Just finished reading Stephen Dubner's Turbulent Souls: A Catholic Son's Return to His Jewish Family. Go out and read it and you won't be disappointed. Dubner's parents were born Jewish, converted to Catholicism, and raised their children as Catholics. Dubner ends up stumbling on his Jewish ancestry and being drawn to it. In the process he delves into his parent's history in an attempt to discover what motivated their conversion, but ends up (I think) discovering more about himself than his parents. Aside from the view of Judaism from an outsider's perspective which the book provides, the writing is excellent.
One point which struck me is that the Jewish personalities which Dubner makes connections to in his life are intellectual-types who come across as deep thinkers not afraid to question or to doubt. His parents were deeply committed to the Catholic faith, but that committment never led to substantive intellectual inquiry. One of the trends in Orthodoxy today that I find disappointing is the fear of intellectual inquiry that has taken root, the dumbing down of education lest students be led "off the derech" by the world of ideas. I doubt Dubner would have been as attracted to Judaism if he experienced it as a world of intellectual stagnation.