Dear Say More: Why are relationships between older women and younger men viewed as strange or socially unacceptable, while older men and younger women dating appears to be socially acceptable? I am 71 years old and enjoy the company of a 49-year-old man. When we are out, he is often asked if I am his mother, although we look nothing alike. Some of his friends have told him that it seems weird to be with a woman not only who is older, but who would not be considered a “GILF” or “MILF. ” I am a grandmother and look like one. haha lol.