Rav Yosef Dovid Josilowsky
Answer: One might assume that this is not Lo Sachmod because he is asking to be given a gift of more support, not trying to buy a specific item. However, Rabenu Yona says that compelling someone to grant you a gift is also a violation of Lo Sachmod. The Chofetz Chaim writes that it is quite common for chassanim to badger their fathers-in-law for more than the agreed-upon dowry. He warns against doing this because, according to Rabenu Yona, it would be a problem of Lo Sachmod.
Rav Moshe Sternbuch (Teshuvos V'Hanhagos) suggests that this may not be a problem if the reason the groom is asking for the additional items is in order to provide for his wife and children. Perhaps this can be framed as a benefit to the Father-in-law as well, which may mitigate the transgression.
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