Dallas Cowboys quarterback Tony Romo was dating Carrie Underwood before he took up with Jessica Simpson. Let's see - Carrie's career is thriving, and she's never confused tuna for chicken on TV. Our verdict: Downgrade. Sorry, Jess.
Reese Witherspoon went through a painful divorce with Ryan Phillippe, only to find happiness with Jake Gyllenhaal. We have no reason to believe Phillipe treated Reese badly, but we maintain any man foolish enough to let her slip away is no prize. Our verdict: upgrade.
We know Brad Pitt's wife has been called the most beautiful woman in the world by countless lists, and the couple have a million children together. We're not going to lie, though: we're a little sick of The Brangelina - and we picked Jennifer Aniston as PopEater's 2008 Person of the Year. Our verdict: Downgrade. Yeah, we said it.
Ryan Reynolds was once engaged to singer Alanis Morissette, but he married Scarlett Johansson. Scarlett is no doubt one of the most beautiful women in the world - but have you heard her sing? Still... she's just too pretty. Our verdict? Upgrade.
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Though Nicole Kidman's marriage to Keith Urban is not without its apparent challenges, they have a beautiful baby girl together - and Keith lacks Tom Cruise's over-the-top crazy gene. The marriage simply comes off as much happier than Kidman's first. Our verdict? Upgrade.
Justin Timberlake went through blondes Britney Spears and Cameron Diaz before landing his current brunette flame Jessica Biel. We admit, he and Jess seem like a strong match.
Our verdict? Slight upgrade from Cam, large upgrade from Brit.
Okay, we're going to be honest here: we never got over the couch-jumping, semi-brainwashy shenanigans that marked the beginning of Katie Holmes' relationship with Tom Cruise. It was weird. But her ex-boyfriend Chris Klein was SUCH A JERK that we are forced to call this an obligatory upgrade.
Balthazar Getty was theoretically separated from his wife and the mother of his children the day he was photographed kissing Sienna Miller. We're suspicious, yet we're glad she's moved on from that nanny-loving louse Jude Law. Our verdict: Sliiiiight upgrade.
Rachel Hunter was married to rocker Rod Stewart - 24 years her senior - from 1990 to 2006. She is currently engaged to ice-hockey player, Jarret Stoll - 13 years her junior. Do we really have to say it? Our verdict: Big upgrade.
'Girl Next Door' Kendra Wilkinson is now engaged to Philadelphia Eagles wide receiver Hank Baskett, after living in the Playboy mansion as Hugh Hefner's third girlfriend. As far as we know, Baskett has only one girlfriend, and he was born in the same century as Wilkinson, so... Our verdict: upgrade.