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 