Most men in their 50s (including myself) have older children who are either in high school, college, or out in the working world. Because our. hese days more than ever, single people in their 50s — both men and women — feel free to date a wide range of age groups. Still one has to wonder: Is hooking. The baggage is not so much Louis Vuitton, more like a supermarket plastic bag with holes in it. The more guys you meet, the more depressing it.