When it comes to Hollywood romances, Cameron Diaz has certainly had her share of love stories—some serious, others fleeting—but all intriguing. In this post, we’ll walk you through the Complete Dating History of Cameron Diaz, in a way that’s smooth, clear, and genuinely engaging. We’ll spotlight who she dated, when, and how each relationship shaped her journey toward lasting love.
The Complete Dating History of Cameron Diaz has fascinated fans for decades. Known for her radiant smile, infectious energy, and blockbuster rom-coms, she’s also amassed an intriguing romantic timeline. From early relationships in the modelling world to high-profile star romances—and finally finding her forever partner—this overview dives into every chapter of her romantic life.
Carlos De La Torre (1990–1994)
Cameron’s first serious relationship began while she was still a model, marking the early chapter in the Complete Dating History of Cameron Diaz. in 1990, she struck up a romance with the producer, Carlos De La Torre. They lived together in West Hollywood until their split in 1994, just as her acting career was taking off.
Matt Dillon (1996–1998)
She met Matt Dillon in 1995 while filming movies in Minnesota and they began dating in early 1996. Their relationship was fairly private but affectionate—Dillon later called Diaz his “muse.” This romance became a notable chapter in the Complete Dating History of Cameron Diaz, though it ended in 1998 as their busy careers and constant travel eventually pulled them apart.
Jared Leto (1999–2003)
Following Dillon, Cameron was briefly engaged to Jared Leto. Their relationship spanned roughly three years—from around 1999 to their breakup in early 2003.
Justin Timberlake (2003–2006)
Next up was pop icon Justin Timberlake. The two dated from April 2003 until December 2006—a high-profile romance that ended after three years.
Kelly Slater (2007)
In 2007, Cameron Diaz was briefly linked to professional surfer Kelly Slater following her split from Justin Timberlake. The two were spotted spending time together, sparking speculation of a short-lived romance. However, neither Cameron nor Kelly confirmed the relationship, and it is widely regarded as a casual dating rumor rather than a serious relationship.
Tyrese Gibson, Criss Angel, Djimon Hounsou (2007)
2007 was a busy year for Cameron Diaz in the tabloids, as she was rumored to have brief flings with actor and singer Tyrese Gibson, illusionist Criss Angel, and actor Djimon Hounsou. These encounters sparked headlines, but none of the relationships were ever confirmed.
Most reports suggested that the connections were casual meetups or short-lived attractions rather than serious romances. Cameron, known for keeping her private life guarded, never publicly addressed these rumors, leaving them as part of Hollywood’s ongoing speculation about her love life.
Paul Sculfor (2008–2009)
In 2008, Cameron Diaz began dating British model Paul Sculfor, who had also been linked to Jennifer Aniston in the past. Their relationship was more serious compared to some of her rumored flings, lasting nearly a year. The two were spotted enjoying cozy dinners, vacations, and attending events together, drawing plenty of attention from the media.
Friends of the couple described their bond as affectionate and genuine, though their busy schedules often kept them apart. By mid-2009, the pair quietly ended their relationship, but it remained one of Cameron’s more stable romances of the late 2000s.
Sean ‘Diddy’ Combs (2008–2012)
From 2008 to 2012, Cameron Diaz was frequently linked to music mogul Sean “Diddy” Combs. While neither openly confirmed a serious relationship, their connection was described as an on-and-off “encounter” that stretched over several years. They were often spotted together at parties, industry events, and private getaways, fueling speculation about their romance.
Some reports suggested the two shared a playful, casual bond rather than a committed partnership. Despite the buzz, both Cameron and Diddy remained private about the nature of their relationship, leaving it one of Hollywood’s more intriguing mysteries.
Keanu Reeves (2009–2010)
Around 2009 and 2010, Cameron Diaz was rumored to be romantically linked to actor Keanu Reeves. The speculation began after the two were spotted dining together and attending a few events in Los Angeles, sparking curiosity among fans and the media. Their outings suggested a close friendship that may have hinted at something more, though neither Cameron nor Keanu ever confirmed a relationship.
