How it All Started

Whoever came up with the idea to send kids to more school after a full day of public school clearly wasn’t thinking about the future of the Jewish people. Twice a week, plus Sundays, I was thrust into a carpool along with several other neighborhood kids, schlepped 20 minutes away, and sat in Hebrew school for another three hours. Meanwhile, my non-Jewish friends got to play and just be kids. Going to Hebrew school felt like punishment!

Walking into our Conservative synagogue, the energy was dead. You could feel that no one wanted to be there—not the administrators, not the teachers, and certainly not the students. The only reason anyone showed up was because parents felt obligated to ensure their children attained their rite of passage: a bar or bat mitzvah. After that religious milestone was reached, Judaism had fulfilled its purpose. No follow-up, no meaning, no direction—just a long, exhausting box that had been checked.

After finishing Hebrew school classes and being bar mitzvahed, I had no desire for any further connection to Judaism. Judaism represented nothing positive. Not only did I feel this way, but all of my Jewish classmates in both Hebrew school and public school felt the same way.

Looking back now, it’s shocking to realize how flawed the system was in helping perpetuate Jewish continuity. Everywhere I turn, I meet people with the same story—pushed through Jewish education by parents trying to quiet some voice in their head telling them to “pass on the tradition,” even though they couldn’t define what that tradition actually was. The result? A generation that ran from something they never truly experienced. No wonder the intermarriage rate is over 50%.

So, I swore off Judaism. I built a life. I worked, took care of myself, hustled, dated, and things were going fine. My brother, on the other hand, got married and became observant. I respected his decision but didn’t really understand it. Still, I liked spending time with him and his family.

During these visits, I was exposed to many of the joys of an observant lifestyle. Shabbos lunches quickly became my favorite ritual, drawing me in with their warmth, depth, and the genuine, meaningful conversations that made the whole experience feel alive.

So if my brother had the same exact upbringing I did, how had he made the decision to become observant—while I had no interest?

Still single in NYC, I was trying to stay open-minded. I knew I wanted to marry someone Jewish—that was non-negotiable. 3,300 years of Jewish history was not going to die with me.

So I checked out this class some friends recommended, given by a woman known as The Rebbetzin. Her organization, Hineni, was offering High Holiday services at The Plaza Hotel—but the Rosh Hashanah meals were pricey, and the Jew in me said, “Let’s find a better deal.”

That’s how I ended up at a different organization called Aish HaTorah. The meals were more reasonably priced, so I made my reservation. At the meals, I discovered interesting and intelligent people who were also warm and welcoming. One thing led to another, and I started going to classes at Aish.

Since I was single, one of the classes I took was entitled Love, Dating, and Marriage. During one of the first few classes, a rabbi asked us to consider the following when deciding whether or not to marry someone: “Do you respect this person so much that you actually want to be more like them?” That question hit me hard.

Up until that point, no one in my life had given me any education about dating and marriage. This rabbi at the Aish class in Manhattan had struck a chord in me. That single question—along with a great deal more information from these classes—made me see dating and marriage from a Jewish perspective.

He compared the way secular people date with the way observant people date, and the contrast was stark, to say the least. It just seemed like observant dating made a whole lot more sense and was more likely to lead to a successful marriage. To this day, that rabbi has my undying respect.

As I kept going to Aish classes, I kept meeting new people. Eventually, I was introduced to a woman—someone who would later become my wife.

While she grew up in an observant household and had gone to Orthodox Jewish day schools, she was open to meeting someone who was at least open to the idea of living an observant lifestyle, even if they hadn’t grown up that way.

This was one of the keys I learned at Aish: you must have a common life direction with your spouse. Since I wanted to marry her, I knew I would have to keep growing in religious observance so that we could both be heading in the same life direction.

The kicker of this story? I ended up proposing to my wife at The Plaza Hotel—the same place I had once attended High Holiday services just a few years before.

To me, Jewish observance used to be a pejorative. But it turns out, observant Judaism has given me a better life than I could have ever imagined.

And now I’m here—Choosing the Chosen Life.