Most of the time, a shadchan is particularly invested in one of the parties being set up. They’re not actually setting up pants and skirts. They’re setting up a skirt with their favorite nephew. Or a pair of pants with the neighbor’s aging daughter, lo aleinu.
This manifests especially in the follow-up to the date. The shadchan will call their principal party anxious to hear that it went well. If the principal party is less than enthusiastic, the shadchan won’t push. (S)he’ll apologize instead, and hasten to break the news to the auxiliary party. If the principal party is interested, on the other hand, the shadchan may press a reluctant auxiliary party to try again.
Sometimes, like when a friend sets you up with her cousin, you are not sure into which party you fall. Other times, like when your uncle picks out the best bochur in the yeshiva for you, it’s rather more obvious.
And sometimes you wonder.
Like when your sister-in-law’s brother meets a guy at sheva brachos who he thinks you’d enjoy meeting. You have no reason to assume he’d have anything but the best of intentions and a discriminating eye. After all, you’re best friends with his sister and a sibling of his favorite brother-in-law.
Until you find yourself on the most tedious date of your life with a guy who keeps jerking around to peer over his shoulder (just in case something exciting is about to take place? Does he have insider information?) in between talking with his mouth full about how much he earns.
Was he different at sheva brachos?
Or maybe… maybe his connection to the sister-in-law’s brother is actually closer than you think. Maybe the sister-in-law’s brother is trying to marry this guy off, and for that reason is setting him up with everyone in sight.
Of course, you would never converse with a member of the opposite gender when not dating, so you never have the opportunity to shout “What were you thinking?” at the sister-in-law’s brother. Instead, you politely tell your sister-in-law that you don’t think the guy is for you, but to thank her brother for the thought—it was very considerate and much appreciated.
Yeah, there are dates like that.
The ones that leave you mentally asking the shadchan: Whose side are you on anyway?
Bad for Shidduchim 
If you were willing to actually talk to the “shadchan” himself, rather than pass the information through 8 people, than maybe he’ll get a better idea of what you are looking for and next time around would (hopefully) be a bit more discriminating in who he sets you up with. People need to stop being so caught up in what society will think is “appropriate”, and then maybe, just maybe, the aforementioned “shadchan” may have a shot next time around.
I know my idea is heretical, but that’s the whole point of this blog anyways, right?
(insert smiley face)
That was the story with Greedo. He was set up by a pseudo-relative, she being an incredibly sweet and lovely person, who kept telling me how wonderful he is. If she knew how he behaved or what he said while out with me, I think she would be really surprised.
What is it with these guys who keep it together for everyone else except for a date?
Princess Lea – perhaps they are on their best behavior in general public, but knowing that their spouse will see them as they are act as such on dates. It’s a horrible strategy to have, but I remember reading somewhere (I think The Art of the Date) that some neb tried that with little success.
I also don’t see what the big deal is discussing the idea with the male shadchan over the phone. I can understand why an in person meeting might be objectionable, unless the girl met with the couple at their home and his wife was right there. I’ve talked to a few of ASoG’s friends we set up with a friend of mind or a guy I knew from YU. Playing the telephone game, like MCP said, just isn’t helpful. The few times I’ve tried telling ASoG stuff to relate to a friend about a guy I know, she will almost always express it differently that I would have, which sometimes doesn’t matter, but at others she will convey a very differently nuanced picture of the guy which isn’t accurate.
As a rebbe of mine said in yeshiva in Israel – “If you have a ta’ana on someone, ask them directly!”
Shades – I go by the other perspective: the only person one should be on their best behavior for is their spouse. If Greedo is going to be a jerk to his wife, I don’t have much hope for his romantic future.
Hear most of the points, but to play Devil’s advocate: Perhaps when (and because) a shadchan knows one side well, they feel that the other person should give them time so they can see the same traits, etc., and therefore push it more (and perhaps are right). I’d also say that they push their friend more than you think (at least so I’ve seen).
Also, definitely communicate as directly as possible. If someone is dating to get married, I’d think they’re capable of communicating directly with the person actually trying to set them up (and a person who is married certainly should be able to handle the reverse as well).
That all said, I’ve been disappointed and shocked to hear how friends have acted on dates to the point that I can no longer feel comfortable setting them up. Sometimes, people just seem to turn into real morons on dates. I wish I knew why.
Next time, talk to your sister-in-law’s brother directly!