I have a particular interest in health, spirituality, fitness, and the mind-body connection. Older men can have sophisticated tastes; are you ready for that? Dylan Mcleod via Unsplash Public Domain. We all remember when year-old Ashley Olsen made headlines for reportedly dating year-old Bennett Miller, the director of Moneyball. And yes, I know some younger men date older women. Kyle Jones, a year-old Pittsburgh man, raised eyebrows for having a relationship with year-old great-grandmother, Marjorie McCool.