The thing is that Josy had a crush with you when you were just an ordinary shy boy she worked with. And Maya starts to feel something for you after several intimate moments in which you are tender and caring. But if you keep doing dumb things and acting like a DIK, well, I can understand them having second thoughts. In fact, I'm quite comfortable with this double-check system as I feel it's quite realistic. Our MC is an immature teenager who is trying to fit in a new world so he's looking for some social acceptance from DIK's (mainly) but he also should think about how that behaviour could affect her personal relationships with the girls he's interested in. I think that realization is an important step in everyone's maturing process and I guess we'll see something similar in this game sooner or later.
Maybe you remember Megan's story from AL, when she tells you about her teenage heartbreak. The boy was nice and all but acted like an ass around his friends because their acceptance was more important for him than standing for his supposed feelings towards Megan, and finally cheated on her. I can easily picture him like your average brainless DIK. Megan decided to trust him back then, others might not want to risk it.
The issue, for me, is that you also accrue points for things that others cannot know you have done, such as checking out someone as they walk away, in an otherwise empty room. Even when, for most of the other actions directed toward the innocuous and innocent, you are a pleasant gentlemen.
Also, aside from that interpersonal issue, there is an intrapersonal one as well:
Why do you accrue points for checking women out, if they are unaware you are doing it? I mean, nearly all men I know, myself included, check attractive women out most of the time, and it isn't because I'm some chauvinistic pig, it's because I'm a heterosexual male, and that response is practically instinctual. So, why exactly would that skew our psyche, in the same way as choosing to stay and fight all of the jocks at once?