The SD is passionate about Shidduchim. There is no greater act of kindness and mercy in the world of trying to “make a shidduch.” It demonstrates to the person that they are not alone, they are not forgotten, that they are important and people are concerned. Ultimately, there is no greater mitzva than bringing joy to a person and their family.
In Chaya Sara we see Abraham decide it is time for Isaac to marry. Rather than pick and go look for a wife he sends his servant Eliezer. How strange. Abraham is constantly on the move, yet to find a wife he leaves it to a servant.
The SD would like to chime in. As a parent, there is no more pain in life than seeing a child unhappy, upset, no fulfilled. The pain is not limited to the single person but includes their parents. The SD often says that when he sees a single person, he really sees their parent, sitting around a kitchen table, drinking a cup of tea and tearing their hearts out that their child is alone-not married. So Why does Abraham not do it himself?
The answer is really simple. As a parent, we can do lots of things: pay tuition; send kids to camp, get them braces on teeth and tutors for geometry. The one thing we cannot do effectively is set up or beat the drum for our own child. It just does not work.
Here is where the chesed comes in. Shidduchim requires other people, friends, colleaguues, and even strangers. Shidduchim requires the kindness of strangers. Eliezer needs to do it. It is his chesed. He has a daughter, but he finds another for Isaac. That is heroic.
Shidduchim is both the easiest mitvza and the hardest. It does not require lots of money like charity. It does not require great Talmudic skills like learning. It is a mitzva everyone can do. Its the hardest because it requires sacrifice of time, effort, energy, disappointment. Lets make Shidduchim our project. Always be on the look out. Do something that even a parent cannot do for their child.