#22: Sean Friday: The Beginning (2013-2014)

Demi Moore rebounded with musician Sean Friday in late 2013, following her painful divorce from Ashton Kutcher. The Dead Sara drummer was nearly 24 years younger than Demi, continuing her pattern of dating younger men.

They were first spotted vacationing in Mexico, where their flirtation became public. After years of emotional turmoil, Sean’s carefree, rocker lifestyle seemed to bring Demi joy. Friends noted she appeared relaxed and happy in his company, embracing a spontaneous and fun-filled romance.