I understand the apples to grapes comparison you're trying to make, but the puzzle pieces don't quite fit for a number of reasons. He was the one to dump her, because the relationship was taking up too much of his time/energy, and he cut off their friendship because she didn't respect his boundaries.

He said this made him reevaluate her as a person. I'm sure there's more to the story but this is basically what happened (confirmed by other sources). And this relationship damaged his confidence and made him very jaded about love.

I know the good ones can't be ruined and that this heartbreak only brought out qualities in him that were already there, but she doesn't sound that great. Somehow he thought I was too much work and not as loving or giving as she was. And he never said he was unhappy with anything I did. How does that make sense?