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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.'

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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.

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Matt Dillon -

These stars dated for three years, from 1995 to 1998.

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Matt Dillon - Years later, Dillon reportedly revealed that their relationship didn't work out because he wasn't ready to settle down.

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Matt Dillon - They called it quits just after filming 'There’s Something About Mary.'

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Edward Norton - The two were spotted getting cozy during the Super Bowl weekend in 1999, but neither confirmed nor denied the relationship.

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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.

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Robbie Williams - Diaz is rumored to have had a brief fling with the British pop star back in 2003. 

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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!

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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.

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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.”

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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!

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John Mayer - In 2007, Diaz was spotted snuggling up to the singer in NYC's Bowery Hotel, though Mayer claims they were never dating.

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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.

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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.

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Kelly Slater - Diaz briefly dated the professional surfer and World Surf League champion in 2007. 

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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.

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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.

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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!

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Paul Sculfor - Diaz dated the British model for about a year, from 2008 to 2009.

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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.

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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.

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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.

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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!

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Alex Rodriguez - A-Rod had recently split from Kate Hudson, but apparently preferred to keep dating A-list Hollywood actresses.

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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.

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Benji Madden - Finally, Cameron Diaz started dating the lead guitarist and backing vocalist for the band Good Charlotte in May of 2014.

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Benji Madden - The two were married in 2015, and in late 2019 welcomed a baby girl named Raddix!

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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

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