With the High Holidays quickly approaching it is time for us to take stock of our year. How should we approach teshuva, repentance, when the misdeeds are complicated and we cannot be confident we will change our future behavior? Is Teshuvah out of the question? Is there a more nuanced way for us to approach these deeds in the coming year? We discuss this subject and much more with our new moderator, Sara Rozner Lawrence. We then welcome our guest, Dr. Rivka Schwartz, Associate Principal of SAR High School, to continue the discussion and to ask – how do issues of shame and guilt around sexual practices that are not in keeping with halakha playout for teens and young adults throughout the year?