I’ve been talking to this guy for a while now and we’ve been on and off. We both have feelings for each other and want to talk to each other constantly. I told him how I missed him and we both said we were going to try and work it out but then he says, “it doesn’t feel like it’ll work.”

I have no idea what to say back to him. I really like him but I’m such an overthinker.. help

UPDATE:

So we started talking again but he won’t give me a definite answer if he wants to keep going or not. Should I even keep on trying to make it work or let go of him?