I like how the three girls all reject him for reasons completely in line for their previous personalities rather than just an inherent dislike. He failed with the tsundere because he never had a pre-existing relationship with her so flirting just comes as odd and uncomfortable. He failed with...
Extremely late, but Silence of the Lambs has one over the mouth. It might be referencing another piece of media, but this is the one that pops into my head.