The year was 2003. New York Daily News Archive / NY Daily News via Getty Images
Faux hawks and bejeweled flip phones were the peak of high fashion. New York Daily News Archive / NY Daily News via Getty Images
Disposable cameras were a necessity, not a $25 hipster hobby sold at Urban Outfitters. The Washington Post / The Washington Post via Getty Images
These two scoundrels were wanted for robbing a Hot Topic. Anthony Harvey - Pa Images / PA Images via Getty Images
And all of these random couples dated... 1. Alanis Morissette and Ryan Reynolds: Kevin Winter / Getty Images
2. 50 Cent and Vivica A. Fox: Jeff Kravitz / FilmMagic / Getty Images
3. Ricky Martin and Rebecca de Alba: Gregory Pace / FilmMagic / Getty Images
4. Tiger Woods and Elin Nordegren: Timothy A. Clary / AFP via Getty Images
5. Eric Benét and Halle Berry: Vince Bucci / Getty Images
6. Travis Barker and Shanna Moakler: Steve Granitz / WireImage / Getty Images
7. Demi Moore and Ashton Kutcher: Albert L. Ortega / WireImage / Getty Images
8. Kylie Minogue and Olivier Martinez: Bertrand Rindoff Petroff / Getty Images
9. Sarah Silverman and Jimmy Kimmel: Jon Kopaloff / FilmMagic / Getty Images
10. David Schwimmer and Carla Alaponte: J. Vespa / WireImage / Getty Images
11. Lance Bass and girlfriend Carrah: Dimitrios Kambouris / WireImage / Getty Images
12. Mary-Kate Olsen and an "unidentified boyfriend": Vince Bucci / Getty Images
13. Star Jones and Al Reynolds: Paul Hawthorne / WireImage for ESPN the Magazine / Getty Images
14. Kirsten Dunst and Jake Gyllenhaal: Bauer-griffin / GC Images / Getty Images
15. David Duchovny and Tea Leoni: Jeff Kravitz / FilmMagic, Inc / Getty Images
16. Helena Bonham Carter and Tim Burton: Sylvain Gaboury / FilmMagic / Getty Images
17. Jessica Alba and Michael Weatherly: Gregg Deguire / WireImage / Getty Images
18. Katie Holmes and Chris Klein: Gregory Pace / FilmMagic / Getty Images
19. Deryck Whibley and Paris Hilton: Rodrigo Varela / WireImage / Getty Images
20. Narvel Blackstock and Reba McEntire: Matthew Peyton / Getty Images
21. Heather McComb and James Van Der Beek: Gregg Deguire / WireImage / Getty Images
22. Ashley Scott and Ashton Kutcher: Steve Granitz / WireImage / Getty Images
23. Uma Thurman and Ethan Hawke: Djamilla Rosa Cochran / WireImage / Getty Images
24. Ben Harper and Laura Dern: Steve Granitz / WireImage / Getty Images
25. Camille Grammer and Kelsey Grammer: Jeff Kravitz / FilmMagic, Inc / Getty Images
26. Nick Lachey and Jessica Simpson: Kmazur / WireImage for Clear Channel Entertainment
27. Brendan Fraser and Afton Smith: Jon Kopaloff / FilmMagic / Getty Images
28. Chris Robinson and Kate Hudson: R. Diamond / WireImage / Getty Images
29. Scott Foley and Jennifer Garner: Frank Trapper / Corbis via Getty Images
30. Gavin Rossdale and Gwen Stefani: Steve Granitz / WireImage / Getty Images
31. Daniel Zelman and Debra Messing: Chris Weeks / FilmMagic / Getty Images
32. Morgan Freeman and Myrna Colley-Lee: J.P. Aussenard / WireImage / Getty Images
33. Russell Simmons and Kimora Lee Simmons: Vinnie Zuffante / Getty Images
34. Britney Spears and Colin Farrell: Kevin Winter / Getty Images
35. Justin Timberlake and Cameron Diaz: Bauer-griffin / GC Images / Getty Images
36. Carmen Electra and Dave Navarro: Kmazur / WireImage / Getty Images
37. Ty Murray and Jewel: Chris Farina / Corbis via Getty Images
38. Drew Barrymore and Fabrizio Moretti: James Devaney / WireImage / Getty images
39. Courteney Cox and David Arquette: James Devaney / WireImage / Getty Images
40. Penélope Cruz and Tom Cruise: Frank Trapper / Corbis via Getty Images
41. Salman Rushdie and Padma Lakshmi: Jim Spellman / WireImage / Getty Images
42. Edward Norton and Salma Hayek: Ron Galella / Ron Galella Collection via Getty Images
43. Ellen DeGeneres and Alexandra Hedison: J. Vespa / WireImage / Getty Images
44. Janet Jackson and Jermaine Dupri: R. Diamond / WireImage / Getty Images
45. Tammy Lynn Michaels and Melissa Etheridge: Jon Kopaloff / FilmMagic / Getty Images
46. Elisha Cuthbert and Andrew Keegan: Fairchild Archive / Penske Media via Getty Images
47. Kid Rock and Pamela Anderson: Gregg Deguire / WireImage / Getty Images
48. Danny Mozes and Cynthia Nixon: Robin Platzer / FilmMagic / Getty Images
49. Madonna and Guy Ritchie: Kmazur / WireImage / Getty Images
50. Usher and Chilli: Jean-paul Aussenard / WireImage / Getty Images
51. LeAnn Rimes and Dean Sheremet: M. Von Holden / FilmMagic / Getty Images
52. Charlie Sheen and Denise Richards: Walter Mcbride / Corbis via Getty Images
53. Ryan Phillippe and Reese Witherspoon: Sylvain Gaboury / FilmMagic / Getty Images
54. Chad Lowe and Hilary Swank: Gregory Pace / FilmMagic / Getty Images
55. Rebecca Romijn and John Stamos: Bruce Glikas / FilmMagic / Getty Images
56. Robin Wright and Sean Penn: J. Vespa / WireImage / Getty Images
57. Matthew Perry and Rachel Dunn: Robert Laberge / Getty Images
58. Lucy Liu and Zach Helm: Dimitrios Kambouris / WireImage for Miramax Films / Getty Images
59. Lance Armstrong and Sheryl Crow: Vinnie Zuffante / Getty Images
60. Adam Brody and Rachel Bilson: J. Vespa / WireImage / Getty Images
61. Kelis and Nas: Djamilla Rosa Cochran / WireImage / Getty Images
62. Heidi Klum and Seal: Evan Agostini / Getty Images
63. And last but not least, Jennifer Aniston and Brad Pitt: Jeff Kravitz / FilmMagic, Inc / Getty Images
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