Reuven sinned by rearranging his father’s bed and placing it in his mother’s tent instead of leaving it in the tent of Bilhah where Yaakov had placed it after the death of Rachel. His sin was so severe that the Torah considers it as if he committed adultery (see Gen. 35:22 in Rashi and other commentaries). The Midrash (Bereishit Rabbah 84:19) says that Reuven did teshuvah by fasting and wearing sackcloth. Consequently, he was saved from a decree of death (Shivlei Haleket 18).
The First To Do Teshuvah
The Midrash (Bereishit Rabbah ibid) says that G-d said to Reuven “No man ever sinned before me and did teshuvah. You were the first to do so. I swear by your life that your descendant [the prophet Hoshe’a] will be the first to exhort [the Jewish people] to do teshuvah.” As the verse (Hoshe’a 14:2) says, “Return, O Israel, to the L-rd, your G-d, because you have stumbled with your sins.” The commentaries wonder why Reuven is considered the first to do teshuvah since (as mentioned above) Adam and Kayin had already done teshuvah. In addition, Hoshe’a was not the first one to exhort the Jewish people to do teshuvah as Moshe had already done so many centuries earlier (see Deut. 4:30 and 30:2 and in many places).
Holy Sins
The Kotzker Rebbe explains (Emet Ve’Emunah ot 6) that Reuven’s repentance was the first that was done for a sin committed with holy intentions. The Talmud (Shabbat 55b) says that Reuven rearranged his father’s bed in order to honor his mother as he felt she had been slighted by Yaakov’s moving his permanent dwelling to the tent of his handmaiden (Bilha) rather than Leah’s. Thus, in his mind, Reuven’s sin could be considered a mitzvah. Adam and Kayin, on the other hand, had both committed sins that were clearly sinful. When one commits a sin with holy intentions, it is more difficult to do teshuvah as one can excuse himself by saying that the sin was for a good reason. Reuven was rewarded for his teshuvah by having a descendant who exhorted the Jewish people to do teshuva for the sins they committed with good intentions as he said, “Return, O Israel, to the L-rd, your G-d,” meaning that we should return even for sins committed for the sake of “the L-rd, your G-d.”