Cameron Diaz's Famous Men

Justin Timberlake, Jared Leto and the other guys who came before she wed Benji Madden
By Alison Schwartz
Updated January 01, 2015 09:00 PM

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CARLOS DE LA TORRE

Credit: The LIFE Picture Collection/Getty

While shooting an ad for LA Gear in 1990, Diaz fell for the producer, telling PEOPLE, "I spent the entire day trying to get him to talk to me." The couple went on to share a two-bedroom apartment in West Hollywood within a year of dating, but by 1994, they'd moved on.

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MATT DILLON

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The actress was shooting a movie in Minnesota in 1995 when she met Dillon, who was also filming there. "I love him incredibly," she gushed in 1997, not long before they quietly called it quits in 1998.

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JARED LETO

Credit: Charbonneau/Beimages

Before he had an Oscar and before he had a man bun, he had Diaz. Their low-key relationship led to rumors of wedding bells when the actress was spotted wearing a $15,000 ring to the 2003 Golden Globe Awards. But ultimately, there's no trip down the aisle for the couple, who broke up in 2003 after dating for four years.

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JUSTIN TIMBERLAKE

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Timberlake was 22 when he started up with Diaz, then 30. "It's not like this is the first time in the history of human relationships that people were drawn to one another because of who they are, not what age they are," the actress later said. And when their nearly four-year relationship ended in 2007, they both kept it professional, reuniting to promote their animated film Shrek the Third, and later joining forces again for 2011's Bad Teacher.

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BRADLEY COOPER

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Central Park strolls, Saturday Night Live afterparties, New York Giants games: Diaz and Cooper were spotted all over N.Y.C. in 2007 – but were they or weren't they? "I think she's great," the actor told PEOPLE. "We're good friends."

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GERARD BUTLER

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Spring fling? Shortly after being romantically linked to Dancing with the Stars champ Cheryl Burke, Butler was spotted cuddling and partying with Diaz around L.A. in 2008.

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PAUL SCULFOR

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"I'm in love with love," Diaz declared in 2008. Although she said she was keeping her options open, she soon paired off with the model, staying with him until 2009.

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ALEX RODRIGUEZ

Credit: Ramey

Speaking of playing the field: Diaz was spotted cozying up to the New York Yankee in Boston when the baseball star was in town for a 2010 game. After spending the summer together in New York, they broke up in the fall of 2011. "I have a lot of love for Cameron," Rodriguez told PEOPLE. "We'll always be friends."

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BENJI MADDEN

Credit: FameFlynet

He's the one! After months of dodging engagement rumors, a friend of the rocker confirmed the December 2014 proposal, which came after seven months of dating. "You have to find someone else in the same place as you are," Diaz has said. "Timing is everything." Weeks later, on Jan. 5, 2015, the couple made it official, marrying in Beverly Hills.

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By Alison Schwartz