As the actress welcomes her third child with husband Benji Madden, we look back at the relationships that came before she found lasting love.

<a href="https://www.lofficielusa.com/fashion/cameron-diaz-best-movie-fashion-moments">Cameron Diaz</a> and Benji Madden welcomed their third child, a son named Nautas, this week, marking another milestone in a decade-long marriage that appears to be exactly what Diaz was looking for all along. It's a partnership built on genuine compatibility rather than tabloid spectacle, a notable shift from the intense media scrutiny that accompanied her earlier relationships.&nbsp;
Before marrying Madden in 2015, Diaz navigated several serious relationships over two decades, each reflecting different chapters in both her personal life and Hollywood's evolving relationship with celebrity privacy. Below, take a look at those partnerships and explore how they led to where she is now.

<h2 class="text-text-100 mt-3 -mb-1 text-[1.125rem] font-bold" style="text-align: center;">Carlos de la Torre (1990&ndash;1994)</h2>

Getty Images.

Diaz's first serious relationship was with video producer Carlos de la Torre, whom she met in Japan while filming an LA Gear commercial. This was before The Mask launched her film career, when she was working primarily as a model. The four-year relationship ended in 1994 as her professional life began to shift: a natural transition as both their careers evolved in different directions.

<h2 class="text-text-100 mt-3 -mb-1 text-[1.125rem] font-bold" style="text-align: center;">Matt Dillon (1996&ndash;1998)</h2>

Diaz and Matt Dillon were together from January 1996 to September 1998, a relationship that coincided with There's Something About Mary, the film that established Diaz as a leading actress. Dillon later spoke warmly of their time together, describing Diaz as his "<a href="https://www.instyle.com/celebrity/tbt-cameron-diaz-matt-dillon-relationship?utm_campaign=instyle_instyle&amp;utm_content=bestofevergreen&amp;utm_medium=social&amp;utm_source=twitter.com&amp;utm_term=60df274569c7e100014810f7">muse</a>," while co-star Lin Shaye remembered them as affectionate in a really gentle way" on set. It was the kind of relationship that worked until it didn't, as both were navigating rapid career growth while trying to maintain something private in an increasingly public industry.

<h2 class="text-text-100 mt-3 -mb-1 text-[1.125rem] font-bold" style="text-align: center;">Jared Leto (1999&ndash;2003)</h2>

Diaz and actor-musician <a href="https://www.lofficielusa.com/film-tv/12-most-iconic-jared-leto-roles-movies-tv-joker">Jared Leto</a> were together (and reportedly unofficially engaged) between 1999 and 2003. The four-year relationship was notably low-profile for two people of their fame level, a testament to their commitment to keeping their personal life separate from their professional personas. It ended amicably, as these things sometimes do when careers demand different things from different people.

<h2 class="text-text-100 mt-3 -mb-1 text-[1.125rem] font-bold">Justin Timberlake (2003&ndash;2006)</h2>

Diaz's relationship with <a href="https://www.lofficielusa.com/pop-culture/justin-timberlake-apologizes-to-britney-spears-janet-jackson-instagram">Justin Timberlake</a> lasted from April 2003 to December 2006, making it one of the most documented celebrity pairings of the mid-2000s. The couple met at the Nickelodeon Kids' Choice Awards and quickly became serious, with Diaz supporting Timberlake by joining him on tour. Despite intense media attention, they maintained respect for each other throughout. When they ended things in 2007, they released a joint statement emphasizing their continued love and respect for one another, and even worked together professionally afterward on Shrek the Third and Bad Teacher.

<h2 class="text-text-100 mt-3 -mb-1 text-[1.125rem] font-bold">Paul Sculfor (2008&ndash;2009)</h2>

Diaz dated British model Paul Sculfor for nearly a year between 2008 and 2009. The relationship was more private than her previous ones, reflecting perhaps a desire for something outside the Hollywood ecosystem. It ended due to logistical challenges, a common issue for people with demanding international careers.&nbsp;<a href="https://www.thethings.com/all-of-the-famous-men-cameron-diaz-has-dated/" target="_blank" class="group/tag relative h-[18px] rounded-full inline-flex items-center overflow-hidden -translate-y-px cursor-pointer" rel="noopener"></a>

<h2 class="text-text-100 mt-3 -mb-1 text-[1.125rem] font-bold" style="text-align: center;">Alex Rodriguez (2010&ndash;2011)</h2>

From May 2010 to September 2011, Diaz was in a relationship with former New York Yankees player Alex Rodriguez. Rodriguez spoke highly of Diaz after their split, calling her "one of the greatest human beings" he'd ever met and "an amazing light". Their year together demonstrated mutual admiration even when romantic compatibility didn't last. <a href="https://en.wikipedia.org/wiki/Cameron_Diaz" target="_blank" class="group/tag relative h-[18px] rounded-full inline-flex items-center overflow-hidden -translate-y-px cursor-pointer" rel="noopener"></a>

<h2 class="text-text-100 mt-3 -mb-1 text-[1.125rem] font-bold" style="text-align: center;">Benji Madden (2014&ndash;Present)</h2>

Cameron Diaz and Benji Madden. Getty Images.

Diaz married Good Charlotte guitarist Benji Madden on Jan. 5, 2015, ten months after being introduced by Nicole Richie, who is married to Madden's twin brother Joel. The seven-month courtship was notably swift, and the private ceremony signaled a different approach to how Diaz wanted to live her life going forward.
The couple now has three children&mdash;daughter Raddix born in 2019, son Cardinal born in 2024, and son Nautas born May 2026&mdash;all of whom were welcomed with minimal publicity. Diaz has said that her marriage to Madden showed her "what real love is" and "what real commitment and devotion is"&mdash;not a dismissal of what came before, but an acknowledgment that sometimes it takes time to find the right fit," per <a href="https://www.yahoo.com/lifestyle/matt-dillon-said-cameron-diaz-195407946.html" target="_blank" class="group/tag relative h-[18px] rounded-full inline-flex items-center overflow-hidden -translate-y-px cursor-pointer" rel="noopener">Yahoo.</a>
What her dating history really illustrates isn't a pattern of failed relationships but rather a series of genuine connections that ultimately led somewhere better. Each partnership taught her something, and the fact that she eventually found someone who made her want to step back from Hollywood entirely speaks to knowing yourself well enough to recognize the right thing when it arrives.

Cameron Diaz's Complete Dating History

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