Best thing that ever happened to himRemember those pictures of her grabbing his crotchsicle? There's only one reason a girl that hot would stay with a nowhere guy like that: he's got the magic missile. Like John and Jen, it's the only thing that makes sense - he rocks her world.
So why did they break up in the first place? Probably because of ego: she's an upwardly mobile sex kitten and his career peaked with taking Tori Spelling's virginity. Yeah, I know. How do you top that? (Without being arrested or killing puppies.)
Will these two make it? Probably not, if he can't learn to live in her shadow, walking two steps behind her a la Nick Cannon. He really doesn't look the type to be able to eat that for too long, though. He'll probably end up schtupping the housekeeper or something and that'll be the end of it.