This feels like playing a mini route visual novel with every girl. Depending on values, taste, preference, you may or may not like ALL the girls. I like that its not all "perfect" with each girl, however as the audience we perceive that the first girl was optimally best (if we were playing a VN, observing 2 characters), however when he's viewing this in first person (self-insert?) he feels he might get a better deal which is comprehensible.