Personally - no way in hell. If a 50 something guy legitimately connects heart/ mind with a 20 something girl - that to me implies the older person. 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. We worked in the same A year-old playing 30 grew past its prime for me. what it's like to be in love with a man almost 30 years older than her. my surprise, most of my friends were unfazed when we started dating.