There's no question why Rory Gilmore wanted to date Jess Mariano on Gilmore Girls.
He's a total heartthrob who shared her taste in books and music.
And did I mention he's a total heartthrob?
But unfortunately, Jess wasn't without his flaws.
He didn't always call Rory to make plans, wasn't exactly emotionally there for her in ways she needed, and he kind of left Stars Hollow for good without saying bye.
