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I have often witnessed that poking/testing/challenging that you describe between you and your brother. It always struck me as stupid and sad, and telling more about the questioner than the questionee. Women might be slightly less prone to it but they're as quick to judge: this girl doesn't date, she must be gay. That need to put people in boxes and sticking a label on them probably goes back to living in caves ad finding security in close-knit clans.

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