The following is a brief summary of some of the 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.
When Yosef accuses the brothers of stealing his cup at the end of Parshas Mikeitz, Yehuda responds in Bereishis 44:16 with a statement of contrition. However, when the story continues at the beginning of Parshas Vayigash, Yehuda is less apologetic. In fact, Yehuda cautions Yosef in Bereishis 44:18 that Yosef should not get angry at him. Rashi explains that the reason that Yehuda says this to Yosef is because Yehuda spoke harshly to Yosef at this time.
R' Frand then asked the obvious question - what changed from Mikeitz to Vayigash which could explain why Yehuda was now speaking more harshly to Yosef?
R' Frand answered by quoting the Or Hachayim HaKadosh, who explains that until now, the brothers felt that their ordeal was a punishment for how they treated Yosef. As such, they accepted that this was their penance and they did not push back. But after Yosef told them that they can all go and only Binyamin should stay, they realized that this was not from Hashem. They perceived that Yosef was being an achzar and they changed their tune to be more confrontational.
R' Frand next quoted the Vilna Gaon who observed that the trop (the cantellation marks) on the first pasuk of Vayigash is Kadma V'azla Revi'e Zarka Munach Segol. These notes tell the story that Yehuda, who was the fourth son (revi'e) got up and went (kadma v'azla) to Yosef. Why did Yehuda do this? Because he had previously promised Yaakov that if he did not bring back Binyamin, he would forfeit his place in the world to come. This can be translated as zorek (thrown out) from munach (resting with) segol (the Jewish nation).
R' Frand's final vort discussed the story of how Serach, the daughter of Asher, hinted to Yaakov that Yosef was still alive. The Medrash explains that Serach played a musical instrument and sang a melody to Yaakov of "Od Yosef Chai." The Sefer HaYashar explains that the brothers were afraid that if they told Yaakov outright that Yosef was alive, the shock could have killed Yaakov. By having Serach sing this song to Yaakov, when the brothers showed up later to tell him that Yosef was still alive, Yaakov was not as shocked.
R' Frand quoted R' Pa'am who said that we learn from this that a person needs to be careful about how to discuss things with others. He quoted a R' Yaakov Bender, a principal in a local yeshiva, who had a rule for contacting parents. When he called a parent, he always began the conversation, I am Yaakov Bender and your son is fine. This immediately put the parent at ease as a call from a principal can be stressful enough.
I personally had a moment like this about eight years ago, when I was informed by my secretary that the principal of Penina's school was on the phone and "she had to talk to me." When I picked up the phone, the principal began the conversation by saying, "I had to call you to tell you something very important." My heart began racing and I had all sorts of thoughts. The principal continued, "your second grade daughter just told the most incredible dvar Torah." My heart calmed down and I was struck by a sense of relief and pride in my daughter and ... a feeling that I wanted to kill the principal.
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