Chelsea Handler Plays Cupid For Jennifer Aniston

Jennifer Aniston

If the comedienne has her way, Jennifer Aniston won't be single for much longer.

Everybody needs that friend. You know, the one who takes you out for (strong) cocktails on the heels of a breakup and refuses to let you sit on the couch and mope. And who could use one of those pals more than Jennifer Aniston? She's had more than her share of disappointments - let's see, there was Josh Hopkins, and John Mayer, and Gerard Butler, and of course, the biggie: Brad Pitt. Need we go on?

Of course, it's not that Jen really needs new friends, per se. After all, her BFF status with Courtney Cox has been well-documented and she's got a full circle of trusted companions. In fact, Jen even rented two private planes over Thanksgiving to fly them all down to Cabo San Lucas in a Golden Girls-esque "Thank You For Being a Friend" move.

"Jen has more money than she will ever be able to spend in her lifetime, so she decided Thanksgiving was the perfect time to splurge on the most important people in her life," a source told Popeater.

One of the plane's passengers? No-holds-barred jokester Chelsea Handler, Jen's newest sidekick. And, according to Popeater, Chelsea thinks it's time for Jen to shake things up a bit and change her single status quo! Jennifer Aniston World's Most Eligible Single Gal?

"Many of Jen's closest friends were with her when Brad broke her heart and have discouraged her from spreading her wings too quickly for fear she will get hurt again," reports Popeater's source. "Chelsea is the opposite. She believes Jen is fabulous in her 40's and needs to paint the town red. No more sitting at home alone with her dogs. No more quiet dinners out with Courteney Cox and the girls."

And who better than bawdy Chelsea for Jen to hit up the town with? It's no secret that Chelsea's a huge fan of no-strings-attached flings, vodka, and just plain ol' having a good time. And if she can get Jen to date a member of 50 Cent's entourage, we'll really be impressed! Odd Couple Du Jour: Chelsea Handler and 50 Cent