On Rosh Hashannah, Yom Kippur and the days in between the Jewish people are doing some major Teshuvah. We stand before our Creator, our Father Above and enumerate our sins, banging our chest in regret for the past and making serious commitments to be better in the future. Our Teshuvah is certainly accepted but this Teshuvah is done out of fear. As the Gemara tells us (Yoma 86b) Teshuvah that is done out of fear has the power to turn our purposeful sins into accidental sins, yet even more powerful is Teshuvah done out of love, love for Hashem. Teshuvah coming from a place of love is able to take our sins and make them into mitzvos.
We are fresh and clean via our Teshuvah out of fear and now we come to sukkos, an opportunity to show our true love for Hashem; the month of Tishrei is like a wedding of our soul to God. Rosh Hashannah is compared to an engagement, where we make a declaration of our intentions to connect with our Divine “Fiancé” – Hashem. On Yom Kippur we are calling out saying, “I can’t believe I lived my whole life without You here! Now I cannot imagine being without You even for a moment!” And finally on Sukkos we enter into the Chuppah with Hashem, under the stars. Even more of an allusion is the seven days of Sukkos are like the seven days of Sheva Brachos. The yearning we felt on Rosh Hashannah and Yom Kippur to come closer to our Beloved God, that new affection we feel for the Torah, for the Mitzvos or just simply the relationship we have with Hashem all culminates on Sukkos when we effectively say “God, I love You, wherever You go I will follow – even to a hut out in the wilderness – as long as I can be with You forever.”
This tremendous love that we sowed over the High Holy days is harvested and brought into the world on Sukkos, and through this powerful love we can come to Teshuvah out of love, where all of our sins are converted into good deeds, for through love anything is possible.