By Horav Yosef Yeshaya Braun, member of the Badatz of Crown Heights
My friend is thinking of giving a ring and saying the words “will you marry me” to a girl he is dating. Is this a Halachic issue?
The problem with a Chasan giving the Kalah a ring before the Marriage under the Chupah, particularly in the context of an engagement proposal and using words associated with marriage, is very serious. Using a different piece of jewelry or any other gift in the context of an engagement proposal is also problematic.
It is not only an issue of Chabad custom, but a Halachic problem involving a question of potential Kiddushin prior to marriage — and quite serious consequences if they separate C”V. It also puts the Beracha of Kidushin under the Chupa into question.
This idea should be strongly discouraged.
Is it better if I push him to give the ring at a different time after he proposes?
It is best to give other jewelry in general (except at the engagement proposal where no jewelry or gifts should be given other than food). If you can’t convince him out of the idea of giving a ring, it shouldn’t be accompanied by any talk about marriage and should be given preferably through another woman.
Can I send my future bride, via her sister, a letter that she will read on our wedding day?
It is permitted. Of course, one must be certain that the letter is indeed suitable to be read on such a holy day, which is like Yom Kippur.