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There were always affairs between those who were not afraid of retribution and women under the protection of weaker men. The point is that approaching a stranger, a woman whose protector wasn’t known to the approacher was very, very dangerous.

For most of history, killing a man for sleeping with a daughter or wife was written into law.

Women were locked in their homes when night fell. Women who were seen at night alone in public were immediately assumed to be prostitutes.

According to the Wikipedia entry on marriage, all marriage prior to the 17th century was arranged.

The idea of a public square where single women could talk to strangers is a fantasy. Even courtly love was more the equivalent of modern online dating – initiated by communication in writing – than modern pickup.

It is no coincidence that public speaking is almost as stressful to us as approaching women. It is a form of asserting power, an act that, for most of human history, was considered very dangerous. This has nothing to do with social conditioning. We are not told that we should fear speaking in public because the Church thinks it’s bad. And yet our reaction is nearly identical to the other form of asserting power, approaching a random stranger of the opposite sex.

The average single man in the United States today approaches several women per year. This is in a fairly open minded, egalitarian society. Under the conditions that I just described – fewer single women in public, danger, arranged marriages, etc. – it must have been harder still in our past. Given how little practice most of us have doing this thing, by what logic can you possibly assume that it is natural for us? What other activity – one that is not related to mating – that we engage in so infrequently and has such consequences for our lives do you also consider natural?

Here is what I think. Men who trivialize this fear are prolonging it. To say that approaching is natural and easy is to say that you have a problem that other people do not have. In fact, most men share this problem. Offering a specific explanation for it – one that is related to your childhood and past – is a form of exceptionalism that prevents you from moving forward. Accept that this is tough. Accept that this is unusual. Accept that you need to work on it a lot to overcome your NATURAL fear. It’ll make things a lot easier.