CAMERON DIAZ AND MATT DILLON – 3 YEARS

The actors met back in 1995 while filming their respective shows in Minnesota (Feeling Minnesota for Diaz and Beautiful Girls for Dillon). According to Diaz, the two didn’t start dating until January 1996 (though at the time she was tight-lipped about the identity of her “boyfriend,” who she described as “in the business”). Though Diaz and Dillon managed to keep out of the public, the few statements the former made about her S.O. were adorably endearing. Diaz told the British Guardian in 1997, “I love him incredibly.”

Cameron Diaz and Matt Dillon started dating in 1996 and were cast in the same film, there’s Something About Mary, which became one of Diaz’s most memorable roles. While they played romantic interests in the film, their relationship investments did not last in real life, and they broke up shortly after production.