Some women are quite understandably
very hinky about one on one encounters with men in any situation. I owned a business where I would do in house sales calls to sell remodeling services. Most of my customers were women and I would go out of my way to make sure they were comfortable. Still I recall one woman who would come outside in the garage to talk to me but when she went back inside the deadbolt would clunk very audibly. I thought it was weird but I wasn't offended, I just finished up my quote in the garage.
But you would think that most folks out for a ride would at least be polite to other riders in the absence of any reason to be otherwise.
Plus: kudos for not getting offended by that customer. Many dudes would've taken it personally, even though it has nothing to do with them as an individual.
Regarding 40-tude and the woman who asked him not to draft: it could be because she is female, it could also be because you were in her personal space , that you were uninvited, that you were a stranger, or that she prefers to ride alone.
Regardless, if you try to force your presence on someone who doesn't want you there, for whatever reason, you shouldn't be offended if they ask you to not be there.
I'm not saying you can't share the bike path, just don't sit inches away from someone who doesn't want you there.
Strangers who jump on my wheel get politely asked to not do that as well. If I don't know you, I don't want you anywhere near enough to cause me to crash.
Nice bikes and fancy kit only means someone can afford those things, not that someone has good handling skills. People crash expensive sports cars all the time because they don't know how to drive. Nice bikes are no different.