1) Before dating, a person should first look into the prospective spouse’s character and her yiras Shamayim. Rav Wolbe explained that yiras Shamayim is not measured by how long or how intensely a person davens, but rather by how a woman conducts oneself in matters of tznius. Similarly, Rav Chaim Kanievsky said that a girl’s level of tznius is the equivalent of a boy’s hasmadah in Torah learning.

In addition, he would advise that one should investigate whether there are any inheritable medical conditions. The Gemara in Yevamos states that one should not marry from a family with epilepsy, and Rashi explains that this is because it is an inherited illness. This teaches that hereditary diseases are a factor that should be taken into consideration.

At the same time, these matters require the guidance of a competent rav or posek. The Gemara discusses the significance of family history, particularly regarding brothers and sisters in certain contexts, but the practical halachah depends upon the nature of the condition and the medical understanding of its likelihood of being inherited. Therefore, one should present the specific circumstances to a rav or posek, who can determine, in consultation with current medical knowledge where appropriate, whether the condition is considered a halachic concern.

2) The Gemara in Brachos 8a cites the verse that every chassid should daven that, at the moment he is in need, he will find that Hashem has already provided what he requires. The Gemara explains that one interpretation of this refers to finding a wife. From here we see that tefillah plays a role in the timing of one’s marriage. This is the Gemara’s guidance for attaining good timing in finding one’s shidduch: only through tefillah.

In Sefer Igra d’Kallah from the Bnei Yissachar, Matos, on the passuk v’chol isha yodaas, it states that there is a reliable transmission that whomever needs a shidduch should say kapital 121, Shir HaMa’alos Esa Einay, before the yehi ratzon and the conclusion of Shemoneh Esrei.

Another reason for tefillah is found in the Sefer Minchas HaMa’or (Ner Gimmel, Klal Vav, Chelek Beis, Perek 100). He cites the verses, “מה’ יצא הדבר” and “היא האשה אשר הוכיח ה’,” which teach that a person’s spouse is determined by Hashem. Nevertheless, he writes that a person should constantly daven for a proper shidduch, because perhaps, due to his sins, he will receive a spouse according to his deeds rather than according to the ideal match prepared for him.

This is based on the Gemara in Sotah 2a, where Rabbi Shimon ben Lakish teaches that a person’s zivug sheini is given according to his deeds. Therefore, even though a person’s match comes from Hashem, one should continually daven that his sins should not interfere and that he should merit the proper shidduch with Hashem’s mercy.

See further the Chochmas Manoach to Yevamos 63a.

3) The Gemara in Yevamos 63a advises, “Be deliberate when taking a wife.” Rashi explains that this means one should carefully investigate her behavior and personality to ascertain that she is not a bad or contentious woman. The Meiri clarifies that this means she is not quick to anger, but rather easygoing and peaceful. It may be noted that Rav Wolbe said, in his experience, a man’s quick temper is among the most destructive traits in marriage, and a woman’s stubbornness is among the worst, though he added that if it does not bother you, it is fine as well. (In the event that only post-marriage he found that out, the Meiri writes there that he should bear her according to his capacity and leave a place for peace.)

Rav Wolbe would say not to rush because in most cases the determining factor as to whether, how, and whether one’s inner strengths will be brought out is dependent on his wife, as Chazal say, “הכל תלוי באשה.”

The Gemara also offers another piece of advice: “Go down a step and take a wife.” Rashi explains that a person should not marry a woman of a higher social standing than himself, since he may not find acceptance in her eyes. Likewise, Rashi in Kiddushin 49a explains that a wife who comes from a more distinguished background than her husband may consider herself superior to him and conduct herself with haughtiness toward him. We see from this that the goal it is trying to achieve is that the wife should accept you as her husband, long term. That, says the Gemara, can only be if she is able to respect you. Rabbi Wolbe adds that your behavior is the biggest determinant. If a wife sees her husband arising for Shacharis as he should, saying Birkas HaMazon properly, not wasting his time with foolishness, displaying pleasant behavior inside and outside the home, and not being lax in upholding the Torah in private, he can expect his wife to respect him.

4) The Shulchan Aruch rules, based on the Gemara, that an am ha’aretz should not marry the daughter of a kohen, because such a marriage is not expected to end well. The Aruch HaShulchan (Even HaEzer 2:5) explains that this refers to someone who is lacking in mitzvah observance. Accordingly, if a person is deficient in his observance of mitzvos, this halachah may apply.

