Thanks for taking the time to elaborate; perhaps I didn't convey what I meant well, so I'll try to elaborate a bit more on my end, too.
When I said 'assertive and confident', I didn't mean in relation to his position in 'La Famiglia' - acting like an idiot in a situation where being assertive would be suicide; of course I understand if he's entry level mafioso he's gonna follow orders without question if he wants to survive. I meant assertive and confident in his personality in general. So like, comfortable with who he was, confident with the women, etc, and not a pushover who doesn't know how to handle women. Think Ian from Our Red String, for example (if you know the game).
I've just come across way too many games where the guy is meant to be 'relatable' by the player, but 'relatable' really just ends up equating to 'pathetic'. So they either have no real confidence nor experience with women, or they act in a way that makes it clear the dev doesn't know much about how a naturally confident guy acts around women... yet somehow the guy manages to get all the women regardless. I don't enjoy those sorts of games at all, and that's the main reason why I asked this question in the first place.
In short, I prefer the games that feel a bit more realistic in character behavior/portrayal all around.