'The thought of being a widow for plus years terrifies me' Just the thought of seeing someone else makes me feel sick and anxious. Dating an older man isn't about the age -- it's about the lifestyle. Even though this guy and I were 25 years apart, we had a lot in common. been married to someone for more than a decade who is 20 years older than her. If You're Thinking Of Dating Someone Younger, You Need To Read This First For example, when a rapper in his late 20s dates a year-old.