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 class pres in part because he called her 'perfect', something she has a bit of a complex about. He failed with the gyaru because the gyaru has stated the world is cute, but only the mc is 'cool'. Even if she likes cute things she doesn't like them romantically.