The shidduch date went well. Like me, Rachel had come to Israel after college. She, too, was a baalas teshuvah, firm in her dedication to Yiddishkeit and building a Torah home. We got along very well, had easy conversations, and she even excused my many foibles during dating, drawing out our first date for more than four hours, not paying for her taxi back to seminary, ang getting us on the wrong bus back from the zoo and ending up on the completely wrong side of the city.

Upon my mashgiach’s advice, our most recent date — number eight — had been long; we’d spent 18 hours together. This was his solution to seeing how the other person handles themselves in many situations. Rather than prolonging dating over several months, he suggests a long trip that wears them down and lets a bit of their true selves come out. So we’d caught a bus from Yerushalayim to Tzfas early in the morning, walked around the holy city of the north, ate lunch there, davened at the kevarim, and bused back for a late dinner. When she still wanted to continue after that, my mashgiach told me straight: “You’re definitely heading toward an engagement. Get yourself ready.”

That shook me. Dating had been fun, but it took those words to cement the commitment I was making to build a home. It’s not about the fun. It’s about determining compatibility in middos and hashkafah to raise the next generation.

I wasn’t scared. I felt ready, and I was confident that we could do it — together.

There we were, in Yemin Moshe. Everything about the setting — the view of the Old City, our fancy clothing, the sense of purpose — felt like it was arranged for the climactic moment when I would bring up the subject on both our minds.

Rachel must have sensed what I was about to say, because before I could, she made a simple-sounding request: “Before going further, I would like you to meet my parents.”

I hadn’t anticipated that. But my mind made a quick shift. That’s not so bad, I remember thinking. This was before the days of Zoom and WhatsApp, so fulfilling her request meant leaving Eretz Yisrael before summer zeman ended and flying to her hometown Bellington, washington in the Northwester US. Not so simple, but not unheard of either.

I arrived home after the date and spoke it over with my mashgiach. Was it concerning that we’d gotten to this point of essentially committing and then having this sprung on me?

The mashgiach had another concern. He worried about Rachel’s commitment to Judaism. Marriage is a big step for everyone, but while for an FFB, it’s about learning to live with another person, for a baal teshuvah, it goes deeper — accepting the responsibility of living a frum life with another person means you’re serious about your Yiddishkeit.

Did her insistence on my meeting her non-frum parents before committing indicate that she wasn’t as serious we’d thought she was? And if yes, should I leave yeshivah without knowing whether she’s really committed?

In his role as my surrogate parent, my mashgiach consulted with Rachel’s advisor and even spoke to her on the phone before letting her take me out of yeshivah. Rachel convinced him of her genuineness and her simple wish to introduce me to her parents.

“We’ll miss you,” my mashgiach told me. “But we’ll see you back here soon.”

The plan was to leave Eretz Yisrael Thursday morning, spend a night catching up with my parents, and then fly out to Bellingham for Shabbos. I would stay with neighbors, eat the seudos together with Rachel and her family, and then return home on Tuesday. My mashgiach advised me to buy a bracelet, the typical gift given at an engagement, and I borrowed money to do so.

The first leg of my journey went well. My parents were happy to see me and hear that I was moving forward with my life. Since I’d already been living as a frum Jew for many years, they’d expected I would get married young. They sent me off to the airport with their blessings, hoping to hear good news — and to eventually meet their new, future daughter-in-law.

On Friday morning, I flew out to Seattle-Tacoma, the closest major airport to Rachel’s hometown. Rachel met me at the airport — with her cousin. I thought that was weird, but then I figured Rachel just didn’t want to drive two hours to the airport alone. The cousin, who was not on the path to observance, asked me a lot of questions, which I answered easily and confidently. I hoped that everyone I would meet that weekend would be equally personable.

They weren’t. When I met Rachel’s mother, I immediately sensed that she was not pleased with me. I learned that her daughter’s time in Israel was already difficult for her, as it indicated that she was taking a different path from the one on which she had been raised. Here I was to ensure that it was for real.

