In year 2008, The Jerusalem Post published an article by Chananya Weissman, in which he suggested that:
If Jewish singles are expected to make Shidduch Resumes that they give to shadchanim, then shadchanim should make Shadchan resumes, that they give to Jewish singles.
In year 2007, The Jewish Press published an article by Chananya Weissman, where he said:
“Strange as this may sound, the occasional success makes it easy for shadchanim with haphazard methods to pass themselves off as competent, for singles to continue putting their fragile hope and energy into something that depletes them of hope and energy, and for our inertia-laden society to delude itself into believing the system is working pretty well. (After all, it worked for so-and-so.) As a result, change continues to be slow and tentative while the ranks of suffering singles continue to grow.”
In year 2020, Emes Ve-Emunah published an article by Chananya Weissman, in which he criticized shadchanim for abandoning older singles and the poor.
In that article, he also criticized shadchanim for not knowing the people they match, and for not trying hard enough.
In year 2023, Chananya Weissman published an article on his web site, in which he pointed-out that shadchanim are one of the few professions that have no way of removing people who do not belong there.
In the same article, he also pointed-out that we sometimes reward failure by giving more money to shadchanim who do not succeed in getting Jews married; in any normal profession, people who do not succeed would be fired from their jobs, and thereby removed from a profession where they do not belong.
In year 2023, Chananya Weissman published an article on his web site titled:
“What Makes Someone a Good Shadchan?” Three quick quotes from that article:
[1] “It is not the place of a shadchan to admonish people to settle for something that they don’t want. There is a fine line between offering advice and trying to control people, and many shadchanim trample over that line like they own the place.”
[2] “A good shadchan offers encouragement. A bad shadchan offers despair.”
[3] “It’s common for a shadchan to place someone on the front burner when they first meet them, make a haphazard attempt or two to fix them up, and then give up on them when it doesn’t work out. They admonish singles to never give up, yet they give up if they don’t get satisfying results from their initial attempt.”