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See Again
© Getty Images
0 / 30 Fotos
Carlos de la Torre - Diaz met video producer Carlos de la Torre while filming an LA Gear ad. They dated from 1990 to 1994, and ended after Cameron's big break in the film 'The Mask.'
© BrunoPress
1 / 30 Fotos
Vince Neil - Neil, best known as the lead vocalist of heavy metal band Mötley Crüe, is rumored to have snagged some dates with Diaz in 1995.
© Getty Images
2 / 30 Fotos
Matt Dillon
- These stars dated for three years, from 1995 to 1998.
© Getty Images
3 / 30 Fotos
Matt Dillon - Years later, Dillon reportedly revealed that their relationship didn't work out because he wasn't ready to settle down.
© Getty Images
4 / 30 Fotos
Matt Dillon - They called it quits just after filming 'There’s Something About Mary.'
© BrunoPress
5 / 30 Fotos
Edward Norton - The two were spotted getting cozy during the Super Bowl weekend in 1999, but neither confirmed nor denied the relationship.
© Getty Images
6 / 30 Fotos
Jared Leto
- They started as friends, but ended up dating from 1999 to 2003, keeping their relationship quite private. They did, however, become engaged at one point. It's rumored they ended things when both of their careers had started to take off.
© BrunoPress
7 / 30 Fotos
Robbie Williams - Diaz is rumored to have had a brief fling with the British pop star back in 2003.
© Getty Images
8 / 30 Fotos
Justin Timberlake - The two reportedly met at the 2003 Kids Choice Awards, where Diaz awarded him for having the "Best Burp." They dated for three years after that!
© Getty Images
9 / 30 Fotos
Justin Timberlake - When they were dating, Diaz won a defamation suit against the National Enquirer after they published a front page feature announcing that she was cheating on Timberlake.
© Getty Images
10 / 30 Fotos
Justin Timberlake - Though they broke up in 2006, they teamed up again in 2010 for the movie 'Bad Teacher.' Diaz told Ellen DeGeneres, “We’re still in each other’s lives. When you care about somebody, you just want them to be happy and that’s what we both are now.”
© BrunoPress
11 / 30 Fotos
Jude Law - The two were rumored to have dated from 2006 to 2007, shortly after ‘The Holiday’ was released. It turns out they had better chemistry on-screen!
© BrunoPress
12 / 30 Fotos
John Mayer - In 2007, Diaz was spotted snuggling up to the singer in NYC's Bowery Hotel, though Mayer claims they were never dating.
© Getty Images
13 / 30 Fotos
Tyrese Gibson - Diaz is rumored to have dated Gibson—a man of many talents, from singing and rapping to acting, modeling, and producing—in the seemingly fruitful year of 2007.
© Getty Images
14 / 30 Fotos
Criss Angel - Also in 2007, Diaz was spotted going to dinners and shows in Las Vegas with none other than the Mind Freak. They reportedly only went on a couple dates, then called it quits when she left for her ‘Shrek’ tour.
© Getty Images
15 / 30 Fotos
Kelly Slater - Diaz briefly dated the professional surfer and World Surf League champion in 2007.
© BrunoPress
16 / 30 Fotos
Bradley Cooper - The two were spotted strolling NYC arm-in -arm repeatedly from 2007 to 2008, sparking rumors that Cooper tried to shut down, as he was married to Jennifer Esposito at the time. However, he and Esposito separated soon after.
© Getty Images
17 / 30 Fotos
Sean Combs (P. Diddy) - The two allegedly dated in 2008, which is when they were spotted here sharing a hug at a Los Angeles Lakers vs San Antonio Spurs game.
© Getty Images
18 / 30 Fotos
Gerard Butler - It's rumored the actors had a brief fling in 2008, but it's probably best they didn't stick together—Hollywood wouldn't be able to handle their beauty!
© Getty Images
19 / 30 Fotos
Paul Sculfor - Diaz dated the British model for about a year, from 2008 to 2009.
