There were examples of being mean to men given - insulting their manhood, or other attempts to cut them down. I suppose if it's belittling which attempts to make a man seem less masculine that's when emasculating fits. However, being myself instead of some image a dude has of what he wants women to be is in no way emasculating.
I've had men I've met who were rude jerks, but not who said the things above. I just didn't bother with them, because it's not worth the energy.
As far as intimidating? Oh, I get that plenty. I also have had men tell me that they never hit on me because they knew as soon as they met me I wasn't the type of woman with whom to have a fling. All are fine with me - usually when men tell me I'm intimidating it's in a nice way, and tied to the second statement.
I don't have much need for people of either gender who only have interest in those who throw themselves at others, either in friendship or romantic interest. This guy sounds like his "language of love" is in doing things for others, so he wants others to do for him. That's ok, but it sounds like he's being whiny in what he's asking of you. If anything, dude's making himself seem less masculine! I think he's probably interested in you and hoping you'll do something so he can convince himself the interest is mutual based on your description of his behavior. But then again, it kind of sounds to me from your description like he's the type who would string along multiple women at once, and wants you to be one of those women.