#16: Oliver Whitcomb: The Beginning (1999-2002)

Demi Moore’s relationship with martial arts instructor Oliver Whitcomb marked a departure from her high-profile Hollywood romances. They began dating in 1999, following her divorce from Bruce Willis. Oliver, who lived a private life, offered Demi stability and a connection outside the entertainment industry.

She had stepped away from acting to focus on raising her three daughters, and their relationship was built on shared values of wellness and self-improvement. Despite their low-key romance, they were often hiking and practicing martial arts together.