Odd Celebrity Couples - Can You Believe These Celebrities Dated?

It's no surprise celebrities date one another, they work together, go to the same places, have the same friends, and understand each other and the "business." However, there are some celebrity couples that the public just doesn't understand. Some couples are so mismatched that you wonder what the heck he or she was thinking? Here is a list of some of the oddest celebrity couples. They may not have lasted long but anyone could have told them that it was a mistake from the beginning.

Drew Barrymore has been in the business since she was a child, maybe that's why she has dated so many movie stars. However, some of her matches have been very questionable. Here are just a few of the head scratching men she dated in her past.

Drew Barrymore and Corey Feldman: Dated briefly in 1989

Drew Barrymore and David Arquette: Dated briefly in 1991

Drew Barrymore and Tom Green: Married briefly in 2001. Divorced in 2002.

These two dated well before either one truly hit the big time. The couple isn't so much odd, but just a surprise. I had no idea they were a couple at any time.

These two were together for SEVEN years! Wow.... that's long than most celebrity marriages last!

AKA: Puff Daddy AKA: Sean Combs AKA: P Diddy

Whatever name he is going by, thee is something women find attractive about Mr. Combs. P. Diddy has dated some beautiful women but you have think what were they thinking. IT'S P. DIDDY, do you really think someone who calls himself P.DIDDY or Puff Daddy is looking to settle down?

Lil Kim and Sean Combs: Dated 1997 - 1998

Jennifer Lopez and Sean Combs: Dated 1999 - 2001. Everything was going well until the shooting! WHAT?!?! Lopez was actually arrested and charged with a possession of a weapon, when a gun went off in the car Lopez and Combs arrived to a club in. Three people were shot and wounded.

Sienna Miller and Sean Combs: Dated in 2007

These two dated in 1989, long enough for Ted Danson to stupidly appear in black face at the Friar's Club by the encouraging of his current girlfriend Whoopi Goldberg. Danson got a lot of flack for his performance, which Goldberg said she encouraged him to do and admitted she wrote his racial filled comedy act. It was a sad moment for Danson. Not long after his stupidity the two broke up.

Dated from 1983-1984, well... it depends on who you ask. Shields has always denied that the two dated and has always insisted they were just good friends who understood each other because they were both child entertainers. However, Jackson had stated several times that the two did indeed date in interviews and in an autobiography.

Dated from 2004-2006

This mismatched couple makes you wonder what a seemingly intelligent person like Connolly was thinking dating a Hilton just months after she had her marriage annulled in 2004. The two broke up when Hilton suspected Connolly of cheating on her.

Tom Cruise and Cher: in the mid 1980s. Cher counts Cruise as one of her top lovers. Cher admits she was crazy about him but Cruise was still getting used to his super stardom.

Val Kilmer and Cher: Dated in the mid 1980s too

Richie Sambora and Cher: 1989-1990

Robin Givens and Pitt: Dated in 1988 for six months, but Mike Tyson still liked her, so let's just say Pitt backed off.

Christina Applegate and Pitt: Dated when she was 18 and Pitt was 25. Their first outing was at the MTV Music Awards, she arrived with him but left with someone else. Poor Christina.

Juliette Lewis and Pitt: Dated 1989-1993 Began dating when Lewis was 16 and Pitt was 26. What the heck????? Pitt certainly liked his women younger than him, and still does Angelina Jolie is eleven years younger than Pitt.

Heather Locklear and Scott Baio: Dated early 1980s. Baio claims she was the "Greatest chick, but he just ruined it"

Heather Locklear and Tom Cruise: Dated in the 1980s. Locklear claims it was just one date. But the two were caught multiple times together as a couple.

Heather Locklear and David Spade: Dated in 2006 when Locklear needed a friend.

Hillary Duff and Aaron Carter: Dated from 2000 - 2003 when they were both teens. With the recent news that Duff broke up with her husband, Carter reappeared in the tabloids stating that Duff was the love of his life.

Lindsay Lohan and Aaron Carter: Dated from 2002-2003. Carter is quoted as saying he got bored with Duff at the time and moved onto to Lohan.

Brooke Hogan and Aaron Carter: Dated in 2007

Adam Duritz and Aniston: Dated briefly in 1995. Wow talk about an odd couple

Tate Donovan and Aniston: Dated from 1995-1998. The two were even engaged for a few months before calling it off. Donovan appeared on Aniston's tv sitcom as her love interest when they were engaged.

Paul Rudd and Aniston: Dated briefly in 1998 after starring together in the movie "Object of My Affection." Okay I must admit this was a kind of a cute couple!!!

Robe Low and Ryder: Dated from 1986-1988

Christian Slater and Ryder: Dated in 1988. The two began dating while filming the movie "Heathers." In an interview in 2007, Slater states that Ryder was the girl of his dreams.

Johnny Depp and Ryder: Dated from 1989 - 1993. The two were engaged after dating for only a few months but the marriage never happened.

Matt Damon and Ryder: Dated from 1997 - 2000 after being introduced by Ben Affleck

Jimmy Fallon and Ryder: Dated in 2000

Val Kilmer and Ryder: Dated in 2006