MSS,
I have NEVER pressured or even in any form subtly convinced any single to continue dating once they say the word no ONCE!
Maybe that’s why so many of your shidduchim prospects need to go out with 100 people.
Someone just told me that she redt a shidduch to her nephew. The girl said no after a few dates. The shadchan convinced her to speak over the inyan with a mentor, who convinced her that her issues were not substantive enough to call it off yet, and she agreed to give it some more time.
They are now B”H happily married.
There are very many such stories.