Cameron Diaz's Love Life in Photos

From Matt Dillon to Justin Timberlake, the actress has had quite the string of high-profile relationships -- but still hasn't found the one

When it comes to relationships, Cameron Diaz is basically the female George Clooney.

She likes to talk about how marriage is a dying institution; she's not interested in having kids; and as far as the public knows, she's never even been engaged. Like Clooney, she's also obsessively private about her love life.

But she's certainly not lonely! Over the years, Diaz has been in long-term relationships with many desirable men; most recently, she's rumored to be spending time with Jason Segel. In celebration of her 41st birthday, we look back on some of the actress' big romances.

Matt Dillon (Dated September 1996 - September 1998)

Cameron Diaz Matt Dillon

Dave Benett/Getty Images


Relationship Highlight: Diaz and Dillon met while filming two different movies in Minnesota; three years later, they finally shared a screen in the hit comedy There's Something About Mary. "Three years ago, the thought of working with my girlfriend...would have been horrifying," Dillon told W magazine in 1998.

How it ended: Ironically, the couple split up not long after making their romantic comedy. When Diaz's wedding-gone-wrong movie Very Bad Things came out in November, she joked, "I got out all my wedding aggressions in the film." Nearly 10 years later, Dillon recalled that Diaz was his first "deep emotional relationship." "It's a very powerful thing when you feel that way about somebody," he told Parade. "Cameron was a muse for me."

Jared Leto (Dated March 1999 - April 2003)

Cameron Diaz Jared Leto

Jeff Kravitz/FilmMagic

Relationship Highlight: After dating the My So Called Life actor for four years, Diaz showed up at the 2003 Golden Globes with a giant diamond on her ring finger. (Leto didn't show up the event, but he joined her at the after parties.) Were they engaged? We may never know!

How it ended: The couple kept their relationship intensely private, and they same went for their break-up. Nevertheless, the rumor mill had plenty of theories. The top three: Jared was more interested in his band 30 Seconds to Mars than he was in Cameron; Cameron found out that Jared was cheating on her; and Jared was jealous of Cameron's success as an actress.

Justin Timberlake (Dated April 2003 - January 2007)

Cameron Diaz Justin Timberlake

Kevin Mazur/WireImage

Relationship Highlight: This playful couple met at the 2003 Kids Choice Awards, when Diaz, then 30, presented Timberlake, then 22, with the "Best Burp" award. (She was the previous year's winner.) The press made a big deal of their age difference, but the couple did not. "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 told W in 2004.

How it ended: There were rumors of trouble throughout their relationship, and both stars sued tabloids for reporting that they were cheating (with model Lucy Clarkson and producer Shane Nickerson, respectively). US Weekly reported that the final straw was a flirtation between Timberlake and Scarlett Johansson. Nonetheless, the couple insisted that they split on good terms -- and proved it when they co-starred in the sexy 2011 comedy Bad Teacher.

Paul Sculfor (Dated June 2008 - May 2009)

Cameron Diaz Paul Sculfor

Chris McGrath/Getty Images

Relationship Highlight: A year after breaking up with Timberlake, and following a rumored fling with John Mayer, Diaz began dating Jennifer Aniston's ex-boyfriend Paul Sculfor. In September 2008, Cameron and the male model attended the U.S. Open together, but really didn't appear to be watching the game!

How it ended: The couple reportedly broke up because the distance between her Los Angeles and his native England became too much. "I love being single," Sculfor told More in 2009. "It was my choice to be single. It's great to be on my own - you don't want to be tied down, do you?"

Alex Rodriguez (Dated May 2010 - September 2011)

Cameron Diaz Alex Rodriguez

George Pimentel/Getty Images for Creative Artists Agency

Relationship Highlight: Diaz never talked about her romance with the Yankees slugger, but one picture was worth a thousand words: a shot of Cameron feeding A-Rod popcorn during the 2011 Super Bowl.

How it ended: The actress and athlete reportedly ended their relationship to focus on their professional lives. "She's very busy with her career. And he's had injuries and wants to focus on his game," a source told US Weekly. In 2012, Rodriguez broke his silence and gushed about his ex to The Insider. "She's probably one of the greatest human beings I've ever met, and just an amazing light," said the ballplayer. 
Like this? Want more?
preview
Connect with Us
Follow Our Pins

Yummy recipes, DIY projects, home decor, fashion and more curated by iVillage staffers.

Follow Our Tweets

The very dirty truth about fashion internships... DUN DUN @srslytheshow http://t.co/wfewf

On Instagram

Behind-the-scenes pics from iVillage.

Best of the Web