As a reform Jewish high schooler in a medium sized Jewish community in the South, I was not particularly seeking any new form of spirituality. I was moderately involved Jewishly and was even on the local chapter board of
NFTY (the National Federation of Temple Youth). Based on my exposure at that point (aside from some semi-Jewish poetry in the back of our "
Gates of Prayer" prayerbook), I took it for granted that Judaism is a fairly shallow enterprise.
For example, in
sunday school growing up, every Sukkos we went out to the Temple's Sukkah and the rabbi explained the significance of waving the four species. He always said that "We wave them in all six directions to remind us that G-d is everywhere." It was the same explanation year after year, from the early grades through early high school. It was mostly the same with respect to the other aspects of Jewish practice they taught us about. But aside from the fact that I found these teachings boring, the superficiality did not really bother me very much. I just assumed that one-line pat explanations like this were what Judaism consisted of. And that was that.
Over Channukah my sophomore year in high school, however, I met a couple of orthodox kids at an inter-youth group event at the JCC. Because I fancied myself an open-minded person with respect to people of "other faiths," I interestedly asked them about orthodoxy. To my surprise, their answers to why they did this or that thing were not the kind of pat one-line answers I expected based on my own Jewish experience. There was depth, common sense, and thought-out explanations for each detail of what they did. This depth fascinated and attracted me and was the impetus for me to continue my friendship with them. This process led me to begin attending a Torah class for teenagers and eventually become observant myself.
Fast forward several years later, through post-high school yeshiva and eventually kollel: Over time, I learned how to learn Torah from the original sources, but there was something about the Gemara and Chumash that did not completely satisfy me. I often found Gemaras (sometimes Agadata and sometimes not) which screamed out to me that there was a deeper meaning to the text. As Rashi always says, "אין המקרא הזה אומר אלא דרשני."
See, e.g. Rashi on Bereishis 1:1.
I searched through the perushim in the Gemara, the Ain Yaakov, and the seforim commenting on the Gemara found in most batei medrash. Maharal in Chiddushei Agados sometimes "hit the spot," but it was slim pickins'. It seemed that almost nothing went down beneath the surface of the Gemara's simple meaning. As for Chumash, when I had that feeling, I looked through all of the meforshim in the Mikra'os Gedolos and other seforim on the Chumash with similar results (although Kli Yakar and Ohr Hachaim were often very helpful). I eventually came to expect that maybe that deeper meaning and current relevance of the text either did not exist or was simply not accessable to regular people.
This perception began to change when I discovered a sefer that is sometimes found in more Litvish circles:
Ohr Gedaliyahu, by Rav Gedalia Schorr, a Rosh Yeshiva of Torah Vo'Daath. He was very connected to Gerer chassidus and I began to learn certain basic concepts of Chassidus from these seforim. I felt like I was finally starting to go
down the rabbit hole just a little bit.
Part of the time I was learning in kollel, I worked in the evenings for a "kiruv follow-up" organization called
Hashevaynu. Rabbi Zakutinsky, the founder and head of the organization, is close with
Rav Moshe Weinberger, so he persuaded Rav Weinberger to come to their first few retreats, which I attended as part of the organization. Rav Weinberger is a Chassidish Rav who lives and teaches Torah in the modern orthodox community of Woodmere, in Long Island, New York.
Although I had heard Rav Weinberger speak at my then-fiancé's (now-wife's) suggestion, the Torah and Chassidus he taught at those retreats were so deep, so real, and so true, that it made me feel like I was discovering an aspect of Yiddishkeit that I had always felt
must be there, but never experienced.
I subsequently got a job as part of a community kollel in the Midwest. When I got there, I quickly ordered over 100 of Rav Weinberger's
tapes (that dates me, I know). I listened to these tapes as I traveled to various college campuses giving shiurim and they had a deep effect on me. When it was time for my family to move to a larger community for chinuch purposes, we moved to Woodmere in order to be closer to Rav Weinberger.
Over time I attended many of Rav Weinberger's shiurim and began learning more sifrei Chassidus like the
Me'or Einayim,
Toldos Yaakov Yosef,
Tzidkas Hatzadik, and the
Tanya. The clarity of the
Bilvavi Mishkan Evneh seforim also allowed me to go even deeper down the rabbit hole to gain a greater perspective on Judaism, a practical road to achieving my purpose in life, and a deeper understanding of all reality. In this respect, Volume 5 of the Bilvavi series and his seforim on Chumash are especially powerful and perspective-changing.
The common denominator between my discovery of Yiddishkeit in general and my discovery of chassidus in particular, is that I found a deeper life path in both of them, compared to what I was exposed to before. I feel that it is the pure chessed of Hashem that he revealed the Torah to the world through Moshe Rebbeinu and chassidus to the world through the Baal Shem Tov. It seems like the majority of people, both in the outside world and within the frum community, are satisfied with a life of superficiality. So I am thankful for Yiddishkeit generally, and chassidus in particular. B'chasdei Hashem, they are there to offer a deeper path to those who seek it out.
I saw the most amazing drush by the Rambam quoted by Devorah in her Voice After the Fire blog. 
