Demi Lovato and Wilmer Valderrama (With a 12-year age gap)
Even though their relationship is over, Valderrama appears to have a thing for younger women. His preferences have gotten a lot of press in the past, particularly during his six-year marriage to Demi Lovato.
Despite their 12-year age gap, the pair seemed to be able to overcome their issues. The two eventually broke up and moved on with their lives. Wilmer is now dating Amanda Pacheco and has a daughter with her.