ArtsAutosBooksBusinessEducationEntertainmentFamilyFashionFoodGamesGenderHealthHolidaysHomeHubPagesPersonal FinancePetsPoliticsReligionSportsTechnologyTravel
  • »
  • Entertainment and Media»
  • Celebrities

Odd Celebrity Couples - Can You Believe These Celebrities Dated?

Updated on July 31, 2014

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.

Feldman and Barrymore
Feldman and Barrymore
Arquette and Barrymore
Arquette and Barrymore
Green and Barrymore
Green and Barrymore

Serial Mismatch Dater: Drew Barrymore

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.


Parker and Downey Jr.
Parker and Downey Jr.

Sarah Jessica Parker and Robert Downey Jr.

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!

Combs and Lil Kim
Combs and Lil Kim
Combs and Lopez
Combs and Lopez
Combs and Miller
Combs and Miller

Sean Combs and the Women Silly Enough to Date Him

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





Danson and Goldberg
Danson and Goldberg

Ted Danson and Whoopi Goldberg

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.

Shields and Jackson
Shields and Jackson

Brooke Shields and Michael Jackson

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.

Hilton and Connolly
Hilton and Connolly

Nicky Hilton and Kevin Connolly

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.

Cruise and Cher
Cruise and Cher
Kilmer and Cher
Kilmer and Cher
Sambora and Cher
Sambora and Cher

Cher and her Boy Toys

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





Pitt and Givens
Pitt and Givens
Pitt and Applegate
Pitt and Applegate
Lewis and Pitt
Lewis and Pitt

Brad Pitt and the Ladies He Dated Before He Was A Star

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.

Locklear and Baio
Locklear and Baio
Locklear and Cruise
Locklear and Cruise
Spade and Locklear
Spade and Locklear

Heather Locklear and Her Odd Choices of Companions

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.






Duff and Carter
Duff and Carter
Carter and Lohan
Carter and Lohan
Carter and Hogan
Carter and Hogan

Aaron Carter Who??

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

Aniston and Duritz
Aniston and Duritz
Aniston and Donovan
Aniston and Donovan
Rudd and Aniston
Rudd and Aniston

Jennifer Aniston: Before Brad Pitt

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!!!



Lowe and Ryder
Lowe and Ryder
Ryder and Slater
Ryder and Slater
Depp and Ryder
Depp and Ryder
Damon and Ryder
Damon and Ryder
Ryder and Fallon
Ryder and Fallon
Ryder and Kilmer
Ryder and Kilmer

Winono Ryder Prior To Becoming a Crazy Shoplifter

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

Comments

    0 of 8192 characters used
    Post Comment

    • TheShadowSpecter profile image

      Jason B Truth 9 months ago from United States of America

      It's amazing how Drew Barrymore doesn't look much different now in her forties than she did when she was a teenager. Of course, she was blessed twice in life in terms of how the aging process treated her. The first time when she was a teenager. That is, in the picture in the above article, she is 14 years old and yet she could have gotten into any casino to play the slot machines without even needing to show fake I.D., even if she had not been a celebrity. The second time when she got past forty. That is, now that she is in her forties, she still has that same youthful glow that she did when she was in her teens and early twenties. It is no wonder that a lot of people still think of her as this vibrant kid instead of as a middle-aged woman. Good for her!

    • LailaK profile image

      LailaK 3 years ago from Atlanta, Georgia

      Interesting list! Voted up :)