A person who is dear to me says he became an atheist. He still loves Jewish humor, a good Jewish joke, but refuses to come to a synagogue - even to meet his old friends there! My question is: May I pray that Hashem turn his heart to Judaism? Maybe, if he is nudged a little, he will make the rest of the road on his own feet. But isn't Hashem expecting that a person turn to Him of his own volition? He gave us freedom of will so that we could discern good from evil and make the right choice, and my concern is that I may be asking for something self-contradictory. Is it ethical to pray that another person become more Torah observant?
I'm touched by your question. From a logical point of view, your question is very sound. Doesn't G-d want us to observe the Torah through our own free choice?
Clearly, it is a mitzvah to pray that our fellow Jews should return to the Torah path, just as we pray for ourselves in the daily prayers, "Return us, our Father, to your Torah."
But does it make sense to pray for someone to become Torah observant? Doesn't this contradict free will? Not really. You see, every person, Torah observant or not, has free choice. So, when you pray for someone to become Torah observant, you are praying that his free choice be changed from one level to another.
For example, right now let's say that his free choice level is "Should I eat one ham sandwich today or two?" We pray that he become a Torah observant Jew, and then his choices will be on a higher level: "Should I study Talmud for one hour today or two?" We pray that his free choice level be elevated to that of a Torah Jew.
Another answer to this question is that we pray that G-d put the person in a situation where it will be easier for him to choose to keep the Torah. For example, let's say a person doesn't keep the Torah because he never had a good Torah education. Through your prayers, G-d can open an opportunity for him to learn about Judaism; for example, he "bumps into" an observant Jew who invites him for Shabbat.
- Responsa Iggrot Moshe, Orach Chaim 4:40:13
- Avotot Ahavah, by Rabbi Mordechai Becher and Rabbi Moshe Newman