Finding Your Match: 7 Insights from Rabbi Chaim Kanievsky

Many people approached Rabbi Chaim Kanievsky seeking advice, blessings, and direction in all areas of life.

Usually, the rabbi would briefly lift his eyes from the Gemara, answer in a few concise words, bless the person with “Blessing and success,” and immediately return to learning.

But at times, Rabbi Kanievsky expanded on his answers, offering practical guidance filled with wisdom, sensitivity, and clarity.

Over the years, many of his responses regarding shidduchim, marriage, and relationships were collected in the weekly publication Divrei Si’ach.

1. “The Shidduch Is Delayed. What Should We Do?”

People frequently approached Rabbi Kanievsky asking what could help when a shidduch seemed delayed.

Among the advice he repeatedly gave:

• A young man should strengthen himself in learning Masechet Kiddushin
• A young woman should increase prayer
• Be especially careful with lashon hara
• Avoid speaking critically about others
• Do not hold grudges against anyone

Rabbi Kanievsky particularly emphasized the importance of removing resentment from the heart.

If someone may have been hurt, he advised asking forgiveness directly and making peace sincerely.

Again and again, he returned to the importance of prayer.

“Through prayer, everything can be achieved,” he would often say.

He encouraged people to pray out loud at the end of Shmoneh Esrei, before Yehi Ratzon, rather than only thinking the words silently.

At times, he specifically suggested:

• Praying three times daily with concentration
• Saying ten chapters of Tehillim each day
• Praying for friends who also need a shidduch
• Strengthening oneself in honoring parents

2. How Should Someone Handle Rejection in Dating?

One man once told Rabbi Kanievsky that he felt deeply hurt after receiving a negative answer from a proposed match.

Rabbi Kanievsky responded with a simple but powerful analogy.

“If someone walks down the street looking for Reuven,” he explained, “and mistakenly thinks Shimon is Reuven, would Shimon deserve resentment once the mistake becomes clear?”

Of course not.

Similarly, Rabbi Kanievsky explained, if a shidduch does not move forward, it simply means that this was not the person truly destined for them.

At the same time, he strongly stressed the importance of sensitivity when declining a match.

“You can always find a hundred excuses,” he said. “The main thing is not to hurt another person.”

3. How Much Financial Commitment Should Parents Make?

Financial expectations surrounding shidduchim are often a major source of stress.

Rabbi Kanievsky advised very clearly that people should never promise money they do not actually possess.

“What should someone do, steal?” he once responded sharply.

Instead, he encouraged honesty:
A person should promise only what they genuinely believe they can contribute and explain honestly that they will try their best.

Rabbi Kanievsky also pointed to the many open miracles he personally witnessed regarding marriages and financial needs.

He quoted the Avraham Yeshaya Karelitz, who famously said:

“The greatest miracle today in the Land of Israel is that Torah scholars succeed in marrying off their children.”

4. When Should Parents Begin Praying for a Child’s Shidduch?

People once asked Rabbi Kanievsky from what age parents should begin praying for their children to find good matches easily.

His answer was immediate and decisive:

“From the day they are born.”

5. Should Younger Siblings Wait for Older Ones?

One painful and sensitive question that often arises in families is whether younger siblings should wait for older brothers or sisters before becoming engaged.

Rabbi Kanievsky answered that there is no obligation for a younger daughter to delay her shidduch until the older sibling marries.

At the same time, he acknowledged that ideally the older sibling should marry first, referencing the verse “It should not be done this way.”

Still, when necessary, the younger sibling may proceed first.

6. Should Parents Ask the Older Sibling for Permission?

Rabbi Kanievsky explained that parents are not obligated to request permission from the older child before allowing a younger sibling to move forward with a shidduch.

However, he suggested something emotionally wise and sensitive.

Parents could explain to the older sibling that agreeing gracefully is considered an honor and a merit.

He added that this advice came from his father, the Yaakov Yisrael Kanievsky, who would say that such generosity often brings blessing to both siblings.

7. Can Someone Say One Friend Is “Better” Than Another?

People once asked Rabbi Kanievsky whether it was acceptable, during shidduch inquiries, to compare two friends and say that one was “better” than the other.

His answer was extremely brief:

“Do not answer comparatively.”

Even in ordinary conversation, Rabbi Kanievsky believed people should guard carefully against hurting others through comparisons, labels, or unnecessary judgment.

Wisdom Rooted in Sensitivity

What stands out throughout Rabbi Kanievsky’s answers is not only practical advice, but also extraordinary sensitivity.

Again and again, his guidance returned to the same foundations:
prayer, honesty, humility, guarding one’s speech, avoiding resentment, and protecting the dignity of others.

Even in complicated emotional situations, his focus remained on preserving kindness, truth, and respect between people.