Her father hid his disapproval better. He had grown up in a Jewish neighborhood in Chicago, and was thus familiar with Orthodox Jews, so he had fewer reservations about his daughter’s new interest in Yiddishkeit. However, he was a small business owner, having worked hard to build his company from the ground up, and the thought of his daughter marrying a yeshivah bochur who wasn’t even trying to get a job was too much.

Here I was, jet-lagged and far from home, even farther from yeshivah, and the first impression I received from my future in-laws wasn’t one of excitement and joy, but suspicion.

At least, I thought, I had Rachel on my side.

But as the Friday night meal progressed, I became skeptical. We shared a table with Rachel’s parents, her nineteen-year-old brother, Rachel’s uncle and aunt, a neighbor couple, my hosts, and of course the non-frum cousin. They were all very nice, asked me a lot of questions, but no one brought up anything about Rachel and I getting engaged or even dating. The same thing happened at the Chabad shul where her father and I davened. Many people came up to us, but he didn’t mention to anybody why I was visiting his daughter.Did the woman I’d dated so many times in Israel, and who’d convinced my mashgiach that she was sincere, forget to inform her parents about our planned engagement?

I spent Shabbos in an emotional turmoil.

It could be she was getting cold feet, but I never got the chance to speak it out with her. On motzaei Shabbos, Rachel’s brother took me out for coffee, claiming his sister was tired. The next

morning at Shacharis, the Chabad rabbi, who probably guessed why I was there, pulled me aside and prepped me on how to butter up Rachel’s parents before I could broach the idea of marriage. And finally, that afternoon, when our planned outing to the bay got rained out and we instead walked around the local mall, before I could ask her what was going on, the girl I thought I was pretty much engaged to told me she was having second thoughts.

Now what?

I knew that sometimes Hashem sends hurdles to knock us off course. And my mashgiach had trained us for marriage by teaching us Rav Dessler’s “Discourse on Loving-Kindness.” There, Rav Dessler writes that marriage is about giving — giving your time, giving your emotions, giving unconditionally. I quickly realized that Hashem was giving me a practical lesson in doing just that, even before the chuppah.

I spent the next two days in a whirlwind of constant discussion with Rachel and her parents. I was sure that was the giving Hashem wanted from me at the time. I validated their concerns about adequately financing our home. I explained that I was realistic and practical about the need for balanced integration of halachah and Yiddishkeit into modern life. Late Monday night, I felt I’d allayed everyone’s fears — especially those of my future kallah — and just a week after that pivotal night in Yerushalayim, I pulled the gold bracelet from my coat pocket, and asked Rachel to marry me. She said yes.

It was too late to call my parents — who were three hours ahead of us — but the next morning after davening, I informed my parents, who excitedly “met” their future daughter-in-law over the phone. My hosts took our picture and sent it to them.

And then it was time for me to get to the airport. Again, Rachel’s cousin accompanied us, which bothered me, but I was too happy to have gotten engaged to protest. After all we’d been through that week, it was difficult to part, but I was comforted knowing that we were dedicated to planning the next steps as an engaged couple.

The flight back to LaGuardia was uneventful, but I was restless, excitedly thinking over everything that would follow. I’d turned my phone off when I got on the plane, and now that I had landed, it wouldn’t turn on — the battery had died. Not only could I not call Rachel to tell her I’d arrived, but my friend who was coming to pick me up had no way of telling me he was stuck in bad traffic. I waited for him outside in the heat for almost an hour. When I finally got home, nobody was there to celebrate my homecoming or congratulate me on the momentous occasion. I was hungry, tired, and emotionally drained from my roller-coaster ride of a week. But it was time for Minchah, so I set my phone to charge and went to shul.

I didn’t even stay for Maariv, because I needed to eat, but the Nine Days had just begun, and all the restaurants in my immediate neighborhood only served fleishigs and had closed before sunset. I walked close to half an hour to find a bagel shop still open, and only after eating did I return home.

On that walk back, I contemplated everything I’d been through. Every step had brought out hidden strengths I hadn’t known I had, gifts from Hashem to bring me to the climactic happiness of that moment. But now, I was relaxed, physically and emotionally. I was about to call my future wife.

