Beginning shidduchim can be both exhilarating and nerve-racking. It requires a deliberate decision to start a new chapter full of uncertainty. The individual embarking on shidduchim may feel anxious and usually turns to those close to him for support and guidance. I want to explore the delicate balance between the individual’s role and his mentors’ roles in decision-making about dating. As a rebbe of boys, I will focus on a boy’s experience in shidduchim, though the same principles apply equally to girls.

Rav Shlomo Wolbe, zt”l, writes at the end of his sefer, Z’ria U’binyan B’chinuch (adapted into English as Planting and Building: Raising a Jewish Child), that a boy should not be told that it is time to start shidduchim if the boy himself does not feel ready. Conversely, Rav Wolbe adds, he should not be discouraged from beginning shidduchim at a younger age (his example is 19) if he says he is ready and wants to start.

These directives from Rav Wolbe shed new light on chinuch in general, and shidduchim in particular. As parents, we naturally want what is best for our children, but as outsiders, we only possess an external vantage point. In yeshivish circles, most boys begin shidduchim at about age 23, as before this, they may lack the maturity or emotional development needed to responsibly undertake the practical, financial, and emotional aspects of marriage and family. On the other hand, it may be unwise to delay dating beyond that age when their peers are already starting to get married. There is a fear that younger girls may perceive them as too old, or that people may wonder if something is wrong with them for delaying dating. These are all valid considerations; thus, most well-intentioned parents and mentors in yeshivish circles advise against dating before age 22 and discourage delaying dating until after age 24.

One of the most important and challenging mitzvos is kibbud av v’eim – honoring parents. The prime examples provided by Chazal (Kiddushin 31b) of honoring parents are feeding, dressing, and transporting them. Although under normal circumstances the need for this is limited, this mitzva comes to the fore with elderly parents who are no longer able to care for their own needs. It can be tremendously taxing for the children to take care of elderly parents. On the physical level, being on call to assist with daily functions can become very time consuming and involve great physical strain. On the emotional level, it can be very difficult to see one’s parents age and decline; a feeling that is exacerbated when needing to help them with basic life functions.

Of course, we all understand that there is a mitzva in the Torah to assist our parents even when it is very difficult. We also understand that we have a basic responsibility to show hakaras hatov (gratitude) to our parents for bringing us into the world and for raising us. This sense of gratitude behooves us to take care of them as they age.

“Yes, she’s a wonderful, tznius girl with good middos who loves to do chesed.” This is your standard response when anyone asks about a potential shidduch.

“Does she have a good relationship with her parents?” the questioner continues. “Let me think…. Yes,” you respond. “Any emotional issues?” the woman probes further. “Hmm…. Not that I know of.” Now the questioning is finally coming to an end, “Is there anything I should be concerned about?” “Um, I don’t think so. She’s the perfect girl for your son.”

You feel relieved you were able to answer all the questions to the boy’s mother’s satisfaction and will hopefully have a part in the success of this shidduch and building a Jewish family. Was this the proper way to respond to these questions? Well, if the answers were honest and gave an accurate description of the girl, then they were okay – although it would have been better if they came across with more confidence and contained examples that illustrated the good qualities you mentioned.

But what if the girl’s strength and passion isn’t really chesed? What if you had to think about how to respond regarding the relationship with her parents since her father is verbally abusive? And the “Hmm…” before the answer about the emotional issues is because she takes anxiety medication, although you are not quite sure why she takes it. What if the hesitation before confirming there are no other concerns is that she has been hospitalized from time to time, but you don’t know the details?

In my original article, entitled “The Search for a Rebbe,” I presented some of the major qualifications one should seek in a rebbe or rav – namely, someone who elevates the individual, takes a deep personal interest in him, and whose words resonate. I would like to elaborate on the final qualification.

There is a misconception among some people today that the ideal is to become a carbon copy of one’s rebbe. Such students may feel that if the rebbe is holier, wiser, and a greater scholar than them – it follows that the student should lose his own identity and model himself completely after the rebbe. This, however, is a serious mistake.

Rav Naftali Amsterdam, zt”l, asked his great rebbe, Rav Yisrael Salanter, zt”l, “How can I serve Hashem properly? If I had the mind of the Sha’agos Aryeh, the heart of the Mesillas Yesharim, and the rebbe’s middos, I could serve Hashem. But what am I supposed to do in my present state?” Rav Yisrael famously responded, “My dear Naftali, you are mistaken. It is with your mind, your heart, and your middos that you are supposed to serve Hashem!” Each individual is created with his own personality and a specific set of strengths and challenges. He has his own unique mission in the world that only he can fulfill. It is tragic when one doesn’t even realize that he has his own personal mission.

Growing up in the frum chinuch system, we have all heard many times about the importance of having a rebbe to go to for guidance. Those of us who went to yeshiva will remember the great reverence in which we held our rebbeim and how hard we tried to build and develop a connection with them. But as life goes on and we get married and leave yeshiva, many of us find ourselves without a true rebbe figure in our lives. Furthermore, a significant percentage of people, even during the yeshiva years, only had a “rebbe” in the sense of hearing a shiur from him, but they did not have a true relationship with that rebbe, nor did they feel comfortable turning to him for guidance. Some individuals may have even felt uncomfortable with the advice they received when they finally mustered up the courage to ask the rebbe a question – so they didn’t continue to pursue the relationship.

In this article, I would like to explore some of the qualifications for a true rebbe. I hope that through defining what type of person to look for, it will become easier to discover that individual.

One Shabbos afternoon, after a short nap, Rav Moshe Feinstein, zt”l, woke himself up and returned to his learning. The rebbetzin pleaded with Rav Moshe to get more sleep, but he refused and said, “I must learn; I don’t want to be an am ha’aretz (ignoramus)!” The rebbetzin turned to their guest and asked, “Would anyone say that Rabbi Feinstein is an am ha’aretz?!” But R’ Moshe insisted that he needed to push harder to reach greatness in Torah.

This is an example of the type of powerful message that many of us heard in yeshiva that inspired us to put in our utmost to become talmidei chachamim and live the elevated life of a ben Torah. The pinnacle is to become a gadol b’Torah, and one has failed if he remains an am ha’aretz. These messages at times are explicit and, more often, implicit. Regardless, they serve to fuel much of the inspiration for yeshiva talmidim of all ages.