Ashton Kutcher Had A Crush On This Stunning Former Co-Star

The early 2000s were the height of fame for one Ashton Kutcher. Leaping straight from "That '70s Show" to "Punk'd" saw the comedic actor turned host become a household name during the peak of the celebrity obsession era. Of course, Kutcher has had his fair share of controversial moments, many of which surround his bravado around women. During a rowdy 2003 interview with Rolling Stone, the "Dude, Where's My Car?" star admitted to having a crush on fellow actor Cameron Diaz. However, it seems that Kutcher might have manifested his own meet-cute as the two were destined to be co-stars just five years later. 

In 2008, the movie "What Happens In Vegas," starring Kutcher and Diaz in the lead roles, came out to middling reviews. Though both were at a successful point in their careers, it seems the duo didn't quite have the requisite chemistry to pull off a raunchy rom-com. Though the film was a flop, they had fun with each other on set. In fact, Kutcher only had glowing things to say of his co-star and crush. "There really isn't anyone who does comedy as well or as successfully as Cameron," he gushed to Variety at the time. 

Although the actor probably wanted to ask the "Charlie's Angels" star out on a date, there was a sound reason for his uncharacteristic avoidance. "I wouldn't recommend dating co-workers," Kutcher advised Rolling Stone. "It's not smart." While it seems that he kept things smart with Diaz, the "Jobs" star does have a history of blurring the lines between work and pleasure, particularly considering what Kutcher's exes have said about him.

Even though he didn't end up becoming romantically involved with Cameron Diaz, Ashton Kutcher has always had a way with women, including those he's starred alongside. Kutcher was once in a relationship with January Jones and he was also famously married to fellow actor Demi Moore. But the "That '70s Show" star broke his own rule when Kutcher dated his "Just Married" co-star Brittany Murphy. However, their romance was short-lived, ending just a few months after the movie was released in theaters.

He and current wife Mila Kunis also started out as co-stars, officially breaking Kutcher's own rules yet again. To make matters even more intimate, Kunis and Kutcher have both kissed A-list celeb Natalie Portman onscreen. Despite their reportedly healthy marriage, which has been going strong for years, Kutcher's own crushing on co-workers might have led to him projecting some fears onto Kunis' cozy relationship with co-star Josh O'Connor. 

For her part, Diaz has been happily married to Benji Madden of Good Charlotte since 2015. The celebrity couple has two children, daughter Raddix, who was born in December 2019, and son Cardinal, whom they welcomed in March 2024. By consistently staying out of the limelight, the Madden-Diaz household appears to be thriving. Considering all the weird things we know about Kutcher and Kunis, the couple could do well to take some notes.