Reb Shlomo Zalman Auerbach zt'l would encourage shadchanim to do this great mitzvah. He said that this is the greatest chesed you can do for your fellow man. He said he also spends many hours trying to help people find their bashert and get married.
Someone asked Reb Shlomo Zalman for counsel to be able to bear children. Reb Shlomo Zalman said, "The Chofetz Chaim said that doing deeds of tzedakah and chesed is a segulah to bear children."
The man asked which type of chesed should he get involved in. Reb Shlomo Zalman replied that he should care for an orphan child by paying for all the child's spiritual and physical needs. The man replied that this chesed was too hard for him because he didn't have much money. So, Reb Shlomo Zalman advised him to become a shadchan for older singles, to help them get married and build a Jewish home. He said that this is the greatest chesed.
The man accepted on himself this mitzvah, and it wasn't long before he had a son.
Many people say that they aren't a shadchan and they don't know how to do it. They claim that they don't have the sense to come up with suitable shidduchim, and they are afraid that, at times, people might be insulted if they offer a shidduch that isn't appropriate. They say that even if they come up with a good idea, they don't know how to bring the idea to fruition, how to negotiate, and how to overcome the obstacles that often come up in the shidduch process.
Even so, this doesn't mean that they can't be involved in the chesed of shidduchim. There is always something that they can do. For example, if they have a shidduch idea, they can give it over to a shadchan and let the shadchan complete the job.
Additionally, know that you don’t need to be an expert to be a shadchan. Thousands of shidduchim are made through regular people who have good ideas. They give it over to another party, and the shidduch transpires.
Just think about the distress and worry parents endure when they have older children in their home. Think about this, and you will be inspired to do what you can to help them.
Nevertheless, intelligence and common sense is needed. Not every idea that comes to your mind should be spoken. The shidduch must make sense, or someone may likely become insulted. When in doubt, you can always ask a professional shadchan for their opinion.
Here is a recent story of shidduchim, and hashgachah pratis. It occurred this past Tamuz, and came to its happy ending this year, in Cheshvan:
There were two older single sisters, both in their thirties. They took care of their ill father, who needed constant care and help. At one point, the younger sister was involved in a shidduch that seemed promising, and her older sister was waiting to hear good news from her. However, one day, she noticed that her younger sister was subdued. After inquiring why this was so, her younger sister explained that the shidduch fell through due to finances. She said that she only saved up 150,000 shekel to give towards the dowry. Since their father was ill, he would not be able to contribute, and the girl would be responsible for herself. The other side didn't think this would be enough to support the couple, and the shidduch fell through.
The older sister replied that she has 500,000 shekel saved up and is willing to give all her savings to her so that the shidduch could proceed. The younger sister refused to accept this gift. She said that her older sister needs the money for her own shidduch. However, her sister said Hashem can help her get married even if she doesn't have money. "Besides," she said, "I am getting older and don't know if I will get married. At least you should get married, so our family will have a continuation."
The younger sister immediately called back the shadchan and said she had 650,000 shekel, and the shidduch was quickly finalized.
The chasan was very emotional and happy at his engagement, and he called one of his friends in America to receive a brachah and to tell him the good news. He also told him about the older, single sister who so selflessly gave away her half a million shekel so that the shidduch could happen.
The person on the phone replied, "I know an older single boy who is about the same age as this older sister. I don't know who this older sister is, but the story of her mesirus nefesh impressed me, and I think my friend will also be impressed. I will call him and suggest the shidduch.
Indeed, his friend was interested. This friend was wealthy; he didn't need money for a dowry. He immediately took a flight and came to Eretz Yisrael. The process of the shidduch began. The older sister was worried that the issue of money might come up and ruin the shidduch because she didn't have any money. She didn't know the bachur had heard about her mesirus nefesh to help her sister. So, right away, she let the boy know that she doesn't have money. The bachur replied that he knew and heard the story, which is why he was interested in the shidduch.
This shidduch transpired, as well. They just got married now, in Cheshvan. This story teaches us the trait of vitur, because it was her vitur that brought about the shidduch. It also teaches us the way Hashem makes shidduchim. Sometimes, a lack of money becomes the reason a shidduch will transpire! And it is a reminder to keep your fellow single friends in mind. This friend wasn't a professional shadchan, but he had an idea. He tried, and a family was saved and created. The chesed of shidduchim is the greatest chesed one can do.
