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. L. Cohen / WireImage
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. Jeff Kravitz / FilmMagic
And Deryck is married to model Ariana Cooper, and they have a son. Jeff Kravitz / FilmMagic
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. Axelle / FilmMagic
And Jack is dating actor Margaret Qualley. Michael Kovac / Getty Images for AFI
5. Topher Grace and Anne Hathaway dated. Gregory Pace / FilmMagic
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. Kmazur / WireImage
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. Leon Bennett / WireImage
And Ryan Gosling is married to Eva Mendes, and they have two kids. Sonia Recchia / Getty Images
OKAY, moving on. 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. Rodin Eckenroth / Getty Images
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. Gregory Pace / FilmMagic
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. Jason Howard / GC Images
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. Jeff Kravitz / FilmMagic
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. Jeff Kravitz / FilmMagic
They were together 1999-2003. Fafl / FameFlynet / BACKGRID
Now Cameron Diaz is married to Benji Madden, and they have one son together. Noel Vasquez / GC Images
And Jared Leto has good hair. Lester Cohen / Getty Images for The Recording Academy
17. Wilmer Valderrama and Mandy Moore dated. L. Cohen / WireImage
They were together 2001-02 John Shearer / WireImage
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. Kmazur / WireImage
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. Tom Wargacki / WireImage
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. Johnny Nunez / WireImage
Now Kim is dating Pete Davidson. Mape / BlayzenPhotos / BACKGRID
Shahar Azran / Getty Images
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