Fucking Finally! Took me three times to break up with him! I think he’ll leave me alone this time! I feel like a complete asshole though! He’s an absolute mess because of it. I know its emotional black mail, but I still feel responsible for his agony! What do I do? Do I stay friends with him?

Fuck no. For your sake and for his, no contact for a good long while. None.

When it’s messy and one-sided, the person doing the breaking needs to treat that shit like an execution. Don’t let it be slow and painful. You gotta be strong enough to make it clean, fast, and permanent.

There’s no need to be mean about it. You don’t even have to be cold. Just be firm and unwavering in establishing the new boundaries, and don’t for one second put up with any emotional blackmail.

He is responsible for his own emotional state, and you are only responsible for his agony to the extent that you keep prolonging it by giving him false hope. It’s over. Don’t even stick around to see which way the body falls. Just walk away and don’t look back.