The Most Random Celebrity Couples From The ’90s And Early 2000s


There is life after random love.

1.

Megan Fox and David Gallagher (the kid from 7th Heaven) dated.


Chris Walter / WireImage / Getty Images

They were together 2003-04.


Gregg Deguire / WireImage

Now she’s engaged to Machine Gun Kelly.


Udo Salters / Patrick McMullan via Getty Images

And the most recent pic I could find of David was from 2011. ¯\_(ツ)_/¯


Gregg Deguire / FilmMagic

2.

January Jones and Josh Groban dated.


Vince Bucci / Getty Images

They were together 2004-06.


Jeffrey Mayer / WireImage

Now she’s a mom to her son, Xander.


David Livingston / Getty Images

And Josh is in a relationship with actor Schuyler Helford.


Bruce Glikas / Bruce Glikas / WireImage

3.

Paris Hilton and Deryck Whibley (the lead singer of Sum 41) dated.

They were together for a few months in 2003.


Rodrigo Varela / WireImage

Now she’s married to Carter Reum. He’s a venture capitalist/author.

And Deryck is married to model Ariana Cooper, and they have a son.

4.

Scarlett Johansson and Jack Antonoff dated.


Evan Agostini / Getty Images

They were together 2001-02.


Evan Agostini / Getty Images

Now Scarlett is married to SNL writer Colin Jost.

And Jack is dating actor Margaret Qualley.


Michael Kovac / Getty Images for AFI

5.

Topher Grace and Anne Hathaway dated.

They were together 1999-2001.


J. P. Aussenard / WireImage

Now Anne is married to jewelry designer and producer Adam Shulman.


Daniele Venturelli / WireImage

And Topher is married to actor Ashley Hinshaw.


Daniele Venturelli / WireImage

6.

Jennifer Aniston and Tate Donovan dated.

They were together 1995-98.


Ron Galella, Ltd. / Ron Galella Collection via Getty Images

7.

Sandra Bullock also dated Tate Donovan. That makes her and Jennifer Aniston spit sisters :).


Ron Galella / Ron Galella Collection via Getty Images

They were together for four years.


Vinnie Zuffante / Getty Images

8.

Also, Sandra Bullock and Ryan Gosling were a couple.


Sylvain Gaboury / FilmMagic

They dated 2001-02.


Ron Galella, Ltd. / Ron Galella Collection via Getty Images

These days, Jennifer Aniston and Sandra Bullock are living their best lives.


Charley Gallay / Getty Images for Netflix

Tate Donovan is a silver fox.

And Ryan Gosling is married to Eva Mendes, and they have two kids.


Sonia Recchia / Getty Images

9.

Jessica Biel and Chris Evans dated.


Gregg Deguire / WireImage

They were together 2001-06…five years!


Steve Granitz / WireImage

Now Jessica is married to Justin Timberlake.


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And Chris Evans is Chris Evans.


Jerod Harris / Getty Images

10.

Jamie Dornan and Keira Knightley dated.


Dave M. Benett / Getty Images

They were together 2003-05.


Antony Jones / UK Press via Getty Images

Now Jamie is married to composer Amelia Warner.


Arturo Holmes / FilmMagic

And Keira is married to musician James Righton, and they have two kids.


Stephane Cardinale – Corbis / Corbis via Getty Images

11.

Alanis Morissette and Ryan Reynolds dated and were engaged.

They were together 2002-06.


Jeffrey Mayer / WireImage

Now Ryan is married to Blake Lively.


Jamie Mccarthy / Getty Images

And Alanis is married to rapper Souleye.


Bruce Glikas / Bruce Glikas / FilmMagic

12.

Mila Kunis and Macaulay Culkin dated.


Dimitrios Kambouris / WireImage

They were together 2002-11.


Ethan Miller / Getty Images

Now Mila is married to Ashton Kutcher.


David Livingston / FilmMagic

And Macaulay is engaged to Brenda Song, and they have a child together.


Kevin Mazur / Getty Images for Stand Up To Cancer

13.

Emily Blunt and Michael Bublé dated.


George Pimentel / WireImage

They were together 2005-08.


Michael Loccisano / FilmMagic

Now Emily is married to John Krasinski.


Roy Rochlin / Getty Images for Paramount Pictures

And Michael is married to model Luisana Lopilato.


Lester Cohen / Getty Images for Warner Bros Records

14.

Luke Wilson and Drew Barrymore dated.


Ron Galella, Ltd. / Ron Galella Collection via Getty Images

They were together 1997-99.


Ron Galella, Ltd. / Ron Galella Collection via Getty Images

Now Drew is recently divorced and thriving.

And Luke is doing whatever Luke does.


Richard Rodriguez / Getty Images for Sony Pictures Classics

15.

Bow Wow and Ciara dated.


Marsaili Mcgrath / Getty Images

They were together 2004-06.

Now Ciara is married to Russell Wilson.


Arturo Holmes / FilmMagic

And TBH, I don’t know Bow Wow’s relationship status.


Marcus Ingram / Getty Images

16.

Cameron Diaz and Jared Leto dated.

They were together 1999-2003.


Fafl / FameFlynet / BACKGRID

Now Cameron Diaz is married to Benji Madden, and they have one son together.

And Jared Leto has good hair.


Lester Cohen / Getty Images for The Recording Academy

17.

Wilmer Valderrama and Mandy Moore dated.

They were together 2001-02

Now Mandy Moore is married to musician Taylor Goldsmith, and they have a child.


Kevin Mazur / Getty Images for Critics Choice Association

And Wilmer Valderama is engaged to model Amanda Pacheco, and they have one kid.


Lisa O’connor / AFP via Getty Images

18.

50 Cent and Vivica A. Fox dated.


Dave Hogan / Getty Images

They were together for a bit in 2003.

Now they are both single. Perhaps they should reignite the flame à la Bennifer.


Jamie Mccarthy / Getty Images for STARZ, Arnold Turner / Getty Images for A Manny Halley Production


19.

Heidi Klum and Red Hot Chili Peppers’ Anthony Kiedis dated.


Ben-ari Finegold / Getty Images

They were together for a couple months in 2002.


Mel Bouzad / Getty Images

Now Heidi is married to Tom Kaulitz. Yes, this Tom Kaulitz.


Steve Granitz / FilmMagic

And Anthony is seemingly currently single.


Michael Tran / AFP via Getty Images

20.

Minnie Driver and Matt Damon dated.

They were together 1997-98.

Now Matt is married to Luciana Barroso.


Arturo Holmes / Getty Images

And Minnie is with filmmaker Addison O’Dea.


Frazer Harrison / Getty Images

21.

Brooke Shields and Liam Neeson dated.


Images Press / Getty Images

They were together for a bit in 1992.


Ron Galella, Ltd. / Ron Galella Collection via Getty Images

Now Brooke is married to Chris Henchy.


Bravo / NBCU Photo Bank via Getty Images

And Liam has remained single since the death of his wife, Natasha Richardson, in 2009.


Bravo / NBCU Photo Bank via Getty Images

22.

And Finally, Kim Kardashian and Nick Cannon dated.


Michael Tran Archive / FilmMagic

They were together in 2006.

Now Kim is dating Pete Davidson.


Mape / BlayzenPhotos / BACKGRID


Shahar Azran / Getty Images



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