There are authorities who maintain that the category of am ha’aretz, as discussed in this Gemara, is not applicable in the same way today. Nevertheless, the Steipler (Orchos Rabbeinu) was careful regarding this halachah. However, at minimum, when married to a bas kohen, it is of exceptional importance to bear this in mind throughout the duration of the marriage.

5) In previous articles, the benefits of not approaching marriage from a luxury standpoint were discussed. The Meiri to Yevamos 63a states that this may affect whether his marriage will ultimately succeed or not. See his words.

6) The Chofetz Chaim, at the end of Machaneh Yisrael, in the section entitled Davar Be’ito, discusses the mistake of unnecessarily delaying shidduchim once a person has reached marriageable age. Although the discussion is lengthy, several important principles are being brought down here .

He proves that no human being, not even one possessing ruach hakodesh, is capable of perceiving what Hashem alone knows. At most, a person may perceive matters relating to the present or perhaps the next generation. However, the consequences of a marriage for eternity, the descendants who will emerge from it, and the countless dimensions of compatibility between husband and wife are so vast and complex that they are beyond human comprehension. Therefore, in matters of shidduchim, one should place his trust in Hashem and follow His ways rather than relying on human calculations alone. This is the Chofetz Chaim’s reason against approaching marriage from a luxury mindset.

The Chofetz Chaim further writes that if a daughter has reached marriageable age and is willing to marry a suitable man, yet her parents prevent the match because they feel it is beneath the family’s honor or social standing, they bear grave responsibility. In the case he discusses, the prospective groom was serving in the army, and the parents objected because they felt such a match was beneath their dignity. The Chofetz Chaim writes that such parents will ultimately have to give a דין וחשבון because, by unnecessarily preventing the marriage, they may bring their daughters to sin. He adds that experience has shown that delaying marriage under such circumstances can lead girls to stumble spiritually, רחמנא ליצלן.

Furthermore, the Chofetz Chaim cites the Gemara in Pesachim 113a, which states, “בתך בגרה, שחרר עבדך ותן לה”—if your daughter has reached maturity and remains unmarried, free your Canaanite slave and give him to her in marriage. Today, this would refer to a daughter who has reached marriageable age. The Gemara emphasizes the importance of not allowing a daughter to remain unmarried unnecessarily. It is preferable that she marry even a freed slave rather than remain single.

It should be noted that the Chofetz Chaim was writing in the context of the Russian Empire, where military conscription posed a genuine threat to Jewish young men. Many delayed marriage because they feared being drafted or wanted to secure sufficient financial support beforehand. It was mainly in response to the reality of those concerns that the Chofetz Chaim argues that one should not allow the risk of draft calculations or financial calculations that are not true marriage impediments to postpone a proper shidduch. How much more so, on insistence upon other preferences that are not as great, do his words apply.

The Chofetz Chaim also cites a Midrash in Pesikta d’Rav Kahana (Acharei Mos 27), which speaks critically of eligible young men who could readily marry but choose not to do so, thereby leaving their female counterparts waiting without justification.

7) The Chofetz Chaim, in the last hagahah in Sefer Machaneh Yisrael, writes as follows:

The yetzer hara tempts a person into believing that before getting married he must secure a large dowry [or other preferences] so that he will have what to live on during the first years of marriage. He reasons, “If I receive a substantial dowry, then, baruch Hashem, I’ll be able to support myself for three or four years, even if, G-d forbid, I don’t find work.”

The Chofetz Chaim explains that this is precisely what the verse is addressing: “Cast your burden upon Hashem, and He will sustain you.” What does the verse mean by your burden? And what does it mean to cast it upon Hashem?

The Chofetz Chaim explains with a parable.

A poor man was walking along the road carrying on his shoulder a sack containing two pud—approximately eighty pounds—of grain, together with an additional three litros, another two or three pounds. He met a generous man traveling in a wagon and asked if he could place his load on the wagon. The generous man gladly agreed.

The poor man hurried to empty the extra two or three pounds from the two pud into a small bag, and kept that smaller bag on his own shoulder while placing only the eighty-pound sack onto the wagon.

The generous man looked at him in astonishment and said, “I don’t understand you. If I’m happy to carry the eighty-pound sack for you, do you think another two or three pounds are an issue at all? Put your entire load on the wagon, and I’ll bring it wherever you want.”

The Chofetz Chaim explains that this is exactly the mistake people make.

A man says, “I need a large dowry so that I can support myself for three or four years, even if I don’t find work.” This is not necessarily an absolute condition for marriage, a marriage impediment, but it is a financial calculation—a side preference or need he thinks he needs before deciding to proceed.

