Stars, I think the amount of thought and emotional energy you put into this proves you're not a bad person at all.

There are multiple sides to this. What he did is a shocking upheaval of the existing relationship dynamic. This has to be an accepted risk for anyone when trying to change from a friendship to a romantic. You often can't go back and it really changes everything. His expectation that he can have his cake and eat it too is just immaturity. You can't just spring that on someone and then if they're not interested hit the rewind button to go right back to the same friendship dynamic.

I think what you describe is a reasonably common occurrence and it does sometimes break the friendship due to awkwardness. I think that may just be human nature in some ways. Don't give up on having male friends tho!