The following is a brief summary of some of thoughts said over by R' Frand on the parsha this evening. I have attempted to reproduce these vorts to the best of my ability. Any perceived inconsistency is the result of my efforts to transcribe the shiur and should not be attributed to R' Frand.
R' Frand began the parsha vort by making reference to the Aishes Yifas Toar ("AFT"). He noted that its hard to comprehend how this was permitted, but noted that Rashi explains that the Torah addressed a person's Yetzer Harah in permitting this.
R' Frand quoted R' Eliyahu Schlesinger in the Sefer Aleh HaDevarim who adds another level of complexity to the question. He notes that the people who went to war were those without sin as we saw in Parshas Shoftim that people who were afraid due to their sins - even if the sin was just speaking between putting on the Tefillin Shel Yad and Tefillin Shel Rosh was enough a reason for a person to be kept back from war.
R' Frand digressed to mention that the Maskilim in Europe had put on a play about those who qualified to go to war and as a parody suggested that only the Chofetz Chaim and R' Boruch Ber would have been able to go.
But with all this, how does this soldier wind up wanting an AFT?
R' Frand explained that it was due to the environment as war is unlike any other environment. The soldier is a Tzaddik because he grew up in a sheltered environment where everything was holy. He is thrust into war and he cannot cope with what he is exposed to. The Torah recognizes that he may not be prepared for this and takes it into account.
R' Frand said that this can be viewed in today's world as well. A boy begins by going to elementary school and then high school and Yeshiva and he is in an environment that is entirely Torah. But when he goes to war he can wind up in "Corporate America" and an environment which is antithetical to Torah. R' Frand said that when he was growing up people needed to go to college and then to the Olam Shel Sheker and people could not cope with it. But now there are frum businesses and ways to make a Parnassah without being in that environment. Because we see every week that in Corporate America, every week there is a CEO who loses his job because of an improper relationship.
Of course this is not always feasible as becoming a lawyer or a doctor requires schooling and beyond. But R' Frand advises that a person should work in a place with others like him so that they can remind him when he is doing something wrong.
R' Frand also referenced to the Mitzvos in Devarim 23:19 of "לֹֽא־תָבִיא֩ אֶתְנַ֨ן זוֹנָ֜ה וּמְחִ֣יר כֶּ֗לֶב בֵּ֛ית יְהֹוָ֥ה אֱלֹהֶ֖יךָ." He quoted the Ramban who explains that it was not uncommon that a זוֹנָ֜ה would want to bring a sacrifice from the ill gotten gains and say - I am bringing this even though I did something wrong. The Ramban says that accepting this sacrifice would encourage her to continue to act this way and relieve her guilt.
R' Frand observed that the worst thing a person can have today is guilt, but guilt is a wonderful emotion. We don't eat until we burst, because Hashem wired us to feel full and stop eating. Hashem also created guilt so that a person feels bad about what was done wrong, as the guilt allows for Charata which is the first step of Teshuva. Meanwhile the זוֹנָ֜ה is trying to avoid feeling guilty and to continue her actions. R' Frand closed the vort by comparing this to people who make a lot of money in illegal ways and they feel bad about it and want to donate to charity. Its wonderful to donate, but if its done to alleviate the guilt and encourage more bad practices, it does not make Hashem happy. This is the lesson to us from a Mitzva which would seem to be applicable in our generation.
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