Yeah, what's gross here is that Jay starts out being really creepy, talking about seeing off "my girl" going off on her cute "adventure" and suggesting he'll come out to see her as if they're still going out. So her firmly telling him that they really did break up and he's not just going to ignore it and treat her like his girlfriend until she gives in makes sense.

But then she reveals that she broke up with him for terrible reasons that are wrong and make her shallow and horrible--and sound like a set up for him to Prove Her Wrong. Which is what makes it into a bit of a creepy sexist fantasy. She's a horrible person, but she should be a horrible person who wants him. Suddenly it's just all that her being a jerk and he's just being nice and supportive despite the fact that she doesn't deserve it.