Reports at the time described their connection as casual and friendly rather than a serious romance. While the rumors eventually faded, the pairing intrigued fans who admired both stars’ down-to-earth personalities and Hollywood status.
Alex Rodriguez (2010–2011)
In 2010, Cameron Diaz began dating New York Yankees star Alex Rodriguez, marking one of her most high-profile relationships. The couple quickly became a media favorite, often photographed together at sporting events, vacations, and red-carpet appearances. Their romance seemed serious, with Cameron even joining Alex at family gatherings and supporting him during his baseball games.
Despite the public attention, both maintained that they valued their independence and careers. By the summer of 2011, the relationship came to an end, though reports suggested they parted amicably. Their time together remains one of Cameron’s most talked-about romances of the early 2010s.
Elon Musk (2013)
In 2013, Cameron Diaz was briefly linked to tech billionaire Elon Musk, sparking curiosity due to their vastly different worlds. Reports claimed that Cameron had visited Elon at Tesla’s design studio and that the two shared a mutual admiration for innovation and business. While the rumors gained attention, there was never any confirmation of a serious relationship.
Sources close to both suggested that their connection was casual and likely more professional or friendly than romantic. Despite the short-lived speculation, the story highlighted Cameron’s ability to surprise fans with unexpected links outside of Hollywood.
Why This Romantic Journey Matters
Cameron Diaz’s dating history highlights her personal growth and evolution over the years. From youthful romances and Hollywood flings, she matured into someone who values depth, partnership, and family. Her relationship with Benji Madden, in particular, reflects mutual respect, support, and intentional decision-making—traits that stand out in celebrity relationships.
How Cameron Diaz Balanced Love and Career
Throughout her career, Cameron was one of the most in-demand actresses in Hollywood. Balancing blockbuster filming schedules with relationships wasn’t easy, and many of her breakups stemmed from career pressures. Still, each romance helped her grow both personally and professionally.
Public Attention on Her Relationships
As a major star, Cameron’s love life was often headline news. From paparazzi photos to tabloid rumors, her dating life was never private. Despite the attention, she handled the spotlight gracefully, often avoiding unnecessary drama.
Cameron Diaz on Staying Single Between Relationships
In several interviews, Cameron admitted she enjoyed her single years. They gave her space to focus on herself, her friendships, and her career. She often highlighted the importance of self-love before committing to a serious relationship.
Cameron Diaz Today: Focused on Family and Happiness
Now semi-retired from acting, Cameron spends most of her time with her family and close friends. She has shifted her focus to wellness, business ventures, and raising her children. Her dating history may fascinate fans, but today her story is about peace, love, and fulfillment.
Becoming a Mother Later in Life
Cameron embraced motherhood at 47, proving that family dreams can come true at any stage of life. With her daughter Raddix and son Cardinal, she has openly expressed how much joy family has brought her. It’s a role she fully cherishes today.
Cameron Diaz’s Views on Marriage Before Benji
Interestingly, Cameron once said she didn’t believe she was “cut out for marriage.” For years, she preferred independence and freedom. Her decision to marry Benji showed just how special their bond truly was.
Why Her Relationship with Benji Madden Stood Out
Unlike previous romances, Cameron’s connection with Benji was immediate and lasting. Their shared values, family focus, and genuine friendship became the foundation of their marriage. Fans noticed this difference, often calling their love story one of Hollywood’s sweetest.
Cameron Diaz’s Chemistry with Co-Stars
Many of Cameron’s rumored romances began on film sets. Her natural charm and chemistry with co-stars like Tom Cruise, Matt Dillon and Justin Timberlake made headlines. Fans often blurred the line between on-screen romance and real-life connections.
From modeling beginnings to finding true love, Cameron Diaz’s dating history is a testament to growth, reflection, and finally discovering a partner who complements and uplifts her.
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