4 Joshua Burgin
Dated: Rachel
Pros: He has a vulnerability that makes him sweet. And he appreciates Rachel’s fashion advice. I mean, he must if he hired her as his personal shopper.
Cons: He’s recently divorced which means baggage. It’s Joshua who ultimately decides the relationship is moving too fast. (In real life, Tate Donovan and Jennifer Aniston were in the process of breaking up. How fun for them!)