From PEOPLE Magazine Click to enlarge
BATMAN + CATWOMAN = WILD KINGDOM
George Clooney & Halle Berry
Holy golden couple! PEOPLE's onetime Sexiest Man Alive and Most Beautiful Woman share the same sentiment about marriage: never again.

HE'S A TWIN
SHE'S A TWIN

Olympic gold medalist Paul Hamm & Ashley Olsen
They're both petite undergrads who juggle careers and school. (They could even match up sibs Morgan and Mary-Kate for a double date.)

IVY LEAGUE SMARTS
Jake Gyllenhaal & Kate Bosworth
He was a Columbia philosophy major. She got into Princeton.

BOTH HAVE FAMOUS OLDER SISTERS
Jack Osbourne & Ashlee Simpson
They've endured a spotlight-grabbing big sis and share firsthand expertise in reality TV.

A CANADIAN THING
Sandra Oh & Jim Carrey
Two quirky, creative, very funny north-of-the-border imports who beat the showbiz odds.

WHO SHOULD JEN DATE?

Orlando Bloom
If she wants a younger guy, why not try one dubbed "the next Brad Pitt"?

Chris Heinz
The political heir wouldn't be interested in her money—and she's big on the Dems.

Steven Tyler
She's had a longtime crush on the rocker—her designated "love freebie" during marriage to Brad Pitt. He also recently separated from Teresa, his second wife of 17 years.