Contemplations of a Closet Curmudgeon

I dunno, I love Gene Kelly and the music and dancing are sublime but the plot always gets to me. He can't possibly be interested in a relationship with a woman who's more powerful and rich than he is (because The Man Must Wear The Pants), so as a penniless artist he goes after the only person more pathetic than him - an orphan. Even though she has zero interest in him, furthering the male delusion that if you just stalk and harass a girl enough she'll suddenly fall in love with you. Ugh.