1. Ashton Kutcher and Brittany Murphy
The two dated briefly in 2003 after meeting on the set of their rom-com, Just Married.
In 2009, following Murphy’s death, Kutcher took to Twitter to express his sadness, tweeting, “2day the world lost a little piece of sunshine. My deepest condolences go out 2 Brittany’s family, her husband, & her amazing mother Sharon. See you on the other side, kid.”
2. Jared Leto and Cameron Diaz
Leto and Diaz first began dating in 1999, and became engaged in 2000. The two called it quits suddenly in 2003.
Fortunately for Diaz, she wasn’t alone for too long: she began dating Justin Timberlake that same year.
3. Ryan Gosling and Sandra Bullock
Ryan Gosling’s first high profile romance wasn’t with Rachel McAdams, but rather with Sandra Bullock. The two met in 2002, on the set of their film, Murder By Numbers, and dated for about a year.
4. Edward Norton and Salma Hayek
Following his break-up with Courtney Love in 1999, Norton began a four year relationship with Hayek — after being set up by their chiropractor.
The pair called it quits in 2003.
5. Kim Kardashian and Nick Cannon
The two dated briefly from Sept. 2006 to Jan. 2007.
Cannon told Howard Stern in 2012, that the reason for their break-up was because Kardashian had lied about the existence of her now infamous sex tape.
6. Anne Hathaway and Topher Grace
Grace and Hathaway reportedly dated from 1999 to 2001. The two remain friends and even co-starred in the 2010 film, Valentine’s Day, together.
7. Justin Timberlake and Alyssa Milano
The two had been rumored to have dated for a few months in 2002.
In Sept. 2013, Milano confirmed the long standing rumor of their brief relationship, saying, “Yeah that’s true, that was right after Britney broke his heart, I swooped in for the kill!”
8. Ryan Reynolds and Alanis Morissette
Reynolds and Morissette began dating in 2002 and became engaged in 2004. After five years together the pair called off their engagement in 2007.
Soon after the end of their relationship, Reynolds (and his abs) began dating Scarlett Johansson. While Morissette turned her grief into music, releasing the album Flavors of Entanglement in 2008.
9. Moby and Natalie Portman
Moby and Portman dated briefly in 2001.
Surprisingly, Moby faced backlash over his relationship with Portman, he told Spin in 2008:
“But as far as the very brief affair I had with Natalie, it’s made me the target of a lot of nerd wrath. You can’t date Luke Skywalker’s mom and not have them hate your guts.”
10. Orlando Bloom and Kate Bosworth
The two dated on-and-off from 2002 to 2006.
11. Wilmer Valderrama and Mandy Moore
Was there a teen star Valderrama didn’t date in the early ’00s? The pair dated from 2001 to 2002.
In 2006, in a classy move, Valderrama opened up about their relationship on Howard Stern, claiming, among other things, that he took her virginity and that she was not like warm apple pie.
12. Carson Daly and Tara Reid
The TRL host and the party girl/actress were hot and heavy in 2000. They even became engaged a few months into their relationship.
The pair called off their engagement the following year. In 2012, Daly told Elle magazine:
“To some extent, I dodged a bullet. I was getting serious about my career, and she wanted to shoot movies and just party in her time off. That didn’t work for me.”
13. Drew Barrymore and Tom Green
After dating less than a year the two eloped in March 2001. They filed for divorce in December of that same year.
14. Scarlett Johansson and Josh Hartnett
The pair dated for about a year after meeting on the set of their 2006 film, The Black Dahlia.
15. Kirsten Dunst and Jake Gyllenhaal
The two were in a serious relationship from 2002-2004.
In 2012, Dunst opened up about Gyllenhaal, telling Allure magazine, “It would be nice to see him, but we’re not good friends.”
16. Britney Spears and Colin Farrell
The two had a brief fling in 2003.
17. Mariah Carey and Luis Miguel
Carey dated the Mexican singer, Miguel, from 1998-2001. She allegedly suffered a nervous breakdown following their break-up.
18. Naomi Watts and Heath Ledger
Ledger and Watts had a two-year relationship, which ended in 2004.
In 2011, three years after Ledger’s death from an accidental drug overdose, Watts opened up to More magazine about their relationship, saying:
“We had a beautiful relationship, only a couple of years, but he was a man who was completely full of joy, and there was a lot of laughing and affection. He was really a very special soul and made a great impact on my life. And a great actor, but I know there was so much more to come. And it’s such a tragedy for his little daughter.”
19. Rosario Dawson and Jay Z
The two reportedly dated in 2000, although neither have ever confirmed the relationship.