© Getty Images
20 / 30 Fotos
Paul Sculfor - The distance was apparently too much for them, but they remained friends afterwards. Again, it's probably best, because they set the bar way too high for couples.
© BrunoPress
21 / 30 Fotos
Keanu Reeves - The actors had starred in the 1996 crime drama ‘Feeling Minnesota' together, but they were rumored to have dated years later, from 2009 to 2010.
© BrunoPress
22 / 30 Fotos
Adam Levine - The two were rumored to be an item after Diaz was spotted introducing Levine to her mother during a lunch at Chateau Marmont.
© BrunoPress
23 / 30 Fotos
Alex Rodriguez - Diaz met the superstar baseball player at Sean Comb's Super Bowl party in 2010. They dated for about a year after that. Pictured is their awkward initial small talk!
© Getty Images
24 / 30 Fotos
Alex Rodriguez - A-Rod had recently split from Kate Hudson, but apparently preferred to keep dating A-list Hollywood actresses.
© BrunoPress
25 / 30 Fotos
Elon Musk - The two reportedly dated briefly in 2013 after it had taken Diaz an unusually long amount of time to purchase a Tesla from the CEO and billionaire.
© Getty Images
26 / 30 Fotos
Benji Madden - Finally, Cameron Diaz started dating the lead guitarist and backing vocalist for the band Good Charlotte in May of 2014.
© BrunoPress
27 / 30 Fotos
Benji Madden - The two were married in 2015, and in late 2019 welcomed a baby girl named Raddix!
© BrunoPress
28 / 30 Fotos
And they lived happily ever after...
- Diaz has proven that love takes a lot of time and a lot of different tries, but that it's ultimately worth it. See also: Celebrities' secrets to long-lasting relationships
© BrunoPress
29 / 30 Fotos
© Getty Images
0 / 30 Fotos
Carlos de la Torre - Diaz met video producer Carlos de la Torre while filming an LA Gear ad. They dated from 1990 to 1994, and ended after Cameron's big break in the film 'The Mask.'
© BrunoPress
1 / 30 Fotos
Vince Neil - Neil, best known as the lead vocalist of heavy metal band Mötley Crüe, is rumored to have snagged some dates with Diaz in 1995.
© Getty Images
2 / 30 Fotos
Matt Dillon
- These stars dated for three years, from 1995 to 1998.
© Getty Images
3 / 30 Fotos
Matt Dillon - Years later, Dillon reportedly revealed that their relationship didn't work out because he wasn't ready to settle down.
© Getty Images
4 / 30 Fotos
Matt Dillon - They called it quits just after filming 'There’s Something About Mary.'
© BrunoPress
5 / 30 Fotos
Edward Norton - The two were spotted getting cozy during the Super Bowl weekend in 1999, but neither confirmed nor denied the relationship.
© Getty Images
6 / 30 Fotos
Jared Leto
- They started as friends, but ended up dating from 1999 to 2003, keeping their relationship quite private. They did, however, become engaged at one point. It's rumored they ended things when both of their careers had started to take off.
© BrunoPress
7 / 30 Fotos
Robbie Williams - Diaz is rumored to have had a brief fling with the British pop star back in 2003.
© Getty Images
8 / 30 Fotos
Justin Timberlake - The two reportedly met at the 2003 Kids Choice Awards, where Diaz awarded him for having the "Best Burp." They dated for three years after that!
© Getty Images
9 / 30 Fotos
Justin Timberlake - When they were dating, Diaz won a defamation suit against the National Enquirer after they published a front page feature announcing that she was cheating on Timberlake.
© Getty Images
10 / 30 Fotos
Justin Timberlake - Though they broke up in 2006, they teamed up again in 2010 for the movie 'Bad Teacher.' Diaz told Ellen DeGeneres, “We’re still in each other’s lives. When you care about somebody, you just want them to be happy and that’s what we both are now.”
