Rabbi Leonard and Rosalie Rosenfeld were among my parents’ closest friends. They met walking down Beach 9th Street to tashlich on the first day of Rosh HaShana early in our Far Rockaway years, and it was an instant match made in heaven.

As the years passed, the relationship expanded to the rest of the family, including grandparents, my siblings and me, and the Rosenfeld kids. We even took vacations together, the kind that create lifelong memories; to Niagara Falls and Moosehead Lake, for example. (I’ll leave the Moosehead Lake story for another column. Maybe.)

In addition to the family relationship, though, I developed a special one with Lenny. (Not that I ever called him that until I was an adult. Before then, calling him Rabbi Rosenfeld seemed too formal, and using “Uncle Lenny,” following the vogue of that generation for adults too close to use honorifics, just didn’t seem right. So I played the son-in-law game until I was finally able to utter “Lenny” face to face since I didn’t have “Grandpa” to fall back on.)

When my father was president of our shul and sat on the front bimah throughout a long Yom Kippur, Lenny was the adult who I, not yet bar mitzvah, sat next to. And the only time I was tovel on erev Yom Kippur was when he suggested that we use the nearby roaring Atlantic surf as our mikvah. (Once was more than enough.)

When Lenny had his heart attack, I sometimes kept him company if no one from the family was available. My payment for this “babysitting” (as we jokingly referred to it) was having several hours of his undivided attention, so we could schmooze about everything, especially Torah and baseball. (Lots and lots of baseball.) He was equally expert in both, as he was in almost everything I was interested in back then.

But I’d like to focus on a conversation I had with him just before Shavuot when I was in my teens (late high school or early college). I asked him whether he thought it would be a good idea for me to follow the custom of staying up learning Torah the entire first night. I vividly remember his answer, which I’m putting in quotes, because although it’s not verbatim, it’s pretty darn close.

“If you’re talking about quantity and quality of Torah learning, I’d suggest the following,” he said. “After yom tov dinner, go to shul, learn for a few hours with a friend — seriously, no chit-chat — and be in bed by 1 a.m. The next day, go to the regular minyan and have lunch and even a short nap, since you went to bed late. And then use the rest of the long Shavuot afternoon for several hours of serious learning until mincha. And I guarantee that you’ll learn more Torah than if you stay up all night, and as many do, sleep away much of the next day.”

I thought I had my answer. But then he added, “Of course, that’s only looking at quantity and quality. If we consider developing a love for Torah, a dedication to Torah, a feeling of sacrificing (so to speak) for Torah, well then, there’s nothing like staying up all night learning.”

While I didn’t realize it at first, there was a subtext in his response. In addition to dealing with the Hamletian to sleep or not to sleep question, what he also was saying, I think, is that life is not binary. It’s not simply yes/no, can/cannot, best/worst, assur/mutar, must/may not. The world and our lives are full of grays. There are times when quantity and quality are your goals, and other times when you have different ones. So analyze the specific situation carefully, and be thoughtful in your decision making, in order to ensure that the result is appropriate in the circumstances.

There was yet another lesson that I also didn’t notice right away. I eventually realized that he never really answered my question. True, he pointed out factors to consider and helped me look at various alternatives. But he didn’t tell me what to do, or even what he thought I should do. Adults don’t let others make decisions for them, he was teaching. Consult others, ask advice, seek information, wisdom, and judgment but ultimately it’s your responsibility to make the decision.

I had a similar experience a number of years ago, when serious end-of-life issues arose with a beloved family member. I called a rabbi with whom I have a close relationship. He was someone whose knowledge, learning, wisdom, judgment, and sensitivity the family member thought very highly of, and whom we had been instructed to speak to in time of need.

After I explained the issues, there was silence on the other end of the phone for a few moments.

I almost thought we had been disconnected, until the rabbi began explaining that as is often the case, the rabbinic decisors did not speak with one voice about the issues I raised. So first he clearly described the different viewpoints and then he carefully explained basic underlying concerns that halacha had, concerns which all decisors agree upon, even if they disagree about how to meet those concerns. And he then suggested various approaches the family could take that would meet the physical and emotional needs of the patient while remaining true to halacha’s concerns.

But he didn’t give a psak, although he certainly had the credentials to do so. He didn’t tell us what to do. Rather, he reviewed considerations relevant to the situation and sensitively made suggestions for us to consider, and implement if appropriate. He too taught me that life and halacha often are not binary, and that one of an adult’s responsibilities is to make difficult and important decisions personally, rather than leave them to someone else.

I wish I could tell you what I did that tikun leil Shavuot night so many years ago, but I simply don’t recall. It really doesn’t matter, though. What I learned in my short conversation with Lenny — the importance of having choices and the personal responsibility of making decisions — was more significant than anything I would have learned, no matter which of the two paths I chose.

And that has made all the difference.