Throwback!See 9 Celebrity Friend Duos Who’ve Dated the Same Person

Jennifer Aniston and Courteney Cox both dated…

…Adam Duritz!

Jen and Adam were linked in 1995 and Courteney dated The Counting Crows frontman in 1997 after she appeared in one of his band's music videos.

Kate Hudson and Cameron Diaz both dated…

…Alex Rodriguez!

Kate briefly dated the pro baseball player in 2009 while Cameron was in a long-term relationship with Alex from spring 2010 until fall 2011.

Ben Affleck and Brad Pitt both dated…

…Gwyneth Paltrow!

The actress and Brad dated from 1994 to 1997 and were briefly engaged. Gwyn and Ben later dated from 1997 until 2000.

Ryan Gosling and Matthew McConaughey both dated…

…Sandra Bullock!

The actress dated Matthew from 1997 until 1998. Sandra and Ryan later dated after costarring in the 2002 movie Murder By Numbers.

Johnny Depp and Matt Damon both dated…

…Winona Ryder!

The actress and Johnny were engaged for three years from 1990 until 1993. Matt and Winona dated from 1998 until 2000.

Jennifer Lopez and Cameron Diaz both dated…

…Sean Combs!

J.Lo and Diddy famously dated from 1998 until 2001. Cameron was casually linked to the rapper several times between 2008 and 2012.

Owen Wilson and Lance Armstrong both dated…

…Sheryl Crow!

Owen and Sheryl dated in the 90s. Lance and the "Soak Up the Sun" singer began dating in 2003 and announced their engagement in September 2005. Sadly, the two later split in February 2006.

Drew Barrymore and Kristen Wiig both dated…

…Fabrizio Moretti!

Drew and The Strokes drummer dated from 2002 until 2007. Then, Kristen and Fabrizio were an item from 2011 to 2013.

Matthew Rhys and Balthazar Getty both dated…

…Sienna Miller!

Sienna and Balthazar briefly dated in 2008. Sienna and Matthew were in a relationship that same year.

Enter here to win $1000 cash!