Before becoming frum, I’d never heard of Shemini Atzeret. Yet even a small amount of research showed it to be a holiday of love. Hashem loves us so much that He wants us back for a special chag that doesn’t commemorate any specific event, but is like an intimate celebration with Hashem on a national level.
 
This always intrigued me because all the other chagim commemorate significant spiritual events—except Shemini Atzeret.

Furthermore, the whole idea of Hashem wanting to be with us so exclusively and intimately—Shemini Atzeret holds the same obligations and prohibitions as other chagim: no phones, no computer, no driving, no malacha except cooking (according to the special laws for cooking on chagim), and lots of praying and singing—always intrigued me because Hashem is Omnipotent.
 
In other words, Hashem doesn’t need anything, including us. But despite all our quirks, back-sliding, and contentiousness, He metaphorically stretches out His Arms and grabs us up for a big tight Divine Hug called Shemini Atzeret.

Shir HaShirim
Even a cursory glance at Tanach, mussar books, chassidus, zemiros and piyutim show that Judaism expects a Jew to cultivate a very personal relationship with God. He is constantly referred to as a Father to Whom we are supposed to speak, confide in, confess, and cry out.
 
And love.

For example, Shir HaShirim (Song of Songs):
Once you know it’s an intimate exchange between Hashem and the Jewish people, and once you learn even a little bit of the symbolism behind its powerful metaphors, it becomes a beautiful experience to read and learn.
 
I once had a roommate who came up with the inspiration to do a responsive reading in English of Shir HaShirim, with one young woman reading Hashem’s part and the other reading Bnei Yisrael’s part. After we finished, her hands, still holding the chumash, fell to her lap as she said in an awed voice, “Look at how much Hashem loves us. He just loves us so much.”
 
The inspiring thing about this is that she was just a very normal young woman in the process of teshuvah and still had foot in part of the secular world and was reading in English—and no matter how good the translation is, Shir HaShirim loses a tremendous amount without the Hebrew.
 
Yet the basic message still shot like an arrow into her soul.
 
This is a beautiful piece to read in a quiet moment as a dialogue of love between you and Hashem.

Zemiros and Piyutim
Zemiros and piyutim are also love songs to Hashem.
 
One of the most famous, Yedid Nefesh, is well-known among both Ashkenazim and Sephardim, with a variety of beautiful tunes to accompany it.
 
Just its opening words: “Soul Companion, Merciful Father, draw your servant to Your Will” already demonstrates incredible adoration on the part of the composer. The verses continue with the love and longing only increasing: “Majestic One, Beautiful One, Radiance of the World, my soul is lovesick for Your Love—please, God, please heal her now…” And later, the composer begs Hashem to spread the Sukkah of His Peace over him.
​
Even if one does not normally feel much emotion for Hashem, singing this piyut in a quiet spot can awaken any dormant feelings of the love and deveikut every Jewish soul feels toward Hashem, whether he or she is aware or not.
 
(Here, Yedid Nefesh is used as an example, but you certainly can and should use any piyut or zemiros with which you connect emotionally.)

Verbal and Artistic Expressions of Love
Talking to Hashem, especially praising and thanking Hashem for anything and everything, also awakens feelings of love and intimacy toward Him.
 
Furthermore, this can also be performed according to each person’s soul-expression: In Tanach, we have examples of our greatest people singing, dancing, playing musical instruments, and writing their love to Hashem. And there’s no reason why you can’t also paint or draw your loving feelings toward Hashem.

​In Western culture nowadays, emotions are given short shrift.
 
Many people shove positive emotions into categories like "sappy," "hyper," or just plain "too much." And negative emotions are treated as unwanted vermin to be brushed aside, stamped out, and exterminated as quickly as possible.
 
The Puritan ethic, so good in some ways, has also spread to Jewish observance as an ideal. But it's NOT the ideal.
 
When it comes to Hashem and our relationship with Him, we're SUPPOSED to get all worked up.

It’s well-known that women connect more easily in this way to Hashem than men.

It’s not hard to think of several reasons for this, such as women being more naturally into relationships, the slavish devotion women show more of a tendency to express toward their object of love (not so healthy when directed toward a human being, but very much the ideal when directed toward God), being more verbally and emotionally expressive, and the fact that (as shown by sources such as Shir HaShirim and the piyutim) the Jew takes on a feminine role in the relationship with Hashem—which comes naturally to women, of course, being already positioned in a feminine role.
 
However, we possess hundreds (maybe thousands?) of examples of Jewish men who have definitely succeeded in cultivating an intimate and loving relationship with Hashem since time immemorial, so it’s definitely a viable goal for all Jews regardless of gender or temperament.

The yahrtzeit of Rebbe Nachman ben Simcha and Feiga (1772-1810) of Breslov falls on 18 Tishrei, Wednesday night to Thursday night.
 
The yahrtzeit of Rav Eliezer (ben Yitzchak) Papo (1785-1826), the author of the Pele Yoetz falls on 20 Tishrei, Friday night to Saturday.
 
Free audio classes and English translations of chapters of the Pele Yoetz can be found here.
 
Free downloads of Rebbe Nachman's lessons and stories can be found here.

There is a very interesting Kli Yakar in Parshat Emor which describes the process of how teshuvah is accepted from Rosh Hashanah through Sukkot.
 
It's very inspiring and shows how vital the pre-Sukkot prep and the first day of Sukkot are for the final step of the teshuvah process in which the Jewish People have been involved until now.
 

If you haven't done teshuvah yet or if you would like to give your teshuvah one final shlug, the first day of Sukkot is vital for doing so.
 
As the Kli Yakar says:
 
"....the first day of the [Sukkot] holiday is the first for the accounting of transgressions. Therefore, the establishment of mass teshuvah needs to be done on that very day."

For the link, please click here.
(It's accompanied by lots of photos for easier reading.)
 
Chag Same'ach!

The Kli Yakar reminds us of the classic symbolism of the above-mentioned flora:

The Kli Yakar notes that during the period, which spans Rosh Hashanah, Yom Kippur, and Sukkot, Hashem does not forgive the entire nation at once. Instead, His forgiveness is a gradual process:

While the teshuvah of even one Jew is very precious and powerful, the teshuvah of many Jews together is even more effective and can induce atonement when individual teshuvah cannot.
 
Therefore, the Kli Yakar explains that Hashem orchestrated the spiritual mechanics to enable individual teshuvah to be calculated as mass teshuvah in the Heavenly accounting. And He does so by melding the different categories of Jews into one single unit, starting on Rosh Hashanah.

But why is it actualized on Sukkot?

Because, explains the Kli Yakar, the ten-day period that spans from Rosh Hashanah until Yom Kippur transforms individual teshuvah to the status of mass teshuvah.

And from Yom Kippur until Sukkot, all Jews are (theoretically, anyway) engrossed in the myriad mitzvot involving preparations for Sukkot (like obtaining the Arba Minim and building a sukkah, and meal preparation, etc.).

This constant mitzvah-involvement protects the Jewish people during that time.

The Kli Yakar explains:

Once again, the Kli Yakar demonstrates how Hashem always sets things up for our maximum advantage, all while operating within the laws of His spiritual physics, so to speak.
 
So the ability to have our teshuvah count for maximum effect now, during the time between the Spring holiday of Pesach and the Summer holiday of Shavuot, goes all the way back to the heavy Autumn season of Rosh Hashanah, Yom Kippur, and Sukkot.
 
It just shows how much Hashem really wants things to work out for us.