In "The Magic Barrel," why is Leo disappointed in his date with Lily?
Leo is disappointed and a little angry after his date with Lily because he feels that the matchmaker, Salzman, has misrepresented him to her. Lily is very interested in "how it was that (he) came to (his) calling" as a rabbi, and evidently has been led to believe that he is a man who is very close to God. In reality, Leo is uncertain about his faith, and is forced to admit that he is "not...a talented religious person." In a moment of forced self-reflection, Leo realizes that he "came to God not because (he) loved him, but because (he) did not."
Because of the questions Lily keeps asking him about his spirituality, Leo is convinced that Salzman has presented him as a pious man, which is not what he is at all, despite his chosen course of study as a rabbi. Leo feels that Salzman misrepresented Lily to him as well, because she is clearly much older than the twenty-nine years the matchmaker has declared her to be.
Leo is not sure what he is looking for in a woman, and comes to understand that he is sadly incapable of love. His requirements in a mate tend to be artificial; Lily, though she is "surprisingly sound" in his estimation, is not a beauty, nor is she young. Somewhere in the back of his mind, Leo is looking for excitement and sexual attraction first and foremost in a relationship, and Lily's probing questions about the nature of his spiritual life are disturbing to him, to say the least.