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May I push and persuade so that a shidduch goes through? Where does enthusiasm end and pressure begin?ask your rav

The sources cited here distinguish a convinced proposal from pressure, and warn against taking matters into one's own hands through manipulation.

A personal answerThis is an answer given to a particular person in his or her circumstances, or guidance the source itself does not present as a general rule. Check whether it applies to your situation.
Rav Yitzchok Berkovits

The normal path, he says, is reasoned persuasion, not manipulation. In a rare case a posek may permit withholding some piece of information temporarily, but the go-between must not make such a decision on his own.

“The proper approach is one of reason — not manipulation.”

Shana Kramer

She allows active promotion of an idea the go-between sincerely believes in. The line is that one must never use pressure or talk a person into something he does not really want.

“never to use pressure tactics, or to talk someone into doing something they really do not want to do”

Rav Chaim Shmulevitz

He stresses Hashem's part in bringing a match to completion. A person's attempt to speed things up and push them along, he warns, may do more harm than good.

“only to discover that he has caused more harm than good”

the Steipler

He instructed shadchanim to suggest the shidduch and let matters take their natural course. Persuading parties who had already declined to change their minds was not, in his words, part of the mitzvah.

“the mitzvah is to suggest the shidduch, and then allow matters to take their natural course”

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