How Does A Boy Ask For A Date?

At what age a boy dates depends very much on the boy himself. And again physical size bears no relation to emotional readiness. Anywhere from fourteen on a boy may be ready to leave the teasing group of boys and go on his first date. His family should be well prepared for the metamorphosis that will occur.
The first sign, of course, is cleanliness. He will suddenly begin bathing without reminders, lengthily combing his hair before setting out for school instead of merely running the comb—or more likely, his fingers—through it [stress mine-AH]. Suddenly his shoes will be shined to a glassy polish, and he will stop biting his fingernails. He will require two or three times his usual number of clean shirts, and he will take an unusual interest in ties, socks, and handkerchiefs, hitherto items of no interest at all. He will also begin to agitate about his inadequate allowance and start wondering out loud how he can augment it by a little manual labor. He constantly asks if anyone notices how deep his voice is getting. [This does not necessarily stop after three years in college.]
It is usually Mother who sees the signs first. She knows instinctively that her son is about to take his first steps away from her apron strings. Most of what she can do for him she has already done. Soon he will probably turn more and more to his father for counsel, or to some father substitiute.
Boys usually don’t need advice on how to ask a girl for a date. [You reading this, Drewski?] They bungle through somehow in the early years of dating, eventually acquiring a certain polished technique only experience can bring. Parents can help by showing that they expect their children to date whenever they are ready. They should never force the issue or make the choices for the children.
Boys usually begin by going to games and school dances stag. They yearn from the sidelines, while pretending a vast disinterest in the equally cohesive girls. After a certain amount of this mothers often suggest, “Joe, why don’t you take Mary to the game this afternoon?” This is usually met with a derisive snort, but soon, sure enough, Mary and Joe are eating popcorn together in the bleachers. As a result of the motherly approval he needed, Joe has probably blurted, “You want to go to the game tomorrow, Mary?” And Mary has said, “Sure.” From then on making dates is easy enough.

- Amy Vanderbilt’s Complete Book of Etiquette: A Guide to Gracious Living, 1952, Doubleday