The house was still quiet when I got back, which I took as a blessing. I could call Rachel without any background noise. I was sure she was worried that I hadn’t called her yet, but there were no messages when I turned it in. That’s strange, I thought. Why hadn’t she called? I sat down on the couch and dialed her number.

“Hi,” Rachel said, rather flatly.

I glanced up at the clock on the wall; we’d parted close to eight hours before. I sensed that she was probably upset that I hadn’t called right away, and I apologized and explained about my dead phone, waiting outside the airport, and having to search for food. “I’m so sorry I didn’t call until now.”

“Oh,” she said, again without expression. I suddenly became acutely aware of the absolute silence — both in the room I was sitting in and from her end of the phone.

This was not how I’d planned this call would go. “Is everything all right?” I asked innocently.

She let out a sigh, which said everything. I didn’t even need to hear her words to know that Rachel was again unsure about our future together.

This time, however, I wasn’t in Bellingham to smooth things over. I tried to reiterate all we’d been through, but she remained in doubt.

After we hung up, I immediately called my mashgiach and told him the whole story.

“Should I send her a gift?” I asked. “Should I go back to Bellingham?”

“Not just yet,” he told me, assuring me that he’d talk with her advisor and see what happened.

My parents and I waited anxiously for close to two whole days  — the time difference between Israel and the West Coast complicated their communication  — not knowing what my future would be. In the end, they were just as stumped. All they could advise me to do was to let it go. If they couldn’t figure it out, what chance did I have? I didn’t ask any more questions. We spoke one last time and said our goodbyes. She said she was sorry, and I accepted.

That was a few days before Tishah B’Av. One of my friends at home told me, “Now you have what to cry over.” But I was too stunned to cry.

A few days later, I attended a bris performed by Rabbi Paysach Krohn. The parents of the young baby were friends, baalei teshuvah who’d met in college and settled in Kew Gardens Hills. Nobody else in the hall knew who Rabbi Krohn was, but I was an annual viewer of the Chofetz Chaim Heritage Foundation’s Tishah B’Av video. Just a few days earlier, I’d heard his public appeal to guys and their mothers not to shun shidduchim with girls older than they were. So while he was alone, cleaning up his equipment, I went over to him and told him that I had been engaged to a woman older than me.

“Had been?” he asked.

“Yes,” I said, and I finally broke down in tears. It all came out, right there in the shul. Fortunately, all the attendees were already in the social hall, smearing spreads on their bagels.

Amid my crying, I asked Rabbi Krohn to daven for my ex-fiancée. “She’s so confused and she needs help,” I said.

“But what about you?” he asked.

Me? I hadn’t been thinking about myself. I believed that I’d been acting correctly all along, doing what I had to do with the right end goal in mind. I would be okay, I’d thought.

It took Rabbi Krohn to point out that I wasn’t. I needed to think about myself and what I’d been through. I used the rest of the summer to figure out what was best for me, and I decided that it was to be back in Eretz Yisrael.

Elul arrived, and I returned to where I’d been before the whole ordeal. But while my learning was going well, I felt a strong desire to start the next phase of my life already. Eretz Yisrael suddenly felt very lonely; the positive environment and the camaraderie of the other guys couldn’t compensate. I made a deal with myself: If nothing happened by Pesach, I’d return to the US and at least be around my family.

One night, I shared a ride on a bus with a rebbi from the yeshivah. That led to a suggestion of a shidduch with one of his neighbors.

“I think you could be matim,” the shadchanit from South Africa who officially redt the shidduch concluded over tea at her house in Meah Shearim. It snowed that night, a rare treat for Israelis, effectively trapping me in Yerushalayim. But precipitation in winter is a good sign here, and I thought it portended that I wasn’t going anywhere else.

I didn’t.

By the middle of Shevat, we were engaged. We got married on Rosh Chodesh Nissan surrounded by family and friends — two weeks before my self-imposed ultimatum.

(Originally featured in Family First, Issue 967)