We ask him, “What is your plan for the forty-six years after your dowry is exhausted? What guarantees do you have that you’ll keep your livelihood? That you’ll even merit children? Healthy children? That they won’t encounter serious difficulties? That they’ll be accepted into the schools you hope for? That illness won’t strike your family? That you won’t suffer financial loss? That your health will remain sound at fifty, sixty, or seventy? Or even what the world itself will look like decades from now?”

His answer is, “I trust in Hashem that He will provide me with a livelihood, a healthy family, and everything my household will need.”

The verse then responds: If you are already entrusting Hashem with virtually your entire future—your livelihood, your family, your health, and the countless unknowns of the next forty-six years—why are you determined to carry this one small piece yourself? If His wagon is already bearing the eighty-pound sack, why insist on keeping the extra three pounds on your own shoulder? If you anyhow must rely upon Hashem for all the years after your dowry is gone, can you not rely upon Him for another year or two as well?

This is the meaning of the verse: “Cast your burden upon Hashem, and He will sustain you.” Cast the entire burden upon Him, not merely part of it. Since the overwhelming majority of your life’s package must in any case be entrusted to Hashem, it makes no sense to reserve one small portion for yourself. And the verse concludes with an additional promise: if a person entrusts his entire burden to Hashem, “He will sustain you.”

This is one of the ways the Chofetz Chaim teaches us to release our insistence upon preferences that are not true marriage impediments.

8) In the Sefer HaTzaddik Rav Shlomo, p. 37, it is related that the Chofetz Chaim strongly opposed delaying marriage at all. His view was that one should not postpone getting married and that the earlier a person marries, the better.

The Chofetz Chaim also said that even Rav Yisrael Salanter, who said, “Bring me the bachurim, and I will permit them to delay marriage,” made this only under the strict condition that the individual possess exceptional purity of thought, a standard that, unfortunately, is exceedingly uncommon today.

From the standpoint of halachah, however, there is room for a person who is deeply engaged in Torah learning and wishes to avoid interruption to his learning. In HaTzaddik Rav Shlomo, it is brought that the Chofetz Chaim understood that such a person may delay marriage until approximately the age of twenty-one or twenty-two. Rav Wolbe relates that the Chazon Ish would mention the age of twenty. However, in the Chofetz Chaim’s Mitzvos HaKetzaros (Mitzvas Aseh 43), he writes that one may delay until the age of twenty-five.

Rav Avigdor Miller would say the younger the girl, usually the better marriage and building-home material.

9) Regarding the question of how much hishtadlus is required in shidduchim, the Meshech Chochmah, in Parashas Massei, extrapolates from the Gemara in Sotah 2a the following words: “לא יאות בזה השתדלות בזיווג ראשון”—it is not proper to engage in hishtadlus regarding a first marriage, because it was already decreed, “בת פלוני לפלוני.”

This author also heard eid mi’pi eid what Rav Meir Soloveichik related that he heard from the Brisker Rav: that the Brisker Rav said the hishtadlus in shidduchim is only to calm a person’s nerves. Unlike other areas of life, it is not needed in order to bring about the zivug itself.

The author asked Reb Meir Soloveichik if the Gra in Yahel Ohr, page 33, who writes it is in vain all the eisek of people in regards to the zivug, for everything is in the hands of Hashem, etc., is a proof to the above. Rav Meir said he needed time to study it. The author unfortunately never heard his conclusion.

10) The Chofetz Chaim makes another fundamental point. He explains that since the purpose of hishtadlus is not because it is inherently necessary, but because Hashem obligated man to perform it, almost like paying a tax, therefore, since hishtadlus’s effectiveness itself is dependent on it being a mitzvah obligation, it is impossible that Hashem’s obligation of hishtadlus would ever require a departure, even slightly, from the derech haTorah to be part of hishtadlus at all. Not only can hishtadlus never require an aveirah, it can never require acting contrary to the derech haTorah. The Chofetz Chaim writes this in the first chapter of Kuntres Tiferes Adam, where he explains that this is why it is forbidden to shave one’s beard in order to facilitate a shidduch. Such an act can never be considered part of one’s obligation of hishtadlus. Accordingly, anything in the dating process that a person believes he “needs,” but which conflicts with the derech haTorah, cannot be classified as obligatory hishtadlus.

11) The Chofetz Chaim (Sefer Chofetz Chaim al HaTorah, Parashas Shemos) related that he once heard that one of the bachurim in the yeshivah was involved in a shidduch which he felt was suitable for him, but the young lady was not interested. His friends told him that the problem was probably his beard, and that if he removed it with a cream commonly used for that purpose in other yeshivos, the young lady would undoubtedly think more highly of him and change her mind.

