When quarantines and lockdowns for COVID-19 began back in March, sales of board games rose dramatically. However, even before the pandemic hit, our family already maintained a large selection of board games on our shelves.During the summer months, in particular, as the hours between lunch and Havdalah stretch out, Shabbat-observant families like ours scramble for ways to entertain small children. There is no option of turning on the TV or driving to the beach. What better way to pass the time than a few matches of Uno or a game of Catan?For my husband and me, making sure Shabbat is fun for the kids has a dual purpose: 1) to make sure they don’t fight or kvetch all afternoon, and 2) to offer us oneg Shabbat.A component of Sabbath observance, oneg Shabbat refers to enjoying physical pleasures on the Sabbath: tasty and plentiful food, clean and fancy clothing, a luxurious nap. “Mah Yedidut,” a popular Shabbat song, tells us, “The rest on Shabbat day is a taste of the World to Come. All who take pleasure in it will merit much joy.” To outsiders, it might seem strange to focus on physical pleasure on the holiest day of the week, but a lot of Jewish practice includes taking the most quotidian and earthly of activities and elevating them to the spiritual level.Enjoying Shabbat treats—culinary or experiential—also makes keeping Shabbat more appealing. Imagine looking back on a childhood of dreary boredom one day every week, where you could do no labor but also had no fun. Upon reaching adulthood, would any young person want to continue keeping Shabbat? (Puritans actually tried this—it didn’t work out too well for them.)In our home, Shabbat is a day to look inward, to study Torah, but also a day for play. But what happens when Shabbat play no longer gives you pleasure?It’s become a favorite family tradition to buy one or two new board games before Passover and Sukkos to enjoy throughout the holiday. These join our roster of Shabbat entertainments in order to keep things novel and exciting. This year, we bought a highly rated game recommended by some friends: Splendor.Initially, the game charmed me. The rules are relatively simple, there are no tiny pieces, and the game takes no more than 45 minutes to play—usually less. When I finished playing our first round of Splendor, I encouraged one of my kids, who hadn’t played yet, to join us for the next round. “So fun!” I proclaimed.My enthusiasm slowly waned. Around my fourth or fifth time in a row losing, I started to sigh after each loss. A month after Passover, I had played the game about a dozen times and not won once.“That’s it!” I told my husband, tears in my eyes. “No more for me!”In both my professional life and my personal one, I've tried to adopt the mindsets of “Step out of your comfort zone” and “Don't be afraid to take a risk.” I regularly nudge students to experiment with writing a genre they have yet to try. Not so long ago, I worked very hard to overcome a crippling phobia. Playing games on Shabbat has been a way to teach my kids to stretch themselves and to keep trying.It hasn’t always been easy. When they were little (and maybe not so little) my children struggled with this lesson. Games of checkers ended with flying game pieces, games of Monopoly Deal ended with cards flung in an opponent’s face. How often was I awakened from my Shabbat afternoon nap by raised voices?I tried to teach my kids by example. When they beat me at Blokus, I praised their strategy. After they trounced me over Catan, I reached across the board and shook hands with them.Sometimes, they asked, “You lost! Why are you smiling?” Invariably, I told them, “Because I enjoyed spending time with you.”My husband knows this about me, knows I’m usually a good sport, so when he heard me swear off Splendor, he wanted to know what had changed.I thought a few moments, then said, “It’s not that I need to win—I need to believe it’s possible to win. I no longer even have hope of winning.”Telling the kids, “I need a break from this game,” we put away Splendor and played 7 Wonders—which I promptly lost.Then we played Catan. I lost.Thinking maybe a cooperative game would be better, we played Mysterium.We all lost.One last ditch effort: After Shabbat was over and we could write again, we played Scrabble, a game that I have never mastered but have far more experience in than any member of the family. My youngest child won, not because she had totaled the most points during play, but because she finished her tiles first and thus received the points on the tiles everyone else had left over.I gave up.Telling myself that I shouldn’t be suffering through one humiliating defeat after the next on Shabbat, I spent two Shabbats refusing to play any games with the kids. Mostly, I lay in bed reading, but occasionally I pondered why a little losing streak got me down. Why? I wondered. Why am I so bad at many games, especially ones that involve strategy? Is my brain broken? And why does it bother me so much?I remembered my sister beating me to the afikoman, beating me in games of checkers. I recalled being the last picked to play games on the school yard, ridiculed for failing to catch a ball. Most humiliating: teaching my 9-year-old cousin how to play chess—I was 19 at the time—and having him beat me on his first try.On some level, maybe I’m still a little girl, losing games to a cleverer sister. Maybe part of my ego is still sitting across the chess board from my brilliant cousin (who is truly a genius and now practices cardiology in Philly).I want to feel smart. I want to feel like a winner.Also, I think, Maybe I enjoyed my dominance over my kids when they were small. Maybe I enjoyed it too much. When they were tiny tots, they looked up to me. Now two have outgrown me, two regularly sass me, and all of them are smarter than I am.But I can still be wiser.Three weeks into my hiatus, I was lying on my bed with a book when my youngest daughter came in.“I’m bored, Ima, and no one wants to play with me.” She had Splendor tucked under her arm. Knowing that I wouldn’t win, I agreed to play. And yes, I lost.While I didn’t exactly enjoy myself, it felt right. She was glowing even as she apologized for beating me. I’d taught my kid that enjoying her company—and giving her the opportunity to win—is as important to me as the chance for me to win.At least I beat her in Monopoly Deal later that afternoon.