Not wishing to speak for Silas, but it looks to me like this. You believe that:

I have the firm belief that no one becomes good at conversation, dating, or any social skill without the equivalent of "creeping out 20[0] people in a row"

If you believe that you are not good at conversation, then you are speculating without practical experience. If you believe you are good at conversation, then by your account you must have gone through your 200 people. Silas is challenging you to share your experience of doing so -- I presume as a check on whether you really believe it, or merely believe that you believe it.

Creeping out 200 people in a row is like suggesting you can't learn to ride a bicycle without breaking a few bones. It's way excessive. Even creeping out 20 people in a row (Silas' figure, which you chose to amend upwards, which argues against this being idle hyperbole) is an absurdity. By the time you're creeping someone out, you're already way off course.