The Chofetz Chaim invited the bachur to his home and spoke with him about shidduchim. He then offered the following parable.

Think of a train engine. Attached behind it may be more than one hundred railroad cars loaded with lumber or other heavy cargo. The train must climb tracks leading up a steep mountain, and the mighty engine strains with all its power to pull the enormous load.

Along comes a “smart” onlooker who wants to help the engine succeed. He runs behind the hundredth railroad car and begins pushing with all his strength.

Everyone around him laughs and says, “Do you really think that your tiny push, compared to the tremendous power of the engine pulling over one hundred heavily loaded railroad cars up the mountain, will make the slightest difference? Your strength compared to the engine is like the strength of a mosquito compared to an ox.”

The Chofetz Chaim said the same is true regarding shidduchim. Although Chazal teach that forty days before the formation of the embryo it is announced in Heaven, “Bas Ploni l’Ploni,” Chazal also teach that bringing them together is as difficult as the splitting of the Sea. Therefore, Hashem Himself must attend to the matter.

Nevertheless, a person may suddenly think, “I should help the Almighty. If I shave off my beard, the young lady will be more interested in me.”

The Chofetz Chaim concludes that such a person is no wiser than the “smart” onlooker trying to push the hundredth railroad car with the strength of a mosquito.

12) In the same place, the Chofetz Chaim relates that a man whose daughter had reached marriageable age came to ask his advice regarding a shidduch. A certain bachur had been suggested, but he was only of average stature in his maalos. The father had always dreamed of finding a bachur who excelled in every maalah and every middah, and he asked the Chofetz Chaim whether he should complete the shidduch or continue waiting in the hope of finding someone of a much higher caliber.

It should be noted that this was not a question of personal taste or superficial preferences, such as wealth, yichus, or family background. The father’s preference was for greater maalos and middos in the prospective husband, things that will have a huge impact on the type of children and grandchildren he will have. Nevertheless, the Chofetz Chaim answered with a parable.

Before Sukkos, a Jew seeks a beautiful esrog. It is a mitzvah to beautify a mitzvah, and one should even spend additional money in order to obtain a more beautiful, more mehudar esrog. (See again how those preferences were of a mitzvah nature, not superficial ones.) However, this is only true when there is still sufficient time before Sukkos and one can reasonably continue searching. If Sukkos is about to begin and all that is available is a kosher esrog, then one no longer waits in pursuit of greater hiddur. At that point, one takes the kosher esrog that is available, because allowing the opportunity for the mitzvah itself to pass is far worse than foregoing additional hiddur.

The Chofetz Chaim said that the same principle applies to shidduchim. Once a daughter has reached marriageable age, the perspective changes. Chazal state in Pesachim 113a, “בתך בגרה, שחרר עבדך ותן לה”—if your daughter has reached maturity, free your Canaanite slave and marry her to him.

The Chofetz Chaim is saying that once a girl is of marriageable age, it is already almost Sukkos. [As to why that is so, see the end of Machaneh Yisrael.]

[In the days of Chazal this referred to a girl who had reached the age of bogeres. Today, the concept applies to one who has reached the current age of marriage.]

The lesson is that marriage must be approached from the perspective of necessity rather than preference. Even where the preference involves genuine maalos and not merely superficial considerations, there comes a point at which one must be willing to forgo the additional hiddur in order not to lose the greater objective.

This teaches two fundamental principles. First, marriage should be approached within the framework of necessities rather than preferences. Second, it demonstrates how easily a person can deceive himself into believing that something is a necessity when, in reality, it is only a preference. Third, marriageable age is considered right before Sukkos; there is no more time to insist on preferences.

13) In the book Great Jewish Letters (Artscroll), there is a letter from Rabbi Wolbe in which he writes that during the period when a person is searching for a shidduch, his obligation is to strengthen his bitachon by learning Shaar HaBitachon.

Today, this is readily accessible. There are many editions of Shaar HaBitachon with English translation and commentary, including the commentary of Rav Avigdor Miller and that of Harav Mattisyahu Salomon. In addition, there are many recorded shiurim from them in English available on that shaar. Strengthening one’s bitachon during the shidduch process is itself an important part of the avodah.

14) The disparity between the ratzuy and the matzuy is a vital issue when attempting to create a healthy, normal family. People may have high ideals. Especially when it is not going against their grain, they can be quite on the “frummy” side, where they have habit. Yet, simultaneously, in other areas, many times in the private arena, those very same persons’ behavior is not congruent in their standards of ehrlichkeit and Yiddishkeit, thereby creating a big disparity with such a lower standard in those other areas. How can one expect from his family around him to be normal in the face of such disparity?