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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?

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    男の modifies A. A who is male, and secretly popular among girls... – marasai Oct 30 '18 at 9:08
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うまく行く here just means "(things) go well", "do the job", etc. が is a subject marker, and A言う clearly means "A says (something)", not "speaking of A". There are both 方が and より, so what's compared is very explicit; "A says" versus "B (says)". If you don't know how to compare two verbs using 方, see this.

Aが言う方がうまく行く。
Things go better if A says it.

Aが言う方が、B(が言う)よりうまく行くだろう。
(I suppose) things will go better if A will say it than B (will say it).
A should be the better person to say it than B.

This 踏む is "to guess", "to figure", "to estimate", etc. You can tell it because it's used with a quotative-と.

「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。
(It is that) I figured that A would be the better person to say it than B.

"男の" and "女子の間でひそかに人気のある" independently modify "A". You can tell this because there is a comma and しかも. 密かに here means the fact that A is popular is not openly known, so I'll translate it as "actually".

「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。
I figured that A, who is male and actually popular among girls as being a little cute, would be the better person to say it than B.

So A is the person who is trying to make a suggestion. Are you sure you have read the previous context correctly?

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