20 Chaotic Celebrity Couples From The Early Aughts We Tried Desperately To Forget
There was A LOT going on in the world in the early 2000s. The world was in major flux, and culturally, we were in a really weird moment.
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Weird energy and weird vibes bring forth weird couples. Some of these pairings from the early aughts show you just how totally strange of a time it was.
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1.Matt Damon and Winona Ryder were set up by Gwyneth Paltrow in 1998. The two made it into the new millennium but called it quits in spring 2000.
2.Topher Grace and Anne Hathaway were both in the early days of their careers when they got together in 1999. They called it quits in the summer of 2001.
3.In 1999, Salma Hayek and Edward Norton were set up (allegedly by their chiropractor!). They dated for four years, until 2003.
4.Angelina Jolie and Billy Bob Thornton met in 1999, and got married in 2000...while he was engaged to Laura Dern.
There were vials of blood and matching tattoos and, in 2003, a divorce over their differing personalities.
5.Drew Barrymore and Tom Green met on the set of Charlie's Angels in 2000 and fell for each other. No one understood their dynamic, but that didn't stop them from tying the knot in 2001. Sadly, it only lasted nine months.
6.Carson Daly and Tara Reid met during MTV Spring Break in 2000 and got engaged that fall, but they never made it to the altar. The relationship ended in the summer of 2001.
7.Denise Richards and Charlie Sheen met in 2000 and started dating the next year when she did a guest spot on Spin City. They got married in 2002 and went through some ups and downs as they welcomed two girls, Sam and Lola.
They divorced in spring 2006.
8.Wilmer Valderrama and Mandy Moore were an item from 2000 to 2002, but Wilmer did a lot of interesting dating in the '00s.
9.Sandra Bullock and Ryan Gosling dated after filming Murder by Numbers together in 2002. They called it quits after nearly two years together.
10.Janet Jackson and Matthew McConaughey dated briefly in 2002...according to her. He says they were just friends.
11.Megan Fox dated 7th Heaven star David Gallagher from 2002 to 2003. He was allegedly her first love.
12.Macaulay Culkin and Mila Kunis's eight-year relationship began in 2002. The couple struggled for privacy due to the rabid nature of Macaulay's early career fans.
13.Ryan Reynolds and Alanis Morissette were a match made in Canadian heaven that got started in 2002. They even almost got married but called it quits in 2007.
14.That very same timeline saw Jared Leto and Cameron Diaz get together, get engaged, and call it quits.
15.Flavor Flav and Brigitte Nielsen met on The Surreal Life in 2003 and ended up together. They landed their own spinoff, Strange Love, and it ended with them ending in 2005.
16.Christopher Knight and model Adrianne Curry also ended up with a Surreal Life spinoff, My Fair Brady. They were together from 2004 to 2011, announcing their split on their fifth wedding anniversary.
17.Wilmer Valderrama was back in 2004, dating a not-yet-18 Lindsay Lohan. In two months, they got together, got engaged, and called it quits.
18.Nick Carter and Paris Hilton dated for just seven months in 2004, but it entailed countless headlines for hard partying and, sadly, alleged abuse.
19.Britney Spears and Kevin Federline met in 2004 and married that same year. The pop star and professional dancer struggled throughout their relationship before calling it quits in 2007.
They have two kids together: Sean Preston and Jayden James.
20.Hilary Duff and Joel Madden were another odd couple to come out of 2004. It was controversial considering she was 16 and he was 25 when they started dating. They split in 2006.
