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polymathwannabe comments on Open thread, Sep. 14 - Sep. 20, 2015 - Less Wrong Discussion
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So how does getting sexual experience with prostitutes translate over to getting into sexual relationships with regular women through dating, any way?
I met a 20-something woman at the Venturist cryonics convention in Laughlin, Nevada, last year who talked to me more than she needed to as a social acknowledgment, which made me wonder if she felt attracted to me. I don't know how to interpret these situations in the handful of times they have happened in my life, so I don't know what to do, and they make me anxious.
If I had sexual learning experiences only from prostitutes, and I had nothing else to go on, should I have asked this woman how much money she wanted to come with me to my room in Laughlin's hotel for sex?
That generally doesn't work on women who don't already sell sex for a living.
Maybe a sex surrogate could be useful for you. She would provide you with more emotional and social guidance than a regular hooker, and the learning process would advance at your own pace and on your own terms.