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17 Celeb Couples That'll Make You Say, "Wait, They Dated?!"

Love. It can happen to ANYONE.

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1. Justin Timberlake and Fergie:

The two went out in 1997 when Justin was just 16 and Fergie was 23.
Frank Micelotta / Getty Images

The two went out in 1997 when Justin was just 16 and Fergie was 23.

2. Josh Groban and January Jones:

They dated for two and half years! Do you think he ever sang to her?
David Livingston / Getty Images

They dated for two and half years! Do you think he ever sang to her?

3. Evan Rachel Wood and Marilyn Manson:

They started dating in 2006 when Evan was just a teen. In 2010 they got engaged but split in 2011.
Scott Wintrow / Getty Images

They started dating in 2006 when Evan was just a teen. In 2010 they got engaged but split in 2011.

4. Avril Lavigne and Brody Jenner:

They dated! For two years! He wasn't a sk8r boi so she said c u l8r boi.
Ilya S. Savenok / Getty Images

They dated! For two years! He wasn't a sk8r boi so she said c u l8r boi.

5. Ryan Reynolds and Alanis Morissette:

They almost got married in 2004 after dating for several years. Also, did you forget he literally did marry Scarlett Johansson? Because that also happened.
Frazer Harrison / Getty Images

They almost got married in 2004 after dating for several years. Also, did you forget he literally did marry Scarlett Johansson? Because that also happened.

6. Ryan Gosling and Sandra Bullock:

They dated in 2002 despite their 16-year age difference. Get it, Sandy.
Francois Guillot / AFP / Getty Images

They dated in 2002 despite their 16-year age difference. Get it, Sandy.

7. Milo Ventimiglia and Alexis Bledel:

They secretly dated for four years in the early aughts. Rory and Jess IRL 4eva.
Matthew Peyton / Getty Images

They secretly dated for four years in the early aughts. Rory and Jess IRL 4eva.

8. Minka Kelly and Donald Faison:

They dated for one year in 2005. What a magical time.
Ethan Miller / Getty Images

They dated for one year in 2005. What a magical time.

9. Julie Bowen and David Spade:

They really, truly dated in 2002. And they had the same hair.
Lawrence Lucier / Getty Images

They really, truly dated in 2002. And they had the same hair.

10. Penélope Cruz and Matthew McConaughey:

Penelope was the last person Matthew dated before he met his wife Camila Alves.
Carlos Alvarez / Getty Images

Penelope was the last person Matthew dated before he met his wife Camila Alves.

11. Nick Cannon and Kim Kardashian:

The two dated for a few months in 2006 into 2007.
Ethan Miller / Getty Images

The two dated for a few months in 2006 into 2007.

12. Macaulay Culkin and Mila Kunis:

They dated for EIGHT YEARS, dude.
Ethan Miller / Getty Images

They dated for EIGHT YEARS, dude.

13. Drew Barrymore and Tom Green:

They were literally married for nine months. Life is crazy.
Lucy Nicholson / AFP / Getty Images

They were literally married for nine months. Life is crazy.

14. Conan O'Brien and Lisa Kudrow:

They dated before her big break of Friends.
Getty Images

They dated before her big break of Friends.

15. Billy Corgan and Tila Tequila:

They showed up to an award show together. Perhaps Billy wanted ~a shot at love~.
Alberto E. Rodriguez / Getty Images

They showed up to an award show together. Perhaps Billy wanted ~a shot at love~.

16. Courteney Cox and Michael Keaton:

They were together for six years!
Diane Freed / Getty Images

They were together for six years!

17. Sheryl Crow and Owen Wilson:

They dated from 1999 to 2001 before Sheryl began dating Lance Armstrong. Hollywood is amazing.
Vince Bucci / Getty Images

They dated from 1999 to 2001 before Sheryl began dating Lance Armstrong. Hollywood is amazing.

CORRECTION

Sheryl Crow and Lance Armstrong were engaged but never married. A previous version of this post misstated the status of their relationship.

CORRECTION

Ryan Gosling's and Milo Ventimiglia's last names were misspelled in a previous version of this post.

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