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

1.

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

They were together 2003-04.

Now she’s engaged to Machine Gun Kelly.

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

2.

January Jones and Josh Groban dated.

They were together 2004-06.

Now she’s a mom to her son, Xander.

And Josh is in a relationship with actor Schuyler Helford.

3.

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

They were together for a few months in 2003.

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.

They were together 2001-02.

Now Scarlett is married to SNL writer Colin Jost.

And Jack is dating actor Margaret Qualley.

5.

Topher Grace and Anne Hathaway dated.

They were together 1999-2001.

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

And Topher is married to actor Ashley Hinshaw.

6.

Jennifer Aniston and Tate Donovan dated.

They were together 1995-98.

7.

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

They were together for four years.

8.

Also, Sandra Bullock and Ryan Gosling were a couple.

They dated 2001-02.

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

Tate Donovan is a silver fox.

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

9.

Jessica Biel and Chris Evans dated.

They were together 2001-06…five years!

Now Jessica is married to Justin Timberlake.

And Chris Evans is Chris Evans.

10.

Jamie Dornan and Keira Knightley dated.

They were together 2003-05.

Now Jamie is married to composer Amelia Warner.

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

11.

Alanis Morissette and Ryan Reynolds dated and were engaged.

They were together 2002-06.

Now Ryan is married to Blake Lively.

And Alanis is married to rapper Souleye.

12.

Mila Kunis and Macaulay Culkin dated.

They were together 2002-11.

Now Mila is married to Ashton Kutcher.

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

13.

Emily Blunt and Michael Bublé dated.

They were together 2005-08.

Now Emily is married to John Krasinski.

And Michael is married to model Luisana Lopilato.

14.

Luke Wilson and Drew Barrymore dated.

They were together 1997-99.

Now Drew is recently divorced and thriving.

And Luke is doing whatever Luke does.

15.

Bow Wow and Ciara dated.

They were together 2004-06.

Now Ciara is married to Russell Wilson.

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

16.

Cameron Diaz and Jared Leto dated.

They were together 1999-2003.

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

And Jared Leto has good hair.

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.

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

18.

50 Cent and Vivica A. Fox dated.

They were together for a bit in 2003.

19.

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

They were together for a couple months in 2002.

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

And Anthony is seemingly currently single.

20.

Minnie Driver and Matt Damon dated.

They were together 1997-98.

Now Matt is married to Luciana Barroso.

And Minnie is with filmmaker Addison O’Dea.

21.

Brooke Shields and Liam Neeson dated.

They were together for a bit in 1992.

Now Brooke is married to Chris Henchy.

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

22.

And Finally, Kim Kardashian and Nick Cannon dated.

They were together in 2006.

Now Kim is dating Pete Davidson.