© BrunoPress
11 / 30 Fotos
Jude Law - The two were rumored to have dated from 2006 to 2007, shortly after ‘The Holiday’ was released. It turns out they had better chemistry on-screen!
© BrunoPress
12 / 30 Fotos
John Mayer - In 2007, Diaz was spotted snuggling up to the singer in NYC's Bowery Hotel, though Mayer claims they were never dating.
© Getty Images
13 / 30 Fotos
Tyrese Gibson - Diaz is rumored to have dated Gibson—a man of many talents, from singing and rapping to acting, modeling, and producing—in the seemingly fruitful year of 2007.
© Getty Images
14 / 30 Fotos
Criss Angel - Also in 2007, Diaz was spotted going to dinners and shows in Las Vegas with none other than the Mind Freak. They reportedly only went on a couple dates, then called it quits when she left for her ‘Shrek’ tour.
© Getty Images
15 / 30 Fotos
Kelly Slater - Diaz briefly dated the professional surfer and World Surf League champion in 2007.
© BrunoPress
16 / 30 Fotos
Bradley Cooper - The two were spotted strolling NYC arm-in -arm repeatedly from 2007 to 2008, sparking rumors that Cooper tried to shut down, as he was married to Jennifer Esposito at the time. However, he and Esposito separated soon after.
© Getty Images
17 / 30 Fotos
Sean Combs (P. Diddy) - The two allegedly dated in 2008, which is when they were spotted here sharing a hug at a Los Angeles Lakers vs San Antonio Spurs game.
© Getty Images
18 / 30 Fotos
Gerard Butler - It's rumored the actors had a brief fling in 2008, but it's probably best they didn't stick together—Hollywood wouldn't be able to handle their beauty!
© Getty Images
19 / 30 Fotos
Paul Sculfor - Diaz dated the British model for about a year, from 2008 to 2009.
© Getty Images
20 / 30 Fotos
Paul Sculfor - The distance was apparently too much for them, but they remained friends afterwards. Again, it's probably best, because they set the bar way too high for couples.
© BrunoPress
21 / 30 Fotos
Keanu Reeves - The actors had starred in the 1996 crime drama ‘Feeling Minnesota' together, but they were rumored to have dated years later, from 2009 to 2010.
© BrunoPress
22 / 30 Fotos
Adam Levine - The two were rumored to be an item after Diaz was spotted introducing Levine to her mother during a lunch at Chateau Marmont.
© BrunoPress
23 / 30 Fotos
Alex Rodriguez - Diaz met the superstar baseball player at Sean Comb's Super Bowl party in 2010. They dated for about a year after that. Pictured is their awkward initial small talk!
© Getty Images
24 / 30 Fotos
Alex Rodriguez - A-Rod had recently split from Kate Hudson, but apparently preferred to keep dating A-list Hollywood actresses.
© BrunoPress
25 / 30 Fotos
Elon Musk - The two reportedly dated briefly in 2013 after it had taken Diaz an unusually long amount of time to purchase a Tesla from the CEO and billionaire.
© Getty Images
26 / 30 Fotos
Benji Madden - Finally, Cameron Diaz started dating the lead guitarist and backing vocalist for the band Good Charlotte in May of 2014.
© BrunoPress
27 / 30 Fotos
Benji Madden - The two were married in 2015, and in late 2019 welcomed a baby girl named Raddix!
© BrunoPress
28 / 30 Fotos
And they lived happily ever after...
- Diaz has proven that love takes a lot of time and a lot of different tries, but that it's ultimately worth it. See also: Celebrities' secrets to long-lasting relationships
© BrunoPress
29 / 30 Fotos
Is your list of ex-boyfriends just as impressive as Cameron Diaz's?
It’s almost as long as her filmography!
© Getty Images
There really is something about Mary! It may come as no surprise—considering that the attractive star is also a very talented actress—that Cameron Diaz has an extensive romantic past, but it’s really a list that deserves a thorough look. Check out this gallery to learn about this Angel's history of love.
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