How to Not Despair in Matchmaking, Part 2

Hodaya asked: “Hello. I’m an older single approaching 30. Although I believe that everything is for the best, I sadly feel that all my prayers and tears have gone to waste — that I’m a lost case and might remain single forever… Each time I go on a date, I’m sure and hopeful that this is it, and then my heart breaks again. Should I keep praying for my match? I’d appreciate words of encouragement and good advice for my situation. Thank you in advance!”

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Hello, Hodaya. Following our earlier discussion, it’s important to recognize the power of prayer in every situation, even when everything feels hopeless and lost.

Your prayer is not a “vain prayer”

The Mishnah teaches that one should not pray a tefillat shav (a vain prayer): “One who cries out about what has already happened — this is a vain prayer. How so? If his wife is already pregnant and he says, ‘May it be His will that my wife give birth to a son,’ this is a vain prayer. Or if he is on the road, hears a cry from the city, and says, ‘May it be His will that those not be my household’ — this too is a vain prayer.” (Berakhot 9:3)

Similarly, the Rambam rules about praying to increase one’s assets after already measuring them precisely (Laws of Blessings 10:24).

A vain prayer is a prayer against an existing reality, because, aside from rare cases of the greatest saints like Rabbi Chanina ben Dosa or Rabbi Shimon bar Yocḥai, God generally conducts the world through natural order.

Painful as your situation is, your prayer is certainly not a vain prayer. Many women marry later, in all kinds of circumstances. Those cases themselves should strengthen you to keep praying and to believe that you too can merit salvation.

Indeed, the decree you’re facing is hard — our Sages said, “A person’s match is as difficult as the splitting of the Sea” (Bereishit Rabbah). Every successful match is a kind of miracle from Heaven. However, that does not mean you should give up on prayer.

King Chizkiyahu (Hezekiah): When a decree seemed final

Tanach tells of King Chizkiyahu, upon whom a death sentence was decreed because of his sin: “In those days Chizkiyahu fell mortally ill. Yeshayahu son of Amotz the prophet came to him and said: ‘Thus says the Lord: Set your house in order, for you shall die and not live.’” (Malachim II, 20:1)

Chizkiyahu saw he was gravely ill and near death; the prophet Yeshayahu informed him of Heaven’s decree in unequivocal terms. Who among us wouldn’t despair if a prophet of Israel proclaimed such a decree upon us?

Yet Chizkiyahu said: “This is what I have received from my ancestors: even if a sharp sword rests upon a person’s neck, he should not prevent himself from seeking mercy” (Berachot 10a).

True to his name, Chizkiyahu strengthened himself to believe in God’s boundless power. Even in his dire state, he prayed, and shortly thereafter the prophet returned to tell him that, due to his prayers, he would live another 15 years.

Through this story, God teaches us never to despair, as we say in the High Holiday prayers: “Repentance, prayer, and charity avert the severity of the decree.” Prayer can sweeten or even break, the harshest decrees.

In moments of discouragement, tell yourself that in these very prayers you are fulfilling your Father in Heaven’s will. See it as a mitzvah assigned to your soul as a spiritual rectification — its eternal reward recorded in Heaven for your good. Also trust that prayers are preserved forever in your “spiritual account” above; through them, God lightens your present pain and brings your future good closer.

Some practical guidance for shidduchim (matchmaking)

1) Regularly “recharge” your spiritual batteries.
Try to watch Torah lectures and attend classes consistently, and look for ongoing shiurim in your area. God likens His word to bread: “Man does not live by bread alone, but by everything that comes from the mouth of the Lord” (Devarim. 8:3). Just as we must eat daily, we must also fill our spiritual battery daily to strengthen faith and face life’s tests.

2) Train yourself to notice the positive — and give thanks.
Look for what’s good in your life and appreciate the many free gifts you’ve received of sight, hearing, smell and taste, hands and feet, parents, health, food, a roof over your head, friends, and countless “small” blessings we enjoy each day without thinking. Most of us are blind to the abundance surrounding us.

Break that habit and thank God each day for His gifts. If that’s difficult, begin by thanking people — your parents for their care, and even strangers whose work benefits your life. Make “thank you” a frequent phrase, said with understanding that without others’ kindness your life would be harder.

Our Sages said: “One who denies a friend’s kindness will in the end deny the kindness of the Omnipresent” (Midrash HaGadol, Shemot 8). Hence honoring parents is likened to honoring God (Kiddushin 30b), and a special directive to husbands: “A man must honor his wife more than himself and love her as himself” (Rambam, Laws of Marriage 15:19). Gratitude is a foundational trait to engrave in the soul. As you become more positive and appreciative, it will naturally draw you to praise God, and, measure for measure, open gates for greater blessings.

3) Make thoughtful hishtadlut (effort) in shidduchim.
“Salvation comes through many advisors” (Proverbs 11:14). Seek good guidance from rabbis, teachers, and trusted friends, on how to improve spiritually and practically. Identify traits to strengthen (honoring parents, acts of kindness, humility, etc.) and learn from talks and books on dating and marriage. On the practical side, tasteful personal presentation within modesty, contacting additional shadchanim, and most importantly, stay open to a broader range of suggestions and circles you haven’t tried. Don’t reject proposals reflexively out of habit or fatigue. Out of millions, you need one man — the right one for you.

Treat each suggestion seriously; people are not factory products. Each person is a “world entire” (Mishnah Sanhedrin 4:5).

At the same time, protect your heart by lowering premature expectations. You’re not a prophet and you can’t know when the true match will arrive. Reframe each date as a small “outing” to meet a new person and broaden your horizons — another step toward your real match. Let life unfold without heavy expectations.

Don’t be “heavy” or downcast on dates, as pessimism naturally repels. If you like yourself, others will be inclined to like you, as “As water reflects face to face, so the heart of a person to a person” (Proverbs 27:19).

May these ideas help you strengthen yourself through hard times. Keep praying for your match with faith; do not despair. May it be God’s will that you find your destined partner soon.