I was all set to move forward, but my kallah had second thoughts

I anticipated that the ninth date of a good shidduch would change my life forever, but not in the way it did. It was a Monday night, and Rachel* and I were sitting on a bench in Yemin Moshe, overlooking the Old City walls. In the back of my head, I could hear my mashgiach’s words, “After this many dates, you’re definitely heading toward an engagement. Get yourself ready.”

I was ready, I thought. I was 22 years old, thriving in yeshivah in Eretz Yisrael. Getting to where I was had been a challenge — after spending a summer with religious cousins nine years earlier, I strove to keep halachah despite my parents’ opposition. In the ensuing years, I’d woken up daily before dawn to daven before school, bought and made my own kosher meals, and hurried by mass transit every Friday after school to my cousins for Shabbos. Now I was between college and career, finally able to immerse myself in a Torahdig environment.

In addition to the worlds of Torah that were opening for me and being in the company of great rebbeim who were dedicated to assisting us in every way possible, it was my first time being among like-minded young men, all seeking to grow in a positive direction. My connection to Yiddishkeit propelled me to new levels, and I felt like after having given up so much for Hashem, it was time to take the next step on my upward journey.

In my mind, marriage was that step. Many of my yeshivah friends — ten that year! — had gotten engaged and married. I thought that if these guys were frum for much less time than I had been, and yet they were making serious commitments to build their new homes on Torah, then I was certainly ready.

So when a friend from college, who was also learning in Eretz Yisrael at the time, suggested Rachel, I said, “Why not?”

I gave my friend a few references, including the mashgiach of my yeshivah, and eagerly awaited what would come next.

What came next was a stern lesson from my mashgiach, who didn’t think one should enter shidduchim because “Why not?”

As the mashgiach in a yeshivah geared toward baalei teshuvah, he was acutely aware that many of his talmidim’s parents were not capable of navigating the shidduch process for them, and he tried to be there for them at every stage. Moreover, he gave daily shiurim in the hashkafah of marriage to prepare us even before it became relevant. He was very disappointed that I had never discussed my interest in marriage with him.

“I hadn’t really thought about it,” I told him. “But then this came up.”

My answer did not satisfy the mashgiach. Now that I was already “involved,” he agreed to make inquiries into the young lady for me, but his shmuess shaped my view before entering this new stage. After a week, he gave me the green light to meet Rachel.