Teshuva as a Guide to Repairing our Intimate Relationships -Episode 15 (BONUS EPISODE)

During the month of Tishri, we engage in a process of Tshuva; self-reflection and repentance. Through prayer, we repair our relationships and connect with God, with ourselves, and with those we may have hurt. In this mini episode, join Rabbi Scott Kahn and Talli Rosenbaum as they discuss how the basic elements of the tshuva process can serve as a model for healing and repairing our relationships with ourselves and the significant others in our lives.

Rambam Mishneh Torah, Hilchot Teshuva 2:2:

ומה היא התשובה? הוא שיעזוב החוטא חטאו ויסירנו ממחשבתו ויגמור בלבו שלא יעשהו עוד שנאמר יעזוב רשע דרכו ואיש און מחשבותיו. וכן יתנחם על שעבר שנאמר כי אחרי שובי נחמתי… ויעיד עליו יודע תעלומות שלא ישוב לזה החטא לעולם… וצריך להתודות בשפתיו ולומר עניינות אלו שגמר בלבו.

What is repentance? It is when the sinner abandons his sin, removes it from his thoughts, and determines in his heart that he will not do it again, as the verse states, “Let the wicked abandon his way and the wrongdoer his thoughts.” And similarly, he must regret the fact that he transgressed, as the verse states, “For after I returned, I regretted…” And the Knower of Secrets will testify about him that he will never return to this sin ever again… Additionally, he must verbally confess and speak aloud these ideas that he resolved in his heart.


Masechet Yoma 86b:

 אמר ריש לקיש: גדולה תשובה שזדונות נעשות לו כשגגות שנאמר שובה ישראל עד ה’ אלהיך כי כשלת בעונך – הא עון מזיד הוא וקא קרי ליה מכשול. איני? והאמר ריש לקיש: גדולה תשובה שזדונות נעשות לו כזכיות שנאמר ובשוב רשע מרשעתו ועשה משפט וצדקה עליהם יחיה! לא קשיא; כאן מאהבה כאן מיראה.

Reish Lakish said: Great is repentance, for [through it] intentional sins are treated like unintentional sins; as the verse states, “Return O Israel to Hashem your G-d, for you have stumbled in your iniquities [בעונך] – “iniquity” refers to an intentional sin, yet the verse calls it a “stumbling block.” But did he really say that? Didn’t Reish Lakish also say: Great is repentance, for [through it] intentional sins are treated like merits; as the verse states, “When the wicked repents of his wickedness, and acts with justice and righteousness, through them [i.e., his sins] he will live!” There is no contradiction; the latter refers to repentance out of love, while the former refers to repentance out of fear. 

Mishnah Berurah 581:25 (on Shulchan Aruch 581:4):

מכבסין ומסתפרין בערב ראש השנה: להראות  שאנו בטוחין בחסדו יתברך שיוציא לצדק משפטינו. ומכל מקום לא ילבש בראש השנה בגדי רקמה ומשי כבשאר יום טוב דיהא מורא הדין עליו אלא ילבש בגדים לבנים נאים.


We launder clothes and get haircuts on Erev Rosh Hashanah in order to demonstrate that we are confident in His kindness, may He be blessed, that He will bring out our verdict with righteousness. Nonetheless, one should not wear embroidered or silk clothes on Rosh Hashanah, as one does on other holidays, so that the awe of the judgement will be upon him; rather, one should wear nice, white clothing.



Forthright and frank, yet respectful and sensitive, I Am for My Beloved: A Guide to Enhanced Intimacy for Married Couples by Talli Rosenbaum and David Ribner will help couples enrich their marital and sexual lives, and maintain passion and intimacy within the framework of Jewish tradition.

To order your copy of  I Am for My Beloved click here:


Thank you for joining us!

If you enjoyed this episode, please help us out and subscribe, rate & review the Intimate Judaism podcast on iTunes. This will help us reach out to many more people who can benefit from our show.

Skip to content