Cameron Diaz’s first high-profile romance was with Matt Dillon. The pair met while they were each filming separate movies in Minnesota in 1995 and would later co-star in “There’s Something About Mary” before splitting in 1998. Dillon later told Parade magazine (via Hollywood.com), “I fell in love. 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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Diaz dated Edward Norton briefly in February 1999, with People reporting a lot of PDA at a Super Bowl party.
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Diaz began quietly dating Jared Leto in winter 1999. They were together for four years before splitting in 2003.
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British singer Robbie Williams harbored a longtime crush on Diaz. The pair hooked up for a go-karting date in Berlin in 2003, but based on his comments later, it didn’t end well. He told The Sunday Mirror (via Glamour UK), “She looks a bit like Zippy. Crush is over. I can get on with the rest of my life.”
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Diaz and Justin Timberlake got together after she presented him with Best Burp at the Nickelodeon Kids’ Choice Awards in May 2003. Diaz was 30 and Timberlake 22 at the time, which got tongues wagging. Diaz shrugged the chatter off, telling W magazine in 2004: “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.” Diaz and Timberlake remain on good terms, co-starring in 2011’s “Bad Teacher.”
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In January 2007, Diaz was spotted hitting the waves (and maybe a few other things) with surfer Kelly Slater in Hawaii.
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People reports Diaz was spotted kissing and dirty dancing with Djimon Hounsou in February 2007.
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Reports say Diaz hooked up with Tyrese Gibson in March 2007. A spy dished, “They made out right in front of me on the dance floor!”
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Witnesses told People that Diaz got cozy with Criss Angel in May 2007 in Las Vegas over dinner and a show. “They were snuggling with each other and he was making her laugh,” a spy revealed. “They seemed really happy.”
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While Diaz was careful never to be photographed with John Mayer, People reports the pair had a fling in August 2007.
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Though their reps denied it, E! News reports Diaz dated Bradley Cooper in August 2007.
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Diaz dated model Paul Sculfor from June 2008 to May 2009, reportedly splitting due to long distance. Sculfor is a UK native, while Diaz loves Los Angeles and spends time in New York.
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Diaz was spotted on a date with Maroon 5 frontman Adam Levine in May 2009. A source told X17 (via Digital Spy), “Cameron was laughing at all of Adam’s jokes and they seemed like such a perfect match. They were even dressed alike!”
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After starring in “Feeling Minnesota” together in 1996, Diaz and Keanu Reeves hooked up in August 2009, the UK’s Sun reports.
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Though they never spoke of their romance at the time (roughly from May 2010 to September 2011), who could forget Diaz feeding Alex Rodriguez popcorn at the 2011 Super Bowl? Rodriguez only had kind words about Diaz later on, though, telling “The Insider,” “I don’t like talking about my relationships, but I will tell you about CD: She’s probably one of the greatest human beings I’ve ever met, and just an amazing light.”
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Diaz hooked up with Sean “Diddy” Combs in January 2012 at a CAA gala, but it wasn’t the first time: Us Weekly reports the pair had been hooking up on and off since 2008.
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Tesla Motors CEO Elon Musk had a fling with Diaz in March 2013.
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After a 7-month romance, Diaz is rumored to be engaged to Good Charlotte rocker Benji Madden. “Everyone thinks it’s wild but are so happy for them,” a source told Us Weekly. “Benji always tends to fall in love easily, but this time it’s for real and he landed a great girl. They obviously both make each other incredibly happy and there’s nothing better than that.”
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