Matthew McConaughey

Who Should Date Jennifer Aniston?

Jen's successful, fabulously wealthy and beautiful. Perhaps that's enough to scare off any man alive. … Except Matthew McConaughey, a match that would pair People's "Sexiest Man Alive" with GQ's "Woman of the Year." "Despite their success, they're both laid-back, bohemian types who live in the moment," said Jill Spiegel, author of "The Flirtologist's Guide to Dating."

Matthew's Status: Single, 36, dating Penelope Cruz
Career Highlight: Went from "Dazed and Confused" to Kate Hudson's guy in "How to Lose a Guy in Ten Days."
(AP Photo/Jeff Christensen)