A is a guy and B is a girl. b is trying to set up A with another girl. Neither A or B's social life is that clear yet but A is somewhat of a mood maker.
男の、しかも女子の間でちょっと可愛いと密かに人気のあるAが言う方が、Bよりうまく行くだろうと踏んだのだった。
among the guys or girls, more so the girls, A was secretly popular because of his cute features, speaking of A (as oppose to not A), was deemed to have had(experienced?) more peaceful relations that B (with everyone?).
there definitely no homosexual vibes in this content, is 男の not related to 間?
is there any difference between Aが言う方が and Aの方が?
What's the best way to read 踏む in this sentence?