It sounds like you are more worried about him than you.
Like you said, he enjoys girls pining. Breaking up, getting back, then breaking up again. Let him be and figure that one out without you.
Good luck to him. Later...
You don't deserve this. Your past friendship is one one thing, your relationship after is another.
The reality, and an unfortunate thing is that sometimes we don't want the same things. Sometimes it takes a breakup to slap us in the face to help us realize that.
Don't worry. You will be fine and better for someone who is better suited.
Don't be concerned about his list. You're not crazy. He his.
Do you want someone with a list anyway?
That may be a good thing to talk to your therapist about. Why you went from friends to partners. Maybe a friend is all he ever wanted. Maybe he enjoyed the benefits without ever really wanted to commit.

