Cameron Diaz's Famous Men
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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.
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.
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.
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."
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.