My Hebrew school years at Temple Beth El were predominantly spent in the principal’s office, where Mr. Edelstein would admonish me for various infractions ranging from basic classroom disruption to throwing spitballs on the bathroom ceiling. In his singsong voice, he would say, “Back again, Mr Ginsburg? We should get you your own room!”

Twenty five years later, I received a warm email from a woman inviting me to perform at her Orthodox synagogue in Teaneck, New Jersey. Apparently, this woman’s sister had seen me headline at Caroline’s on Broadway three days prior and had gone home and raved about me. She explained that her sister is hard to impress and that I would be a perfect fit for their shul’s upcoming comedy night. The irony of being invited back to shul and this time be paid to be the class clown was not lost on me. I graciously accepted the gig and was told that my 45 minute performance must be completely clean with no sexual material, swearing, or any other subjects deemed inappropriate for an Orthodox Jewish audience. Far from a filthy comic, I still had yet to perform a comedy show under such strict guidelines. With two rabbis in my extended family and having grown up in a kosher home in a Jewish community in Long Island, I understood the parameters.

After going over my nightclub act, I realized that half of the material would need to be thrown away. I began writing a new act from scratch and studied the old Borsch-Belt comics such as Alan King, Henny Youngman, and Robert Klein. Since my wife had just given birth to our second child in November, I began my act with, “My wife and I now have two boys because we believe white men in this country are highly underrepresented. Next, we’re trying for an Apache female.” I continued on in this fashion until I had written twenty new minutes. I practiced the new material at comedy clubs, bars, and ran all of the jokes by the wife, Rachel, the ultimate litmus test. She is a very smart woman and a tough laugh—a mere smirk from her usually translates to big laughs onstage.

As the show date approached, I received another email—this time from an Orthodox shul in Long Island inviting me to do a show three weeks prior to the engagement in New Jersey. Apparently, the world of Orthodox synagogue comedy bookers is small and the two women were friends. I accepted that gig as well under the same strict guidelines. On the night of the show in Long Island, I ditched my usual stage attire of a black t-shirt and blue jeans and donned the only suit that I own. There was only own problem: to this day, I still cannot tie a tie. This intentional act of rebellion to conform has left me scouring for help at every wedding and funeral that I am forced to attend. While my wife is usually my “tie guy,” at our own wedding, I had to employ a stranger that I approached on the street. As embarrassing as it is, I doubt that I will ever learn nor attempt the intricate undertaking. Rachel finished tying my half Windsor and I headed out the door to Long Island.

When I arrived at the shul, I saw that the show was set up in a large ballroom that resembled a wedding. Roughly two hundred and fifty people sat at numbered tables adorned with floral centerpieces and ate their buffet-style dinner. The stage itself was non-existent—just a little alleyway in front of one of the tables with a microphone stand. The lights were bright fluorescent and I noticed that nobody was drinking wine. I asked one of the congregants why and he informed me that this was a dry shul. When the event organizer introduced me, I opened with the following: “Thank you very much! Wow, look at this! Bright lights, nobody’s drinking, this is gonna be great!” That received a big laugh, and I was off to the races. The material drew consistent laughter although I almost slipped up once, beginning an inappropriate joke and cutting it off halfway with, “I can’t tell that joke.” That too received a laugh and after the show, the congregants wanted to know what the secret joke was that I could not tell. For my own benefit, I kept that one a secret.

The second show in Teaneck was even better as I made small adjustments and entertained a smaller but livelier crowd—-the wine in their glasses no doubt played a role. After the show, the woman who booked me introduced me to her family and thanked me for coming. Everyone was extremely complimentary, in large contrast to Principal Edelstein’s review of my act so many years ago. The opportunity to perform at Orthodox synagogues has made me a much better comedian, and I look forward to the next time my wife has to flip up my collar, work her magic, and send me off to battle.