She's a moron if she stays with that idiot. I can't imagine she's not out of his league. I don't know what her medical issues are (shockingly) but I imagine they're mental in nature in order to deal with the bromance between these two. It's like Matt Damon and Ben Affleck, only not as good looking, successful, intelligent or classy.
When they started arguing about whether the relationship was going to last, I wanted to turn around and say "Brosef here is right. One of these relationships isn't going to make it. Either you and Ashley are doomed, or the world's greatest, longest running bromance is about to end. Dude here is in love with you and hates Ashley. The two cannot coexist. There can only be one."
Whatever happened to going to sporting events and mostly watching the game while carrying on conversations in low voices so that everyone around you doesn't know your life story?