Cameron Diaz’s Love Life

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Carlos de la Torre

Remember when? Before breaking out in Hollywood, Diaz dated the video producer in the early '90s. Shortly after, she became a household name when she landed roles in 1994's blockbuster The Mask and 1997's My Best Friend's Wedding.

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Matt Dillon

The actors began dating in 1995 and split shortly after filming 1998's There's Something About Mary. In July 2006, Dillon recalled how he felt post-breakup to Parade magazine. "I was dissatisfied with where I was as a man, with my relationships, with my career. Like a lot of guys, I was driven by my work," he said. "It's a very powerful thing when you feel that way about somebody. Cameron was a muse for me. I hadn't been in any deep emotional relationships."

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Jared Leto

Pre-Oscar love! Long before his impeccable man bun, Diaz dated the Dallas Buyers Club actor and Thirty Seconds to Mars frontman from 1999 to 2003. "You have to find someone in the same place as you are. Timing is everything," Diaz told Cosmopolitan in January 2015. "We girls sometimes do the thing where we pick the same person over and over again — they look and seem different, but deep down, they're the same. And that's on us."

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Justin Timberlake

Friendliest exes ever? The Holiday actress has remained on good terms with the "Mirrors" singer since splitting in late 2006 after nearly four years of dating. They went on to costar in 2007's Shrek the Third and (have a sex scene!) in 2011's Bad Teacher. "Justin and I have always had a good laugh together," Diaz told Us that same year. "[He's] a genius comedian — he's clearly talented. We went for the best person for the job, and it just so happened that it was him."

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John Mayer

Half of his heart? The Annie actress was spotted getting to know the musician in NYC in August 2007. "It was the two of them, getting to know each other, out on the town," a source told Us. "This was technically not their first time hanging out. They've hung out together with friends before. But this was the first time together like this. It's new and developing…but they really like each other and it went well."

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Bradley Cooper

On the down low! In September 2007, Diaz was photographed with the Silver Linings Playbook actor at the New York Giants vs. Philadelphia Eagles football game and walking arm in arm in NYC. By 2008, they quietly said their goodbyes and moved on.

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P. Diddy

Hooking up on-and-off since 2008, the good friends turned heads when Diaz was spotted "straddling" the rap mogul during a star-studded CAA gala at Hollywood's Soho House in January 2012. In November 2014, Diddy was overheard gushing about the actress to some of his buddies. "He was at a dinner and the subject turned to Cameron dating Benji Madden. He said, 'If I could turn back time, things would be different!'" a source exclusively revealed to Us. "He was bummed, saying, 'She's the sexiest girl in the world.'"

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Paul Sculfor

Why, hello! Diaz briefly snagged the British model from 2008 to 2009. The couple were rarely photographed together, but couldn't escape lenses during a US Open tennis match in New York in September 2008. The pair cuddled up and kissed at their seats.

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Edward Norton

Not copping to it! The Charlie's Angels star was spotted getting cozy with Norton in January 2009. Despite the friendly photos that surfaced, the stars never confirmed nor denied that they dated. The following year, Diaz swore off marriage to UK Stylist magazine. "Who would want to be with the same person for 80 years?" she said. "Why not break it up a little bit?"

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Alex Rodriguez

That popcorn though! Diaz and the Yankees slugger dated from summer 2010 to fall 2011, and kept the romance going with several trips to Mexico, Miami, London, NYC, and L.A. One of their most memorable hangouts was when Diaz was caught feeding the athlete popcorn during 2011's Super Bowl in Texas. "All of a sudden, I see [Alex's] hand coming in," Diaz recalled of the funny munching-fest to Us at the time. "…I went, 'You know what? I love you too much, I'm going to give it to you. You deserve it.'"

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Benji Madden

Surprise! After years of saying she'll never get hitched, Diaz married the Good Charlotte rocker in a backyard wedding at her Beverly Hills pad in January 2015 after seven months of dating. Nicole Richie and BFF Drew Barrymore were bridesmaids and she walked down the aisle to Nat King? Cole's "Stardust." Us broke news just days earlier that the couple were engaged. "It was a beautiful, heartfelt ceremony," an insider told Us.