Jeph may not intend for it to be harassment, but that doesn't mean that it isn't. Intent matters, but it is not everything.
You shouldn't be ashamed of being a virgin. I never was. The only reason I would get annoyed if someone assumed (correctly at the time) that I was is because of the assumptions that usually go along with that. The assumptions about me as a person. So if someone I don't know well makes the assumption that I am out of nowhere, that's probably not all they've assumed.
If you said "Faye and Dora" in place of "Jeph", that would be applicable. I don't think anyone is saying Jeph is harassing, and he has written characters that do not think they are being harassed.
In general, shame isn't involved, it's just a status (unless the individual is immature and in a teen comedy). The reasons for that status, however, may sting a bit.
Anyone who wants to do the WCDT this week, go for it.
I had my fun. And ran out of poll ideas.