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Stuff she did you would not do even for a lover.
Boss is younger than Date, I believe. But then again, so is Hitomi! I guess it depends on whether you want your protagonist to be a creepy mouth-breather or a borderline paedophile.
I'm writing this under the impression you've finished the game, so spoilers if you haven't.
Except Pewter setting her personality (which is never stated to be to his preferences, just that he set them, since if it were to his preferences Aiba would probably be male) could have been done to resemble the Boss since he was the only one besides the two of them who knew their history and what any previous relationship may have been, or at least has some idea of Boss' feelings on the matter due to one of his final statements to Date (to paraphrase) "everything the Boss did she did for you" and "so what is she to you?", and Aiba's comment about physically being set to Date's preference may be more about her appearance and facial/hair details than her figure. Also the Boss can't be that much younger than Date, or at least not enough to affect their relationship, considering that they were in the same class of police recruits and had been friends for years.
Also Date is an equal opportunities pervert since for all his talk about only liking large breasted older women (which I personally think is him posturing/compensating for his actual tastes with how much he mentions it) he still shows an attraction to/makes pervy comments towards (at least in his mind) the receptionist, the mermaid waitress, and even Iris. Hell, even Aiba once or twice.