[PSY]

Ooh, I didn't realize that you broke up over the summer. So you tried to work things out last year, and couldn't, so you broke up. You got back together, things were okay for a while... but now you're back where you started. I think that's a pretty clear sign that it's not something you CAN work out.

And yeah, it's going to suck... for both of you. You've been together for a long time, and the routine will be gone. He's going to struggle with not having anyone to talk to, and you're going to struggle with whether or not you did the right thing by leaving him... but remember that you're not doing him (or yourself) any favors by staying with him under false pretenses.

Maybe, given time, you'll be able to rekindle a friendship... but after the two of you break up, it'd probably be best if you limited your contact with him. You know how messy (and painful) the "let's be friends" situation can be... it won't help him gain closure and move on, and it'll only postpone his search for new friends (and possibly girlfriends), if he feels like he still has a chance with you, and can count on you to be there for him 24/7.