67 Couples Who Were Dating In 2004 That Are Super Weird To See 20 Years Later

Well, it’s official: 2004 was 20 years ago. Because this is what we do here, let’s look at all the celebrity couples dating back then that definitely aren’t right now…

4.

Alanis Morissette and Ryan Reynolds

5.

Ricky Martin and Rebecca De Alba

6.

Kirsten Dunst and Jake Gyllenhaal

7.

Serena Williams and Brett Ratner

8.

Anne Hathaway and Raffaello Follieri

9.

Justin Timberlake and Cameron Diaz

10.

Ashton Kutcher and Demi Moore

11.

Chris Pratt and Emily VanCamp

12.

Ashlee Simpson and Ryan Cabrera

13.

Adam Brody and Rachel Bilson

14.

January Jones and Josh Groban

15.

Mandy Moore and Andy Roddick

16.

Kate Bosworth and Orlando Bloom

17.

Jennifer Aniston and Brad Pitt

18.

Penélope Cruz and Tom Cruise

19.

Tiger Woods and Elin Nordegren

20.

Ben Affleck and Jennifer Garner

21.

Nicky Hilton and Ian Somerhalder

22.

Travis Barker and Shanna Moakler

23.

Sarah Silverman and Jimmy Kimmel

24.

Usher and Naomi Campbell

25.

Robin Wright and Sean Penn

26.

Keira Knightley and Jamie Dornan

27.

Ben Harper and Laura Dern

28.

Jude Law and Sienna Miller

29.

David Schwimmer and Carla Alapont

30.

Jessica Simpson and Nick Lachey

31.

Adam Goldberg and Christina Ricci

32.

Gwen Stefani and Gavin Rossdale

33.

David Duchovny and Tea Leoni

34.

Heather McComb and James Van Der Beek

35.

Ryan Phillippe and Reese Witherspoon

36.

Tommy Lee and Pamela Anderson

37.

Simon Cowell and Terri Seymour

38.

Chris Robinson and Kate Hudson

39.

Drew Barrymore and Fabrizio Moretti

40.

LeAnn Rimes and Dean Sheremet

41.

Madonna and Guy Ritchie

42.

Chad Lowe and Hilary Swank

43.

Lucy Liu and Zach Helm

44.

Britney Spears and Kevin Federline

45.

Donald Trump Jr. and Vanessa Haydon

46.

Wilmer Valderrama and Lindsay Lohan

47.

Ellen DeGeneres and Alexandra Hedison

48.

Rebecca Romijn and John Stamos

49.

Katie Holmes and Chris Klein

50.

Jermaine Dupri and Janet Jackson

51.

Mischa Barton and Brandon Davis

52.

Paris Hilton and Nick Carter

53.

Lance Armstrong and Sheryl Crow

54.

Alice Kim and Nicolas Cage

55.

Kimora Lee Simmons and Russell Simmons

56.

Ryan Seacrest and Shana Wall

57.

Charlie Sheen and Denise Richards

58.

Kate Beckinsale and Len Wiseman

59.

Dave Navarro and Carmen Electra

60.

Star Jones and Al Reynolds

61.

Marc Anthony and Jennifer Lopez

62.

Kelis and Nas

63.

Courteney Cox and David Arquette

64.

Kelli O’Donnell and Rosie O’Donnell

65.

Heidi Klum and Seal

66.

Sophia Bush and Chad Michael Murray

67.

And lastly, Brigitte Nielsen and Flavor Flav