Before Cameron Diaz happily settled down with Good Charlotte's Benji Madden in 2015, this blonde beauty was known for dating several of Hollywood's most handsome men. From fellow actors to a pop star in a boy band, and even professional athletes, Diaz's dating history is quite impressive.Since her breakout role in The Mask, she's gone on to date other actors like Matt Dillon and Jared Leto, though a rumored romance with Jim Carrey has never been substantiated.The actress has even dated a couple of athletes from a major baseball star to a surfer.Updated September 6th, 2022: Cameron Diaz may not consider all her exes frogs, but she finally found long-term love with Benji Madden, and the two welcomed a daughter together in 2020. Enjoy this walk down memory lane, recapping many of Diaz's past relationships with famous men.
10 Carlos De La Torre
Before Cameron Diaz would land her breakout role in The Mask, opposite Jim Carey, she was dating video producer Carols De Le Torre after meeting him for a photo shoot for LA Gear in 1990, according to PopSugar.
At the time, Diaz was infatuated with Torre, confessing to People. "I spent an entire day trying to meet him to talk to me." The two had a pretty lengthy relationship, dating for four years, but split in 1994 when she hit it big in Hollywood.
9 Matt Dillon
Cameron Diaz and Matt Dillon dated back in 1995 and were cast in the same movie — There's Something About Mary, which would become one of Diaz's most memorable roles.
While the two played love interests in the film, their romance wouldn't last in real life, and they broke up right after filming the comedy.
At the time of their split, Dillon revealed to People, "I was dissatisfied with where I was as a man, with my relationships, with my career ... I thought my career was who I was. It wasn't until later that I discovered I was more than that ... Cameron was a muse for me."
8 Jared Leto
Fans may not remember that Cameron Diaz once dated 30 Seconds to Mars rockstar Jared Leto, but the two did have a brief romance from 1999 to 2003.
They were even rumored to have gotten engaged at one point but eventually, the celeb couple called it quits, and it looked as though Leto wasn't ready to settle down.
After the two split, Leto was linked to many other Hollywood women, including Scarlett Johansson, Paris Hilton, Miley Cyrus, and Angelina Jolie.
In an interview with Rolling Stone, the singer reflected on why he hasn't been able to commit, sharing, "I'm too obsessed with my own creative ambitions and my own goals."
7 Justin Timberlake
Cameron Diaz and Justin Timberlake had a highly publicized romance when they began dating in 2003, after meeting at the Nickelodeon Kids' Choice Awards, according to PopSugar. The pair went everywhere together, and Diaz even joined Timberlake on tour at one point.
However, it would all come to an end in 2007, when the two both released a statement that read, "We have, in fact, ended our romantic relationship, and have done so mutually and as friends, with continued love and respect for one another."
Even after their split, they did end up working on two movies together — Shrek 3 and Bad Teacher.
6 Criss Angel
Diaz dating magician and illusionist Criss Angel seemed out of the blue, but they were spotted hanging out several times in Las Vegas in 2007.
While Angel denied romance rumors, he did give the actress a shout-out during one of his shows, saying, "I'd like to dedicate this to my girl Trouble aka Cameron. I love you, baby."
Diaz and Criss Angel continually denied their relationship, but that same month he shouted Diaz out, his estranged wife sued the magician, stating he had an affair with Diaz.
5 Sean "Diddy" Combs
According to Us Weekly, Cameron Diaz and rapper Sean "Diddy" Combs had a romantic relationship from 2008 to 2012, with the Bad Boy mogul admitting that the actress was "the one that got away."
During a night out, after the subject of Diaz dating her now-husband, Benji Madden arose, the rapper was revealed to have said, "If I could turn back time, things would be different!"
4 Kelly Slater
People began to speculate that Cameron Diaz and pro-surfer Kelly Slater were an item in 2007 when the actress was spotted in Hawaii surfing with Slater, according to WhosDatedWho. It was also rumored that she flew to Hawaii after she broke up with Justin Timberlake with Slater helping her get through the difficult time.
However, Slater told People, that the two were "just friends," even though they were seen on numerous occasions surfing, playing golf, and grabbing dinner.
3 Paul Sculfor
One of Cameron Diaz's short-lived romances was with British model Paul Sculfor, whom she dated for a year in 2008 before ending things in 2009. Several photos showed the two cuddling and kissing.
It was reported that Sculfor "dumped" the blonde beauty because she refused to move to the U.K.
2 Alex Rodriguez
While Cameron's relationship with former New York Yankees player Alex Rodriguez would also be brief, (the two dated for just a year between 2010-2011) it was one of the actress's most highly profiled romances.
It appeared that the stars were having a fantastic time with one another, especially during the summer of 2010, but it all ended rather quickly.
"I don't like talking about my relationships, but I will tell you about CD. She's probably one of the greatest human beings I've ever met, and just an amazing light," Rodriguez revealed after he had broken up with the actress.
1 Benji Madden
It looked like Cameron Diaz always had a thing for the rocker type after she began dating Good Charlotte's Benji Madden in 2014. The two were married in 2015 and welcomed a daughter named Raddix in 2020.