Dear Jew in the City, Why is it a mitzvah not to free a slave? That seems pretty messed up. – Moshe Dear Moshe, Thanks for your question. Before I answer, let me contextualize things for readers.  We previously discussed a question about slavery, specifically how American Jews might or might not have participated in […]

Dear Jew in the City, Why didn’t King David deal more harshly with his son who raped his daughter? Why didn’t Yaakov react more strongly to Dinah being raped? – Jason Dear Jason- Thanks for your question, Jason. I understand where you’re coming from, but I think you’re making a lot of assumptions about what […]

Dear Jew in the City, What are tzitzit and why do Jewish men wear them? Sincerely, Jack Dear Jack, Thanks for your question. Just a heads-up, you said tzitzit, reflecting the Sephardic pronunciation, but I’m going to use tzitzis, à la the Ashkenazic. The answer to your question is fairly straightforward: we wear tzitzis because […]

Dear Jew in the City, What is the difference between guilt, regret, and feeling like a bad Jew? For example, I didn’t fast on the 10th of Tevet when I didn’t feel well, so I feel like a bad Jew. Sincerely, Shaindy Dear Shaindy, Thanks for your question. It’s one I’ve had a lot of […]

Dear Jew in the City, Let’s say a teenager wasn’t able to express his real thoughts growing up, because his parents actively silenced him, gave him the message his opinion wasn’t wanted or didn’t meet his emotional needs in a significant way? In order to heal, he’s supposed to go through different stages of emotions. One […]

Dear Jew in the City, I was told you can only seek medical help on Shabbos if you’re certain it’s life or death. Is there more leniency you can rely on? Sincerely, Chani Dear Chani, Thanks for your question. Before I address it, I want to make two things clear: (1) here, we answer questions […]