• האומר אחטא ואשוב אחטא ואשוב

The Mishnah on Daf 85b stated, האומר אחטא ואשוב אחטא ואשוב אין מספיקין בידו לעשות תשובה – If one says, “I will sin and do teshuvah, I will sin and do teshuvah,” he is not given the opportunity to do teshuvah. The Gemara on our Daf asks why the Mishnah needed to state “I will sin and do teshuvah” twice, and answers that this is in accordance with that which Rav Huna said in the name of Rav, כיון שעבר אדם עבירה ושנה בה הותרה לו – Once a person commits a sin and repeats it, it becomes permitted to him. When the Gemara questions whether it could possibly be that the sin is permitted to him, it answers that Rav Huna means אלא נעשית לו כהיתר – it becomes as though it were permissible.

• Halachos regarding appeasing the one that was wronged

The Gemara brings several teachings about the chiyuv to appease a person one had wronged.

● Rebbe Yitzchak said: כל המקניט את חבירו אפילו בדברים צריך לפייסו – Whoever aggravates his fellow, even through words, is required to placate him.

 ● Rav Chisda said: וצריך לפייסו בשלש שורות של שלשה בני אדם – It is necessary to placate him with three lines of three people. Rashi explains that he needs to appease him three times, and each time he is accompanied by three people.

● Rebbe Yose bar Chanina said: כל המבקש מטו מחבירו אל יבקש ממנו יותר משלש פעמים – Whoever beseeches forgiveness from his friend, should not beseech him more than three times. The Gemara says that if the person he wronged died, he should bring ten people and have them stand by his grave, and he should say: חטאתי לה' אלקי ישראל ולפלוני שחבלתי בו – “I have sinned against Hashem, the G-d of Yisroel, and against So-and-so, whom I wounded.”

• When to say וידוי

It was taught in a Baraisa: מצות וידוי ערב יום הכפורים עם חשכה – The chiyuv of viduy is on erev Yom Kippur, with the approach of dark. Rashi explains that this refers to after he has eaten and accepted the laws of Yom Kippur upon himself. אבל אמרו חכמים יתודה קודם שיאכל וישתה שמא תטרף דעתו בסעודה – But the Chochomim said that one should say viduy before he eats and drinks, lest he lose his mind at the meal. Rashi explains that he might become intoxicated at the meal and be unable to confess properly later. The Gemara says that although he said viduy before he ate and drank, he should say viduy afterwards, lest he sinned at the meal. And although he said viduy in the evening, he should say viduy again in the morning, and again in Mussaf, Minchah, and Neilah. The Ramban explains that we confess repeatedly throughout the day, because Yom Kippur is not mechaper until the end of the day, and a person might sin again before then.  

Siman – Gold (Golden Pez Candy Dispenser). The notorious little thief, who repeatedly said he would steal another candy from his friend’s Golden Pez Candy Dispenser and then do teshuvah, had a major turn of heart and beseeched the victim three times with three friends, and said viduy before he joined his family for the seudah hamafsekes.