped him in the middle of school and asked to talk to him , saying how much i missed him and wanted to try again and he agreed, he looked very happy when we restarted but i started getting doubtful again due to the thought of what my friend would say. I suffered everyday knowing that she was judging me and saw me as inferior for pursuing a romantic relationship with him again or any guy for that matter and this made my mental health much worse again (yes, this will keep happening). I was and still am very afraid of judgement and I don't remember anything from this winter due to a depressive episode so i cant remember my thought process when i ended it with him again in mid January, the look on his face being let down a second time shatters my heart every time i imagine it.

It was easy for me to imagine him as the bad guy or me being too good for him because it was cope but in all honesty, I was just depressed and anxious and thought he was the problem, making me take it out on him and blame him for why I was so sad all the time, i cringe and hate myself for this. Ending my friendship with my bestfriend whom i loved most in the world was an eye opening experience. My fear or judgment has significantly decreased since and Ive been thinking of him again due to something i saw while at lunch. In the cafeteria, my friend group and his sit very close to each other and his back is ussualy turned to me which embarassingly enough makes it very easy to stare at him and wonder. One time as I was staring, his shirt lifted and i saw him wearing a belt I gave him for christmas. This guy is a very petty and sour individual when he doesnt like people, so i dont understand why he wouldn't be petty about the belt. I was always aware he wasn't over me and I think he knows I'm not over him either but the belt (which has a lot of symbolism that I don't want to get into right now) shocked me. If we are both not over each other i don't understand why we're dancing around this when we both just want each other again (allegedly). I believe he is scared of me leaving again and i am too, I hate my ROCD and my people-pleasing tendencies that makes me act this way and ruins my relationships with the people i love most.

This is what makes me wonder, This is really exhausting to think about especially since its been months but something is up and I don't want to suffer because of this anymore. I should say that i am not asking for reassurance but guidance of what to do about this situation, if i should completely leave it be and suffer or do something about it and if i should, then what and how should i approach it?