When one grows up in a very regimented society, it's not unexpected to have very clear examples of the right way to live one's life constantly pointed out. Conversely, it's also not uncommon to have many examples of the absolute wrong way to conduct oneself also highlighted. In both subtle and straightforward ways, one can often hear the messages conveyed of "how a ben-torah is supposed to behave", or how one shouldn't do X because "that's how shkotzim act", etc. Most of the time I'm sure these messages have their intended effect of influencing individuals to conform to the prescribed image. Yet there are also times when, even as one professes loyalty to the stated dogma, one can't help sense a flicker of uncertainty regarding these portrayals, because deep down, one feels some sort of connection to the questionable activity. And not just in the sense of a weakness or base attraction, but an authentic and genuinely sincere affinity.
For me, one of the most acute examples of this experience has got to be the point in the pesach seder when we read about "The Wicked Son." The haggada describes one of the four sons as not being very interested in all the rituals, and openly questioning why he must be involved in them. For this appalling crime he is branded wicked. Growing up, what was I supposed to tell myself as I read this section? While I might not have consciously admitted it to myself, I knew very well that I totally identified with this characteristic of the wicked son. Despite my being a dedicated and properly behaved frum kid who for the most part took all of his religious duties quite seriously, in some deeply hidden part of my heart that I dared not explore, I knew that I would much rather be without all these burdensome practices. Of course I wouldn't have ever contemplated doing so, but if I had ever allowed myself to express myself as this son did, I'm sure it would have been a highly cathartic experience for me.
But this kind of behavior is wicked! It's wrong! It's bad! And how do we deal with such defiance? We knock his teeth out. True, it might seem excessive, but this is the Torah way of dealing with such people. And in case he doesn't get the message from his divinely ordained thrashing, afterwards we unambiguously let him know how we feel about his kind: "If you had been at Egypt you woudn't have merited being redeemed." i.e. "We don't even want you."
With traditions like these ingrained into our religious experiences, how can people wonder what makes some of us feel less than positive towards religious Judaism?
(PS - Another example of an "official" portrayal that always made me uncomfortable was the text in the Hadran: "We work, and they work... We run and they run...".)