Hollywood's Most Unlikely Couples!

Tuesday 5:20 PM, 02/03/2010
Hollywood's Most Unlikely Couples!

Sienna Miller and P. Diddy were spotted getting romantic during the summer of 2007. They are so totally different, we think this relationship was only ever about a bit of fun!

Michael Jackson and Brooke Shields dated for a short time while they were teenagers and stayed close friends for all of Michael's life. Brooke made a beautiful speech at Michael's funeral last year too.

Michael Jackson and Brooke Shields dated for a short time while they were teenagers and stayed close friends for all of Michael's life. Brooke made a beautiful speech at Michael's funeral last year too.
Tom Cruiseand Cher! Did you have any idea about this? We were pretty shocked when we read about this!

Tom Cruiseand Cher! Did you have any idea about this? We were pretty shocked when we read about this!

David Arquette and Alyssa Milano. Long before David fell in love with his wife Courteney Cox, he dated Alyssa. They were quite a hot red carpet couple in the 90's, but it didn't last.

David Arquette and Alyssa Milano. Long before David fell in love with his wife Courteney Cox, he dated Alyssa. They were quite a hot red carpet couple in the 90's, but it didn't last.

Justin Timberlake and Fergie dated very briefly when he was just 16 and Fergie was 23, but of course with that age difference, it wasn't meant to last!
Justin Timberlake and Fergie dated very briefly when he was just 16 and Fergie was 23, but of course with that age difference, it wasn't meant to last!
Lindsay Lohan and Aaron Carter. Aaron is a real casanova and has been with many stars. He is famous for dropping one girl and moving straight to another, just like he did with Hilary Duff who he dropped for Lindsay Lohan! It was pretty dramatic and its no wonder nothing good ever came of this coupling up!
Lindsay Lohan and Aaron Carter. Aaron is a real casanova and has been with many stars. He is famous for dropping one girl and moving straight to another, just like he did with Hilary Duff who he dropped for Lindsay Lohan! It was pretty dramatic and its no wonder nothing good ever came of this coupling up!
Brad Pitt and Christina Applegate dated long before the drama that was Jennifer Aniston and Angelina Jolie! It only lasted a short little while though and the two of them were seen partying a lot and many thought they made a fantastic couple. But it just wasn't meant to be!
Brad Pitt and Christina Applegate dated long before the drama that was Jennifer Aniston and Angelina Jolie! It only lasted a short little while though and the two of them were seen partying a lot and many thought they made a fantastic couple. But it just wasn't meant to be!
Joaquin Phoneix and Liv Tyler. We still think they make a cute couple! These two dated between 1995 and 1998 after meeting on a movie set. We kinda wish it had worked out!
Joaquin Phoneix and Liv Tyler. We still think they make a cute couple! These two dated between 1995 and 1998 after meeting on a movie set. We kinda wish it had worked out!
Who can keep track of all the guys Paris Hilton has dated, well Nick Carter was one of them! Well until Nick cheated with Jessica Simpson that is. Anyone remember that dramatic scandal?
Source: WENN.com

Who can keep track of all the guys Paris Hilton has dated, well Nick Carter was one of them! Well until Nick cheated with Jessica Simpson that is. Anyone remember that dramatic scandal?

You won't believe which Hollywood celebs have tried their luck at dating! They have made some of the most unlucky couples we have seen and we never would have imagined them together! Like Tom Cruise and Cher! Or maybe Sienna Miller and P. Diddy and how about Brooke Shields and Michael Jackson? Obviously these relationships didn't last very long, but its still fun to see which celebs have dated which isn't it! Take a look at our list and vote for your favourite unlikey couple!

Vote

Which couple did you like the best?


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Tags: Brad Pitt / Celebrity couples / Hot / Red Carpet
6 Comments
6(non member) 1
report abuse
02/03/2010 8:52 PM
nick is the best n he dont deserve paris!
Hely(non member) 2
report abuse
03/03/2010 3:23 PM
Why Liv and Joaquin not in poll?
MichaelJackson (Posh24 member) 3
report abuse
02/05/2010 1:57 PM
Michael Jackson and Brooke Shields were so great
together...
Astrid(non member) 4
report abuse
05/08/2010 2:09 AM
WOAH IM CALLING MOM
mar(non member) 5
report abuse
04/02/2012 5:49 AM
nick never dated jessica simpson and he never
cheated on paris actually she cheated on him with
chad michael murray
mariza(non member) 6
report abuse
04/02/2012 5:50 AM
posh you need to do more research your info is
just wrong
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