Last year I dated on and of with this kid and he kept saying he liked me then I ended it because he never really acted like a boyfriend to me. Then this year he told me he liked me again so I gave him another try he stepped up his game but I never really felt it going anywhere so I started to like another guy and ended up dumping him again. I feel really bad but we still text each other now I'm starting to like him again and am afraid if I say anything about it or like him more he'll take it as like a joke because of before. Is it hopeless?

Yes it is hopeless. Leave him alone apparently he's not on your level and the more you talk to him the more you bring up memories and the more you will be at a stand still with everything, its clear that he's not on his game now, I mean in the future if you all meet again and he's better and more mature for you then try to pursue more but now live your life and be with someone that can relate to your feelings.