How to Make a Successful Shidduch
Shabbos Stories | March 17, 2024
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How to Make a Successful Shidduch

Shabbos Stories | June 27, 2025

Shimon had consulted a shadchan to seek a shidduch for his daughter. The shadchan properly assessed that Shimon’s daughter was a solid, average, nice girl with ordinary intelligence and good middos. He suggested to Shimon the names of solid, fine Jewish boys, well suited to his daughter.

For some reason, Shimon kept refusing the shadchan’s suggestions, one after the other, and the shadchan could not figure out why. Months passed. Shimon’s son got married, and it was then that Shimon confessed to the shadchan that his son had known all the candidates suggested and declassified them all as “mediocre merchandise.” Shimon asked the shadchan to raise his standards.

Now it was clear. The girl’s brother had ruined every offer. In his opinion, his father and sister deserved the ultimate young man, the scholar of the generation, without considering what was truly suitable for her.

Waiting for the Other Side to Get Back

Shortly afterwards, Shimon agreed that a suggestion by the shadchan was very suitable and desirable. He waited for the other side to consent, however, they were not yet interested in hearing suggestions. Shimon waited faithfully for this suggestion to pan out – probably on the “expert advice” of his married son.

Months passed; Shimon refused other suggestions, waiting for this hoped-for shidduch. When Shimon heard that this wonderful young man became engaged to another girl, his world collapsed. Thereafter, Shimon became more flexible vis-à-vis suggestions from the shadchan, and therefore agreed to the suggestion of Gershon Levy. He was a ben Torah with good middos, not bad looking but a bit on the heavy side and slightly older.

Shimon realized he knew the boy’s father, who was a wonderful man. Matters moved along swiftly, and before long, Shimon’s daughter was engaged to Gershon. The day after the l’chaim, Shimon spoke to the shadchan, and as an afterthought told the shadchan, “My married son lives a few houses away from you. Would you please go over and tell him we made a shidduch last night? His telephone has not yet been installed.”

The Father’s Deep Disappointment was a Turning Point

The shadchan was astonished that the married son did not know anything about the engagement, and Shimon explained how this had come about: After Shimon’s deep disappointment, he had felt emotionally drained. The suggestion of Gershon seemed so promising, even though he was an older boy, so although he had always consulted with his son before, this time he just hadn’t.

He had asked around and had heard good things, but he didn’t ask his son. Then things moved along so quickly that he simply didn’t have the chance to tell his son about it. The shadchan did not rush to tell Shimon’s son. The next day, after the announcement had been printed in all of the local newspapers, he met Shimon’s 22-year-old son on the way to shul.

The son was angrily awaiting the shadchan and exclaimed, “Did you suggest that overweight guy for my sister? And an ‘alter bachur’ at that? What have you done to my family? What kind of goods have you sold us? If I had known about it, I would have made sure it would never have happened!”

The shadchan did not answer. He knew that this older boy was a treasure, well suited to Shimon’s daughter, and it was only thanks to the non-interference of this young man that the shidduch came about! (There Is No Such Thing As Coincidence)

Shimon’s disappointment with the hoped-for shidduch that never was, overlooking consulting his son about the suggestion of Gershon Levy, the son having moved to a different part of town, and the son’s not yet having his telephone installed, all brought about a destined shidduch.

Reprinted from the Parshas Terumah 5784 email of The Weekly Vort.

Shimon had consulted a shadchan to seek a shidduch for his daughter. The shadchan properly assessed that Shimon’s daughter was a solid, average, nice girl with ordinary intelligence and good middos. He suggested to Shimon the names of solid, fine Jewish boys, well suited to his daughter.

For some reason, Shimon kept refusing the shadchan’s suggestions, one after the other, and the shadchan could not figure out why. Months passed. Shimon’s son got married, and it was then that Shimon confessed to the shadchan that his son had known all the candidates suggested and declassified them all as “mediocre merchandise.” Shimon asked the shadchan to raise his standards.

Now it was clear. The girl’s brother had ruined every offer. In his opinion, his father and sister deserved the ultimate young man, the scholar of the generation, without considering what was truly suitable for her.

Waiting for the Other Side to Get Back

Shortly afterwards, Shimon agreed that a suggestion by the shadchan was very suitable and desirable. He waited for the other side to consent, however, they were not yet interested in hearing suggestions. Shimon waited faithfully for this suggestion to pan out – probably on the “expert advice” of his married son.

Months passed; Shimon refused other suggestions, waiting for this hoped-for shidduch. When Shimon heard that this wonderful young man became engaged to another girl, his world collapsed. Thereafter, Shimon became more flexible vis-à-vis suggestions from the shadchan, and therefore agreed to the suggestion of Gershon Levy. He was a ben Torah with good middos, not bad looking but a bit on the heavy side and slightly older.

Shimon realized he knew the boy’s father, who was a wonderful man. Matters moved along swiftly, and before long, Shimon’s daughter was engaged to Gershon. The day after the l’chaim, Shimon spoke to the shadchan, and as an afterthought told the shadchan, “My married son lives a few houses away from you. Would you please go over and tell him we made a shidduch last night? His telephone has not yet been installed.”

The Father’s Deep Disappointment was a Turning Point

The shadchan was astonished that the married son did not know anything about the engagement, and Shimon explained how this had come about: After Shimon’s deep disappointment, he had felt emotionally drained. The suggestion of Gershon seemed so promising, even though he was an older boy, so although he had always consulted with his son before, this time he just hadn’t.

He had asked around and had heard good things, but he didn’t ask his son. Then things moved along so quickly that he simply didn’t have the chance to tell his son about it. The shadchan did not rush to tell Shimon’s son. The next day, after the announcement had been printed in all of the local newspapers, he met Shimon’s 22-year-old son on the way to shul.

The son was angrily awaiting the shadchan and exclaimed, “Did you suggest that overweight guy for my sister? And an ‘alter bachur’ at that? What have you done to my family? What kind of goods have you sold us? If I had known about it, I would have made sure it would never have happened!”

The shadchan did not answer. He knew that this older boy was a treasure, well suited to Shimon’s daughter, and it was only thanks to the non-interference of this young man that the shidduch came about! (There Is No Such Thing As Coincidence)

Shimon’s disappointment with the hoped-for shidduch that never was, overlooking consulting his son about the suggestion of Gershon Levy, the son having moved to a different part of town, and the son’s not yet having his telephone installed, all brought about a destined shidduch.

Reprinted from the Parshas Terumah 5784 email of The Weekly Vort.

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