Who Should Date Jennifer Aniston?

They once laughed at the very notion of Demi Moore and Ashton Kutcher, and maybe they still do, but at least they're married. It's Hollywood hip for actresses to take up with younger men, so Jen may want to go "Brokeback" with Jake Gyllenhaal. "What a great transition from Brad, and a nice change from Vince Vaughn, who's a doll, but he's not exactly stepping up to the plate," said April Masini, online advice columnist and author of "Date Out of Your League."

Jake's Status: 25, single, once linked to Kirsten Dunst Career Highlight: Oscar nomination for "Brokeback Mountain."
(AP Photo/Chris Pizzello)