1. Avril Lavigne and Brody Jenner dated from 2010-2012. Jean Baptiste Lacroix / WireImage 2. Sandra Bullock and Ryan Gosling were together from 2001-2003. Sylvain Gaboury / FilmMagic 3. Deryck Whibley and Paris Hilton dated in 2003. Rodrigo Varela / WireImage 4. Julie Bowen and David Spade dated from 2002-2003. Evan Agostini / Getty Images 5. Josh Groban and January Jones were together from 2003-2006. Jeffrey Mayer / WireImage 6. And January Jones and Jeremy Piven who had a thing in 2010. Jeff Kravitz / FilmMagic 7. Taylor Lautner and Lily Collins dated sometime in 2011. Francois Durand / Getty Images 8. Jessica Biel and Chris Evans were a couple from 2001-2006. Gregg Deguire / WireImage 9. Also, Chris Evans and Christina Ricci dated briefly in 2007. Dimitrios Kambouris / WireImage 10. Anddd Christina Ricci and Adam Goldberg, who were together from 2004-2007. Gregg Deguire / WireImage for GLAAD 11. Annnddd Adam Goldberg and Natasha Lyonne, who dated from 2001-2005. Jeff Kravitz / FilmMagic, Inc 12. David Gallagher and Megan Fox dated from 2003-2004. Gregory Pace / FilmMagic 13. Ryan Phillippe and Amanda Seyfried dated in 2011. 14. Emma Stone and Kieran Culkin were together in 2009. Matt Winkelmeyer / Getty Images for The Met Museum/Vogue 15. Nicky Hilton and Ian Somerhalder dated in 2004. Arnaldo Magnani / Getty Images 16. Stacy Keibler and George Clooney were together from 2011-2013. Dimitrios Kambouris / WireImage 17. Kristen Johnston and Ryan Reynolds dated in 1999. Frank Trapper / Corbis via Getty Images 18. Zoë Kravitz and Penn Badgley were together from 2011-2013. Alo Ceballos / FilmMagic 19. Mandy Moore and Andy Roddick dated from 2002-2004. Jim Spellman / WireImage for Harrison & Shriftm 20. Ashley Greene and Joe Jonas dated from 2010-2011. Denise Truscello / WireImage 21. Ryan Seacrest and Julianne Hough were together from 2010-2013. Todd Williamson / WireImage 22. Aaron Paul and Samaire Armstrong (from The O.C.) dated from 2001-2002. Ray Mickshaw / WireImage 23. Blake Lively and Leonardo DiCaprio dated in 2011. Lupa / Revolver / Backgrid 24. Cameron Diaz and Alex Rodriguez dated from 2010-2011. Tiffany Rose / Getty Images 25. And Kate Hudson and Alex Rodriguez dated in 2009. Nydailynews / Getty Images 26. Naomi Campbell and Usher dated in 2004. Kmazur / WireImage 27. Topher Grace and Anne Hathaway were together from 1999-2001. J. P. Aussenard / WireImage 28. Ellen DeGeneres and Alexandra Hedison were together from 2001-2004. Jeff Kravitz / FilmMagic 29. Cristiano Ronaldo and Irina Shayk were together from 2010-2015. Denis Doyle / Getty Images 30. Kristen Stewart and Michael Angarano were together from 2005-2008. Jeff Kravitz / FilmMagic 31. Russell Brand and Katy Perry were married and divorced between 2010-2011. Dave M. Benett / Getty Images 32. Chord Overstreet and Emma Roberts dated from 2011-2012. Handout / Getty Images 33. Lewis Hamilton and Nicole Scherzinger were together from 2008-2015. Jean Baptiste Lacroix / WireImage 34. Kris Humphries and Kim Kardashian were married and divorced between 2010-2011. Kevin Mazur / WireImage 35. Josh Duhamel and Fergie were together from 2004-2017. Kevin Winter / Getty Images 36. Dev Patel and Freida Pinto were together from 2008-2014. Joe Scarnici / Getty Images for BlackBerry 37. Zachary Quinto and Jonathan Groff dated from 2012-2013. Matt Winkelmeyer / Getty Images for GQ 38. Kristin Davis and Liev Schreiber dated from 2000-2003. Gregory Pace / FilmMagic 39. Johnny Simmons and Emma Watson dated in 2011. 40. Sean Penn and Scarlett Johansson dated in 2011. 41. Also Sean Penn and Charlize Theron dated from 2013-2015. Thomas Niedermueller / Getty Images 42. Rosario Dawson and Jason Lewis dated from 2004-2006 John Parra / WireImage 43. Michael Buble and Emily Blunt were together from 2005-2008. Jeff Kravitz / FilmMagic, Inc 44. Ginnifer Goodwin and Chris Klein dated from 2006-2008. Steve Granitz / WireImage 45. Ashley Olsen and Justin Bartha were together from 2008-2011. Jason Merritt / Getty Images 46. Serena Williams and Brett Ratner dated from 2004-2006. Larry Busacca 47. Penélope Cruz and Tom Cruise were together from 2001-2004. Jim Spellman / WireImage 48. Keira Knightley and Jamie Dornan were together from 2003-2005. Niki Nikolova / FilmMagic 49. Joaquin Phoenix and Liv Tyler dated from 1997-1998. New York Daily News Archive / NY Daily News via Getty Images 50. Cherry Jones and Sarah Paulson were together from 2004-2009. Bruce Glikas / FilmMagic 51. Valentin Chmerkovskiy and Amber Rose dated in 2017. James Devaney / GC Images 52. JC Chasez and Eva Longoria dated in 2004. Jon Kopaloff / FilmMagic 53. LeAnn Rimes and Andrew Keegan were together from 1998-2001. Steve Granitz / WireImage 54. Brigitte Nielsen and Flavor Flav dated in 2004. J. Merritt / FilmMagic 55. Colin Hanks and Busy Philipps dated in 1997. Ron Galella / Ron Galella Collection via Getty Images 56. Fiona Shaw and Saffron Burrows were together from 2002-2005. 57. John Mayer and Jennifer Love Hewitt dated in 2002. 58. And John Mayer and Minka Kelly dated in 2008. James Devaney / WireImage 59. Also John Mayer and Jennifer Aniston dated from 2008-2009. Kevin Mazur / WireImage 60. Jerry O'Connell and Giuliana Rancic (when she was Giuliana DePandi) dated from 2003-2004. Jon Kopaloff / FilmMagic 61. And finally, Helena Bonham Carter and Steve Martin dated in 2001.