Ashton Kutcher, 42 and Demi Moore, 57—16 year difference

Demi Moore was born on November 11, 1962, and Ashton Kutcher was born on February 7, 1978, 15 years younger than Moore. Their relationship definitely raised more than a few eyebrows, and while the age difference was certainly a factor, it really had more to do with the fact that they were both high-profile celebrities. They met in 2003 and tied the knot in 2005. Six years after their incredibly high-profile marriage, the couple split, and rumors began swirling that it was, to a huge degree, because of some third party.

In Moore’s memoir, she revealed that infertility issues, their semi-open relationship, and Kutcher’s infidelity was what ultimately did them in. Moore has been married three times. The first marriage was to Freddy Moore, and it was finalized in 1985. Her second husband was Bruce Willis, and the couple ended in divorce in 2000.