Most Awkward Celebrity Couples

November 11, 2012 By:
Most Awkward Celebrity Couples

Tyra Banks and Seal? Fergie and Justin Timberlake? Tom Cruise and Sofia Vergara!

These are the most random couples, the WTF couples, the pairings that make you say "He dated her?" and the couples that I bet you didn't know dated. Basically, these are some of the most surprising celebrity pairings.

Tom Cruise and Sofia Vergara: I can barely wrap my head around this one, but Tom Cruise dated Sofia Vergara in 2005, long before she was a household name (and probably back when Tom thought he could brainwash her with Scientology into becoming his wife!) They were introduced by mutual friend Will Smith, but eventually Sofia ended things because of Tom’s obsession with the “S” word. And yes, “S” word always means “Scientology.”

Jay Z and Rosario Dawson: I just assumed Jay-Z and Beyonce have been together their entire lives, but believe it or not, Jay-Z had a love-life before Beyonce and was actually linked to actress Rosario Dawson! Shortly after they broke up he met Bey and well, we know how that one turned out!

Tyra Banks and Seal: Seal must have some kind of secret love weapon, because before he married supermodel Heidi Klum he dated supermodel Tyra Banks. They dated for about 6 months in 1996 but broke up probably because that’s too much perfect bone structure in one couple!

Fergie and Justin Timberlake: Woa! Cougar Alert! Back when Fergie was 23 (and went by the name Stacy) she dated a then 16-year-old Justin Timberlake. Fergie had yet to join the Black Eyed Peas and Justin was just at the beginning of his N’Sync fame. They eventually fizzled out because JT was a CHILD!

Brad Pitt and Christina Applegate: Thanks to Christina Applegate’s breakout role as Kelly HOT Bundy on “Married With Children” she caught the eye of a then not-famous Brad Pitt in 1988. They dated for about a year but Christina dumped him at the 1989 MTV Music Awards. This story is mostly surprising because I can’t even imagine Brad FREAKING Pitt going anywhere near the MTV Music Awards.

George Clooney and Lucy Liu: Mostly because George Clooney has lately been shacking up with women whose careers aren’t nearly as exciting as his, George briefly dated actress Lucy Liu in 2000. George with a respectable actress!? NO! They were also caught making out in the back of a limo in NYC in 2005.

Tiger Woods and LeAnn Rimes: LeAnn Rimes and Tiger Woods reportedly dated back in 2002, which oddly makes a lot of sense because the two went on to have highly public cheating scandals.

Johnny Depp and Jennifer Grey: Long before Vanessa Paradis, Kate Moss, or even Winona Ryder, Johnny Depp was ENGAGED to “Dirty Dancing” actress Jennifer Grey. Obviously they didn’t get hitched, and honestly Jennifer seems too tame for Johnny?

Amanda Bynes and Seth MacFarlane: Before Amanda Bynes was the whacked out car-crashing starlet she is now, she dated a then 34-year-old Seth MacFarlane when she was only 22. Clearly Seth likes ‘em really young, he’s currently dating “Game of Thrones” star, Emilia Clarke.

Josh Groban and Katy Perry: Josh Groban and Katy Perry dated briefly in 2009, though they both managed to keep it pretty hush-hush. I’m mostly shocked how Josh Groban snagged both her AND January Jones and did you know that Katy Perry once dated Johnny Lewis, the “Sons Of Anarchy” actor that just killed his landlady and died earlier this week? Weird.

Diane Keaton and Keanu Reeves: Despite their 20-year age gap, the cougarific Diane Keaton dated Keanu Reeves after playing lovers in “Something’s Gotta Give.” Both have famously never married, so 2nd times the charm?