Howdy y’all. So I’m only a junior in highschool, and over the summer I had a rocky break up with my now ex who is going into freshman year of college. He texts me every so often and we chat about how or day was or whatever, and then somehow he always turns it into a sob fest about how lonely he is and how his life won’t be the same and he is paranoid all the time. I have no idea what to do anymore because anything I say is never good enough! I’ve tried several different approaches and nothing has made him leave me alone or stop bringing up the past. I thought highschool relationships were bad but I didn’t think a boy going into college would get this hung up...

Hi, hope this will help!
You don't need that kind of negativity in your life, if he bothers you to much and what you say is "never good enough" for him then block him or stop answering.

Sounds like hes remembering all the good bits making himself feel shit about where he is at and nothing u do can live up to his remembered "perfection". Just be honest blunt with him, tell him you dont want to move on and stop talking about the past and if he dosen't listen block the clingy fucker. You do you, his problems arent yours to fix anymore.

Source- a very jelous and controlling ex, after we broke up he kept wanting to make things the same as how they were before, but i was never "good enough".

oops i made a typo >n< the 2nd sentence is supposed to say:

*Just be honest and blunt with him, tell him you want to move on and stop talking about the past and if he doesn't listen, then block the clingy fucker.*