30-something man explains his views on dating after his 20s. What you are about to read is an analysis from a 30-something single guy on dating in your 20s vs 30s. Dating ain’t easy, no matter how much fun it can be, or not be. “To be, or not to be” is the question that Shakespeare’s Hamlet asked of himself about life; which only now as a man in my mid-to-late-thirties is better referenced in the dating world.. To be single, or not to be single. To go on “this” date, or not go on that date. To make a second date happen, or to not make a second date happen. To be the single man in your neighborhood, your workplace, your house of worship, your circle of friends that let you be you, that support you, or are weary of you, those that feel sorry for you, (from their own perspective) and those that are jealous of you because they still see the blue war paint as you stand as a symbol of their own long-lost days of independence while in their mind you scr