I've never dated or slept with a woman...

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splodeymissile posted...

Naturally having a relatively low desire for intimacy is quite a bit different from actively wanting sex and relationships, but failing to get it.

And knowing how and when to be assertive when appropriate is a skill that people should and most do develop. Passive people might not get it as often, but they still usually manage something of a healthy sex life precisely because they can adapt to a given social situation when needed without feeling like they're compromising their core personality.

I'm unsure about that. While only some men I know aren't intimately assertive, almost no women I know are. Or at least, they aren't in the initial stages of dating. Expectations for mastery of this skill seem to differ.
Stop it. Get some help.