SJS: I’m not making sure they get married, we’re discussing dating. If after meeting the person still insists that 21 is not 22 then fine. However, I think that a shaddchan can decide some issues are worth investigating whether or not they are paper issues or not (by lying and getting the couple to go out).
Charlie Brown:
In the case of remission I was not going to say outright before they met, though I would answer truthfully if asked.
I would not do as much as set someone up who would hold a secret like that until after a l’chaim. I try my hardest to ensure that all parties have a Rov and get proper hadracha. If I know someone will try to hold a secret like that until after an engagement, I won’t work with them.