Most intelligent Modern Orthodox teenagers today, I think, have some issue that served as their first break with the "system", whether it led to their leaving Orthodoxy, re-evaluating their Orthodoxy, or just having problems with the more right-wing people who were teaching them. For some it is feminism, or mesorah issues, or Bible criticism, or Zionism. For me, this was Amalek.
It began principally in eighth grade, which I suppose is a little late for having this first disillusionment. I suppose I had problems before then, but this is the one that stands out in my mind as The Issue. Maybe it was because of the way my teacher reacted to it- an intelligent, vibrant Rebbetzein, quite right-wing, she took to having me daven at home so that she could have heart-to-hearts with me in another classroom while the rest of the class davened. I wish I could remember more about the whole thing. I don't recall any feelings of resentment; the one clear image of the whole thing is me, sitting on a desk, legs swinging, listening to her earnestly try to explain something. I think she was worried about me- I was the stereotypical "intelligent, having issues with the system" kid, questioning everything in class, making her explain. I know, because she has since told me, that she was worried about my going off the derech.
Amalek, was, of course, not the issue that I had; we also had some interesting discussions about eilu v'eilu- I remember very earnestly arguing that Rashi and Ramban could not possibly both be right about a certain subject because their opinions were mutually exclusive. I do not recall what she answered. But Amalek was the big one, the one that got me right in the gut, and one that she had no hope of answering. We must have spent several hours, over the course of weeks, sitting in the empty classroom, going over the same question, "How can it be moral to kill innocent people?" I don't remember specifically, but I'm sure she gave me all of the typical answers- if Hashem says it, it must be moral; they are inherently evil ("what about the babies?" "Even the babies." "Then what happens to bechira?" "Amalek is an exception" or something along the lines of "G-d will sort out His own"); it doesn't apply nowadays, so there's nothing to worry about. She never convinced me, and I think that I wanted to be convinced. But her answers frightened me and bothered me. A friend compared it to a Nazi "poisonous mushrooms" parable and I had no answer. (Ack! I have Godwined again. But this time it is so justified.)
I graduated, left that school, went to one that was even more right-wing. My questions did not really bother my faith. Perhaps I was too young to doubt that there were answers out there, even if my teacher didn't know them. Perhaps I am too inertial to make such a shift, perhaps I had too much faith. Whatever it was, I just thought of Amalek as being a question out there, a sort of temporary teiku (not that I had ever had a chance to learn Gemara), something that would be answered in time. I let it go.
I don't remember if it was the summer after eighth grade or the next year, but on one long family car trip to the east coast, I brought along a book by R' Aharon Soloveichik, z"tl (I'm so proud of being able to spell that. I actually have a great Soloveichik spelling story, but here is neither the time nor the place) entitled "Logic of the Heart, Logic of the Mind", which includes an essay about Amalek. I remember, very clearly, reading it on Shabbat, when there was nowhere to go and nothing to do but hang about the hotel room, since I was too lazy to go on a walk with my family. I remember also the sudden euphoria, feeling that here, finally, were answers, good answers, moral answers. I remember getting up and pacing excitedly around the room, wanting to tell somebody, and then rushing back to re-read it.
In cold blood, of course, this many years later, the argument does not seem all that radical. R' Aharon asked a series of questions on the p'shat of the Sha'ul incident, and answered them by saying that Amalekites could, in fact, escape destruction by accepting the Sheva Mitzvot, or by converting to Judaism, if they so chose. There were several proofs for this, the most convincing that I remember being the fact that there are Amaleki geirim in the gemara, and even in tanach (the man who killed Sha'ul e.g.), so obviously one doesn't have to simply kill them on sight. Again, it's a good argument and a convincing one (there being a lot more proof than I have written here), but what got me was simply the fact that here was somebody who thought my moral question was right, who was going to answer it, who had a moral answer, and, best of all, whose answer was not twisting the p'shat but also dealing with basic, logical questions. Embarrassing as it is to admit now that I have had long exposure to a more open set of beliefs, this really was an epiphany. I know that I sound sheltered, and I suppose I was, in some ways. My parents are both ba'alei teshuva, and their personal views are closer to Modern Orthodox, but my shul, school, and most of my friends were further right, and I had really not been exposed to a large degree to more critically thinking hashkafic analysis. That is to say, I was familiar with the views, but the process impressed me. And what influenced me the most was the sudden clear thought, "I was right. I didn't believe that my teacher's could be the only answer, the right answer, and I was right. I knew this had to moral somehow. I doubted and I fought, and I was right."
During my senior year of high school, I met up with my eighth grade teacher again, which is not surprising, as she lived across the street from one best friend and down the block from another. But this time, we were walking somewhere, and somehow it happened that she got to walk beside me by myself. She brought up the issues I'd had in eighth grade, and asked me if I had found answers. "You know", she said, "looking back at it, I shouldn't have tried to push answers on you. I should have acknowledged that those were good questions without trying to make you accept anything." I wonder if she is wondering whether I am still frum. She has already heard that I am planning to attend secular college, and no doubt it worries her. I tell her, that yes, I have found answers, answers that satisfy me. I don't elaborate, try to explain them to her. I say, somewhat dryly, that I am still frum, and then wonder if it sounds like "the lady doth protest too much", considering as she hasn't brought up the subject yet. I think that I thanked her for going to the effort of dealing with my questions, instead of brushing them off. Maybe that's what gave me the courage to keep looking. Who knows? She seemed satisfied, I suppose. I haven't spoken to her since, although some friends of mine still semi-idolize her and I think that they have kept her apprised of my life.
This story doesn't really have a point. Today, I'm still not sure what I believe about the Amalek issue. Although R' Aharon's answer continues to satisfy me, I am no longer uncomfortable with the idea of there being mitzvot that seem to me immoral. I can't say I'm happy with the issue today, but it no longer irks at me. Perhaps it has gone back vaguely towards a teiku. But for me, parshat Zachor is about that first thrill of having a question, a real, sticky question and slogging through it, not accepting bad answers, but not giving up on there being an answer. About the traces of that sudden euphoria in that hotel room, the sudden epiphany that neither my questions nor my beliefs are wrong, and the sudden realization that I am not alone in questioning.