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Updated on Aug 6, 2020. Posted on Aug 3, 2020

14 Weird And Iconic Couples Of The Early 2000s: Then And Now, Like Who Actually Ended Up With Who

Britney Spears stays winning.

1. Aaron Carter and Hilary Duff when they were a couple in the early 2000s:

Lucy Nicholson / Getty Images

Aaron Carter and his fiancé, Melanie Martin, now.

Hilary Duff and her husband, Matthew Korma, now:

2. Britney Spears and the guy from NSYNC then:

Lucy Nicholson / Getty Images

Britney Spears and her super hot physical trainer boyfriend, Sam Asghari, now:

Justin Timberlake and his wife, Jessica Biel, now:

3. Jessica Simpson and Nick Lachey as a couple then:

Brenda Chase / Getty Images

Jessica Simpson and her former professional football player husband, Eric Johnson, now:

Nick Lachey with his wife, Vanessa, now:

4. Ashlee Simpson and Ryan Cabrera then:

Frank Micelotta / Getty Images

Ryan Cabrera and his professional wrestler girlfriend, Alexa Bliss, now:

Ashlee Simpson Ross and her husband, Evan Ross (Diana Ross's son!), now:

5. Ryan Gosling and Sandra Bullock then:

Fred Prouser / Reuters

Ryan Gosling and his girlfriend, Eva Mendes, in 2012 because they have zero public presence and this is the only picture we have:

Sonia Recchia / Getty Images

Sandra Bullock and her photographer boyfriend, Bryan Randall, now:

Raymond Hall / GC Images

6. Alanis Morissette and Ryan Reynolds then:

Kevin Winter / Getty Images

Ryan Reynolds and his wife, Blake Lively, now:

Alanis Morissette and her rapper husband, Souleye, now:

7. Jennifer Lopez and Ben Affleck then:

Ezra Shaw / Getty Images

Jennifer Lopez and her fiancé, Alex Rodriguez, now:

Ben Affleck and his actor girlfriend, Ana De Armas, now:

Agny, Bens / Wagner AZ / BENS / BACKGRID

She was in Knives Out!

8. Carson Daly and Tara Reid then:

Nick Elgar / Getty Images

Tara Reid and her boyfriend, Nathan Montpetit-Howar, now:

Carson Daly with his wife and family now:

9. Winona Ryder and Matt Damon then:

Lucy Nicholson / Getty Images

Winona Ryder and her fashion designer boyfriend, Scott Mackinlay Hahn, now:

Chelsea Guglielmino / Getty Images

Matt Damon and his wife of 15 years, Luciana Barroso, now:

Nick Agro / Getty Images

10. Mandy Moore and Wilmer Valderrama then:

John Shearer / WireImage

Mandy Moore and her musician husband, Taylor Goldsmith, now:

Wilmer Valderrama and his model fiancé, Amanda Pacheco, now:

11. Gwyneth Paltrow and Brad Pitt then:

Diane Freed / Getty Images

Gwyneth Paltrow and her husband Brad Falchuk, who is the co-creator of Glee, now:

Brad Pitt's possible girlfriend, Alia Shawkat, now:

And now, just because I'm feeling random, here are three fictional couples and the people they actually ended up with...

12. Zack Morris (Mark-Paul Gosselaar) and Kelly Kapowski (Tiffani Thiessen) then:

Nbc / Getty Images

Who "Zack," Mark-Paul Gosselaar, actually ended up with:

Who "Kelly," Tiffani Thiessen, actually ended up with:

13. Chuck Bass (Ed Westwick) and Blair Waldorf (Leighton Meester) then:

James Devaney / WireImage

Who "Blair," Leighton Meester, ended up with:

Matt Winkelmeyer / Getty Images

Who "Chuck," Ed Westwick, ended up with:

14. Cory (Ben Savage) and Topanga (Danielle Fishel) then:

Brenda Chase / Getty Images

Who "Cory," Ben Savage, ended up with:

Who "Topanga," Danielle Fishel, ended up with:

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Correction:

In a previous version of this post there was a picture of Gwyneth Paltrow and some other dude. It has been fixed with her correct husband.

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