Why the need to say בו in the Mishna when the permissibility of Kiddushin with a messenger is already enumerated? The Gemara's second answer, that of Rav Yehuda in the name of Rav, is fascinating. Rav Yehuda says that we learn from בו that there is an איסור for a man to be מקדש a woman without seeing her. Proof: ואהבת לרעך כמוך. The man may be disgusted by her appearance, and he is thus violating this Pasuk, for he will not love his wife. Or that is what the Gemara seems to say on the surface.
However, when looking deeper, Akiva Somer (with Rav Feigenbaum's עזרה) offered a modification to the above reasoning. The איסור is not an איסור. Say what?? Rav Yehuda is truly coming to offer a recommendation to not storm into a marriage with a girl you've never seen. This may (and according to Sir Isaac Graber, almost always) lead to tension between bride and groom, negativity between the in-laws and a divorce. Yes, not the best ואהבת לרעך כמוך scenario. Therefore, in order to prevent such repercussions, Rav Yehuda adds a recommendation for the man to not jump into a haphazard marriage.
But what should the man do? Rav Yehuda's answer: See her.
Without careful analysis, this answer seems superficial. Unless a person has a super power to look at a woman and immediately recognize all her characteristics, strengths and faults, it seems that Rav Yehuda can do better. Nevertheless, we should view his answer again not as the ultimate solution, but rather as a minimal recommendation. A man should at the very least look at her external appearance, and by doing so, he will have eliminated the massive barrier between he and herself. Of course Rav Yehuda would say the man should spend time with the woman to ascertain whether she is the one. Looking at her appearance at the very least will trigger a connection of some sort beyond random marriage, which as mentioned before, may have triggered animosity and sin.
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