A handful of Hollywood’s brightest stars have the most complicated love lives and Cameron Diaz’s love life is no exception. Before her eternity with rocker Benji Madden, the actress had a string of celebrity romances that ranged from deeply personal to tabloid-obsessed, leaving their own series of marks on her journey.
From secret romances to very public splits, Diaz’s personal life was as tabloid-buzz-worthy as her box office smash films. But whatever the twists and turns of her romance, she kept her independence and never let a romance control who she was and doinks. How the experiences shaped the woman who, at 42, finally wed the one.
Here’s a behind-the-scenes look at the romances, epiphanies, and lessons that took Cameron Diaz from being a 21-year-old bride-to-be to wife and mother who says she’s never been loved in this way before.
1. The Matt Dillon Years: A Subtle but Passionate Connection
In 1996, Cameron Diaz began dating actor Matt Dillon, keeping their romance firmly under wraps. They were both newbies, and while they occasionally applauded each other’s work ethic, they kept the red carpet at bay. Diaz once told *The Guardian*, “I love him incredibly,” and referred to him as “one of a kind.”.
They were together until 1998, when Dillon told *Rolling Stone*, “I fell in love. It’s a very powerful thing when you feel that way about somebody. Cameron was a muse for me.” The breakup, which Diaz attributed partly to the stress of being apart, was her first serious emotional relationship and first publicized breakup.
2. Jared Leto: Hollywood’s Most Photogenic, Least Photographed Couple
By 1999, Diaz was also said to be dating Jared Leto, the new star of *My So-Called Life*. Though they were one of the hottest couples of the decade, they managed to keep the romance entirely hidden. They never walked the red carpet together, and whispers of an engagement were never confirmed.
Diaz has told *The Mirror*, “I don’t want to discuss him. Just understand that I love him more than anything.” The couple split in 2003 after nearly four years together, with stories suggesting Leto’s missing from her film sets contributed. This was a clandestine relationship, although one that also saw Diaz initially resistant to the idea that marriage was the key to happiness.
3. Justin Timberlake: Passion, Paparazzi, and Pain
When Diaz and Justin Timberlake met for the first time at the 2003 Nickelodeon Kids’ Choice Awards, sparks flew. Their four-year romance was similarly in the public eye, with Diaz going on tour with Timberlake and him calling on her at work. By 2006, however, rumors of cheating were rampant, fueled by accusations from Playboy Bunny Zoe Gregory and Timberlake’s own admission in his memoir *Hindsight* that he flirted with Jessica Biel within weeks of the break-up.
Despite the meltdown, Diaz got along famously with Timberlake, even sharing the big screen with him in *Bad Teacher* later. She told *Us Weekly*, “Justin and I always had a good laugh together.” The romance, however, trumpeted her so-called “commitment-phobe” nature at the time.
4. Alex Rodriguez: A Short but Shimmering Affair
Diaz dated former New York Yankees legend Alex Rodriguez in 2010. Their romance was undeniable fans remember still her hand-feeding him popcorn at the Super Bowl. The romance didn’t work out, though, after one year.
Following their breakup, Rodriguez raved about her to *People*: “She’s likely one of the best human beings I’ve ever met and just a wonderful light. I have lots of love for Cameron. We’ll always be friends.” It was one of few examples of a Hollywood romance that didn’t end with bad feelings.
5. The 21-Year-Old Marriage Dream That Never Was
In a throwback interview, Diaz admitted she dreamed of being married with two kids at 21. “But then my career was starting, and there were still so many things that I wanted to do,” she explained.
Her first loves were lessons that life does not always unfold in the sequence created in teen years. Instead, Diaz stayed focused on her independence, developing her career and personal growth before settling into domestic life.
6. Getting to Know Benji Madden: Love at First Real Sight
Even though they’d been in the same social circle, Benji Madden and Diaz had not yet met until she hosted a dinner party in May of 2014. “Joel said, ‘Hey, can my brother come over?’ And then [Benji] came in the door and I was like you! You!” Diaz explained on the *Anna Faris Is Unqualified* podcast.
Seven months later, they were engaged; a month later than that, married. Diaz later told *Harper’s Bazaar*, “I didn’t think I’d do it, and I don’t know if I would have done it if I hadn’t fallen in love with my husband. It was a shock.”
7. Creating a Life Together: Marriage, Parenting, and Partnership
Since their 2015 wedding, Diaz and Madden have welcomed two children daughter Raddix in 2019 and son Cardinal in 2024. Diaz often credits Madden with teaching her what it means to be an equal partner. “I’ve never had anyone who supported me so much and gave me so much courage to be myself,” she said at a Goop panel.
Madden’s public acknowledgements of Diaz are equally genuine. Writing on their 10th anniversary, he stated on Instagram, “Never perfect, always real always reliable. Every day getting to have my best friend with me… what a beautiful life.” In this chapter, for Diaz, it is all stability, respect for one another, and the kind of love she claims she never knew before.
Cameron Diaz’s dating history is more than a roll call of household faces; it’s a story of growing up, self-awareness, and waiting for the correct kind of love. From clandestine encounters to celebrity gossip-sheet scandals, every relationship was a learning experience, and one that finally resulted in her settling down in marriage as her greatest gift. In Hollywood, where love is nothing more than a myth, Diaz’s experience proves that sometimes the best relationships are formed when you have lived long enough to know exactly what you want.
