This Sukkot, Don’t Fake the Smile©

Learning to practice joy during Sukkot 2025-5786, when our hearts are still in mourning but hope is on the horizon

Imagine a time when you were happy, but had to feel sad, or a time when you were sad, but expected to feel happy. They are rare instances, but they happen from time to time in our lives.

Judaism asks us to live in that tension all the time. We’re commanded to mourn when our hearts are full, and to rejoice when our hearts are breaking. For instance, it is one of the reasons we break a glass at the end of the Jewish wedding ceremony; to bring a bit of brokenness into the celebration.

I learned this lesson most profoundly during my very first Tisha B’Av at CSK. Our firstborn was born just two days before the holiday where we are commanded to be sad, and to remember destruction. The problem was, I couldn’t get the smile off my face! I was overjoyed because our son was healthy, my wife was recovering, and I was a father. Entering the sanctuary that day, removing my shoes, sitting on the floor, and transforming my smile to a frown was challenging. Years later, I saw the other side. Fourteen years later, almost to the day, on Tisha B’av, my beloved mother tragically passed away. Feeling sad on Tisha B’av that year, and every year since then, has not been a challenge for me.   But I had another, more daunting challenge: Sukkot, the holiday where we are commanded to be ‘happy’. 

When one loses a parent, the mourning period lasts eleven months. It is for this reason that people cannot attend Smachot (joyous occasions) like wedding parties, as they are not allowed to be around that type of joy. But on Sukkot, I could not get away from it. Just a couple of months after her death, I had to sit in my Sukkah, and I was commanded to feel ‘happy’. But what does happiness mean when one is mourning at the same time?  Must a Jew make themselves happy even though everything in their very being is telling them otherwise? 

It struck me later that these two days, Tisha B’Av and Sukkot, are mirror images of each other. Both require us to dwell in fragility. On Tisha B’Av, we sit on the floor, recalling the destruction of our spiritual home. On Sukkot, we sit in a hut that a gust of wind could destroy, rebuilding our spiritual home in the places we live around the world to show that God is still with us. Both are about learning how to live in vulnerability: one through grief, one through joy.

This dance between grief and joy is especially relevant this Shabbat of Chol HaMoed Sukkot. We are still living in the aftermath of the war that began after Hamas attacked Israel on October 7, 2023, but there is much hope. As I write this, the hostages are still not back, but the fighting seems to be quieting down, and we pray that they will be released by Simchat Torah (update: all 20 live hostages have been released by Simchat Torah 5786!).

My own experience of both extreme joy and mourning on Tisha B’av and Sukkot here at Shaarei Kodesh gave me some insight into our Sukkot celebration this year. I’ve learned a valuable lesson on how Jews approach both celebration and tragedy: we do it together. 

On the holiday of Sukkoth, we are commanded to be utterly joyful, or as the Torah puts it, “you shall have nothing but joy” (Deuteronomy 16:15). Rashi points out that the plain meaning of the text suggests that it is merely an assurance that you will experience joy during the holiday season. However, Rashi points out that the rabbis say there is an obligation on the part of the Israelite to rejoice.  How do you legislate a feeling? Perhaps we can reinterpret Simcha for Sukkot in this way. 

It’s no accident that we read Kohelet on Sukkot, the most seemingly ‘joyful’ holiday of all. Kohelet reminds us that joy without reflection is hollow, that even happiness must face the wind of impermanence. The sukkah and Kohelet both whisper: nothing lasts forever, and that’s precisely why we rejoice.

Maimonides adds another layer to our understanding of happiness in Judaism in a section of the Mishneh Torah devoted to the laws of rejoicing on the festivals. He writes that on these days, a person is obligated to be happy and in good spirits: he, his children, and his spouse. But then he defines what that means: joy is expressed through concrete acts, such as sharing good food and drink and giving gifts to each other. 

Maimonides teaches that joy is not a feeling but a practice. It’s not about forcing a smile, it’s about creating joy for others: your family, your guests, your community. We might say today: joy is an action verb in Judaism, and also that joy cannot be hoarded. 

But I was more struck with the second part of the law: one is obligated to feed the converts, orphans, widows, the destitute, and the poor, along with one’s family.  It teaches us that Simcha, in the true sense of the word, meant sharing our sacrifices and our harvest with those around us.  

We are commanded to be joyful, not just with our family and friends, but with the vulnerable: the widow, the orphan, the stranger.  Have you ever been at a party and known that someone was going through a rough patch in life?  More often than not, people tend to leave them alone; they need time. But on Sukkoth, we don't leave them alone, actually, quite the opposite: we bring them in.  Sukkoth has another name, Hag HaAssif, the festival of ingathering.  We are no longer farmers, but we can gather people into our Sukkoth.  

In other words, Sukkot teaches us that joy cannot be hoarded. If someone in our community is suffering, we cannot build our sukkah walls too high. Real simcha extends outward.

Rambam teaches us that Sukkot is about oneness. We are at one with our family, with our community, with the poor, and with the stranger. And when everyone is together, there is likely a flood of emotions. Not everyone is happy.

That’s another aspect of the oneness, Simcha: it is happiness and sadness together.

Yom Kippur is a deeply personal holiday, but Sukkoth begins the process of coming out to each other.  It's a time for us to enter into community slowly through Sukkot, and that can be a bit discomforting.  We literally venture out of our homes into these flimsy huts.  These Sukkoth are supposed to be our homes for the week – and they aren't comfortable.  On Yom Kippur, we afflict our souls, but the work of tesuvah does not end until Hoshanah Rabbah, the end of Sukkot. 

By gathering those who are suffering, we are taking ourselves out of our comfort zone. This too is Simcha.

On Sukkoth, we make ourselves vulnerable to the forces of the world, we admit the realities of the world that Ecclesiastes speaks about, that life is tenuous, that all we are is dust in the wind, and yet we say, nevertheless, we choose life.  

Rabbi Irving Greenberg wisely wrote: Joy is more powerful than sorrow or denial. We are in a new year, but we still deal with the pains of last year. But let us remember that joy is more powerful than sorrow, and there is much to be joyous about. Today is the time of our joy, zman simchatenu. God wants us to be together in one sukkah.

The sukkah reminds us that joy and sorrow can live under the same roof. And when they do, holiness dwells there too. We cannot always choose happiness, but we can choose to act joyously with our community, and in doing so, we often find joy waiting for us.