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37 Stars You'll Be Shocked Used To Be Couples

AUGUST 12, 2015  —  By Jason Lopez

37 Stars You'll Be Shocked Used To Be Couples

1. Ryan Gosling and Sandra Bullock - 2002

1. Ryan Gosling and Sandra Bullock - 2002

amusedmedia

2. George Clooney and Renee Zellweger - 2001

2. George Clooney and Renee Zellweger - 2001

wellnest

3. Brad Pitt and Robin Givens - 1988

3. Brad Pitt and Robin Givens - 1988

TODAY

4. Winona Ryder and Matt Damon - 1997 to 2000

4. Winona Ryder and Matt Damon - 1997 to 2000

Pinterest

5. Heath Ledger and Heather Graham - 2000 to 2001

5. Heath Ledger and Heather Graham - 2000 to 2001

Stars

6. Courteney Cox and Michael Keaton - 1989 to 1995

6. Courteney Cox and Michael Keaton - 1989 to 1995

Stars

7. Winona Ryder and Jimmy Fallon - 2002

7. Winona Ryder and Jimmy Fallon - 2002

Pinterest

8. Cameron Diaz and Matt Dillon - 1995 to 1998

8. Cameron Diaz and Matt Dillon - 1995 to 1998

wellnest

9. Cher and Tom Cruise - 1980s

9. Cher and Tom Cruise - 1980s

Pinterest

10. Justin Timberlake and Fergie - 1996

10. Justin Timberlake and Fergie - 1996

Bet

They had a fling when Fergie was 23 and Justin was only 16. Justin obviously has no hard feelings, because they're pictured performing together in 2013.

11. Johnny Depp and Ellen Barkin - 1994

11. Johnny Depp and Ellen Barkin - 1994

imgbuddy

12. Ashton Kutcher and Brittany Murphy - 2003

12. Ashton Kutcher and Brittany Murphy - 2003

wellnest

13. Leonardo DiCaprio and Naomi Campbell - 1995

13. Leonardo DiCaprio and Naomi Campbell - 1995

stylista

14. Moby and Natalie Portman - 2001

14. Moby and Natalie Portman - 2001

Pinterest

15. Ben Affleck and J-Lo - 2002 to 2004

15. Ben Affleck and J-Lo - 2002 to 2004

eju!

16. Kiefer Sutherland and Julia Roberts - 1990 to 1991

16. Kiefer Sutherland and Julia Roberts - 1990 to 1991

wellnest

17. Drew Barrymore and Luke Wilson - 1996 to 1999

17. Drew Barrymore and Luke Wilson - 1996 to 1999

Pinterest

18. Jennifer Grey and Matthew Broderick - 1987 to 1988

18. Jennifer Grey and Matthew Broderick - 1987 to 1988

Stars

19. Sheryl Crow and Owen Wilson - 1999

19. Sheryl Crow and Owen Wilson - 1999

wellnest

20. Macauley Culkin and Mila Kunis - 2002 to 2011

20. Macauley Culkin and Mila Kunis - 2002 to 2011

Stars

21. Johnny Lee Miller and Angelina Jolie - 1996 to 1999

21. Johnny Lee Miller and Angelina Jolie - 1996 to 1999

Pinterest

22. Jennifer Aniston and Vince Vaughn - 2005 to 2006

22. Jennifer Aniston and Vince Vaughn - 2005 to 2006

Digital Spy

23. Andre Agassi and Brooke Shields - 1993 to 1999

23. Andre Agassi and Brooke Shields - 1993 to 1999

Pinterest

24. Emma Stone and Kieran Culkin - 2009 to 2010

24. Emma Stone and Kieran Culkin - 2009 to 2010

wellnest

25. Sandra Bullock and Matthew McConnaughy - late 1990s

25. Sandra Bullock and Matthew McConnaughy - late 1990s

offbeat

26. Britney Spears and Colin Farrell - 2003

26. Britney Spears and Colin Farrell - 2003

imgbuddy

27. Jack Nicholson and Lara Flynn Boyle - 1999 to 2006

27. Jack Nicholson and Lara Flynn Boyle - 1999 to 2006

wellnest

28. Edward Norton and Salma Hayek - 1999 to 2003

28. Edward Norton and Salma Hayek - 1999 to 2003

Pinterest

29. Josh Groban and January Jones - 2003 to 2006

29. Josh Groban and January Jones - 2003 to 2006

Stars

30. Lenny Kravitz and Nicole Kidman - 2003

30. Lenny Kravitz and Nicole Kidman - 2003

US magazine

31. Helen Hunt and Matthew Broderick - 1987

31. Helen Hunt and Matthew Broderick - 1987

wellnest

32. Orlando Bloom and Kate Bosworth - 2003 to 2006

32. Orlando Bloom and Kate Bosworth - 2003 to 2006

Pinterest

33. Ryan Reynolds and Alanis Morissette - 2002 to 07

33. Ryan Reynolds and Alanis Morissette - 2002 to 07

Stars

34. Matthew Morrison and Kristen Bell - dated as undergrads

34. Matthew Morrison and Kristen Bell - dated as undergrads

Stars

35. Rhys Ifans and Sienna Miller - 2007 to 2008

35. Rhys Ifans and Sienna Miller - 2007 to 2008

Stars

36. Emma Thompson and Hugh Laurie - 1979

36. Emma Thompson and Hugh Laurie - 1979

NUR KZ

They had a fling while undergraduates together in Cambridge, some time around 1979.