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Here is the thing.... Darth Hank
Anna finds Hank disgusting so he isn't going to win any points as a breeding bull for her, if its seriously Anna's desire to have another child. All Hank has is information, influence and a position of power. Yet his window of opportunity (with plausibility) is he has to either win Anna over or break her.
Winning her, sure he could leverage his influence to help save David's business and thus she might give in. Problem, is Anna is even more upset with David after her phone call with Marcel. So her motivations are not what they should be... she still loves David but is deeply hurt. But Anna also is a calculator and not stupid. She calculated to keep Chris on her side and it's just as likely that if David's company goes to hell, David wouldn't have the resources to afford a protracted divorce/custody case. All that means is Hank hasn't much of a position against Anna with influence. Worst still Anna is in the world of lawyers and the law. Even if she isn't school well in family law, it's safe to assume she knows who is and has access to the best... and one more possible long shot is the dinner date with Grant, another attorney. Now this goes to me thinking not of the character's plots and motivation but the game developers. Something has to happen during the Anna/Grant dinner date. Assume a player picks the path to reunite Anna and Grant, Anna has one more ace. And since Anna is hoping for the best but keeping the worst in mind and it's a plausible plot point...well maybe.
Going back to power and influence, sure Hank could offer to help Anna and David, but does Hank want David in the picture at all? If David gets destroyed, then Anna who has a job is just that much more vulnerable in having to keep it. So what is Hank's long game? Sure, he wants his thrill with Anna, but that is the short game. So winning Anna comes down to power.
Breaking Anna relies on any lingering daddy issues Anna may have. In Chapters 1 and 2 had the developer didn't work with Anna's desire for male attention much, Anna could be thrilled with his attention but still be disgusted with him. In a way it could have been her own private game of "oh yah, look all you want, but you're not going to get any." But that trope wasn't hit hard upon but submissive was... it's a path route to Anna. And having been dominated all her life, Hank domination could be another forum of it that is controlling like her father, but with an added dimension of having to yield to a powerful figure like Hank.