Jake only cares about Kendra's money because he has a car to pay off and Anna is just an accessory to him that he really wants. Kendra has never been in a relationship with him, at most they are partners and have plans together. Yes, Jake sometimes shows chivalry towards Anna. But he also has his own conscience. He seduced the daughter of the head of the company he worked for and was fired from his job for it. When he was an intern, he was part of a secret voyeur group with old fish Marvin, where they collected photos of women at work from social media to have material to fap to. Hank has nothing to lose, not only is he retiring, but he has two years to live. So he wants to take advantage of it and not expect any consequences. Yes, I agree with you that David doesn't have many girls to fuck. Anna, maybe Kendra, I'm not sure, Alexa, maybe Mother Anna and the impossible office gossip girl Betty or something like that