Bad Boys Do It Better OK, maybe in this case Logan and Jess are both on the wilder end of the spectrum, given that Rory’s only other significant ex is the goodhearted and totally well-intended Dean Forester (Jared Padalecki).
But Jess has never denied his rebellious behavior, or tried to hide behind the fact that he’s a bad boy at heart.
Judgments aside, Logan and Rory both cheated on those they were committed to in order to be with each other because it felt right, but such a relationship is probably unsustainable.
Nonetheless, Rory didn’t need to fly back to London to be with Logan — who, as it turned out, didn’t have intentions of leaving Odette to be with her — when Jess was seemingly still pining for her all along.
After all, the man was engaged to another woman — French heiress Odette — while simultaneously dating Rory, giving viewers reason to believe that he would leave his fiancée to finally settle down with the aspiring journalist.
This also meant having the guys themselves chime in.
Jared Padalecki (Dean) refused to pick himself but made a choice; Matt Czuchry (Logan) was the most diplomatic of all; and Milo Ventimiglia (Jess) had the kind of complicated answer you'd expect from a dude who never played by the rules in Stars Hollow.
For those who don't know, there are three teams backing past boyfriends as strong contenders — Team Jess, Team Dean, and Team Logan.
All claim that Rory Gilmore's heart has always belonged to one man.