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The things to consider looking at when dating an older man are: In the last couple of decades, people have had more flexibility around their career options and increased choice has become the norm.The older man might feel he has an improved “stud-like” status and the woman may feel she has established herself at a higher level.OK, she might be classed as a gold digger, but it’s an accepted and well-trodden path. In my dating life, prior to marrying my husband, I was always attracted to and dated older men.When you are in your 20s, a guy in his 40s doesn’t seem that old.However, when you’re in your 30s dating someone in their 50s, situations do arise (and certain things don’t rise to the occasion).