How to Chat with a Woman

c. 1180s

“After greeting the lady, the man should allow a moment or two to elapse to permit the woman to speak first, should she so desire. If the woman herself starts the conversation, you will have good cause for satisfaction, assuming that you are not a fluent conversationalist, because her comment will give you plenty of topics for discussion… But if the woman delays too long before beginning to speak, you must after a short pause cleverly break into conversation. First make some casual observation with an amusing point, or praise her native region or her family or her person.”

Andreas Capellanus, De amore

Man: Hello.

Woman: Hi.

Man: …

Woman: …

Man: You’re from Aquitaine, right? Aquitaine is so great.

Woman: …

Man: I like your tunic.

Woman: …

How to Sweet-Talk Your Lady, 1656, here.