A chain is only as good as its weakest link, or so we’ve been told since we were in second grade. To set a person up with another of your friends requires not only teamwork, but an excellent, watertight plan to prevent complete failure. There are three things to remember when doing any kind of set up:
The first is don’t try to do it all by yourself — consult others. Just because you think someone would be compatible doesn’t mean everyone does. Maybe your friend knows something that you don’t, like person A doesn’t like really tall people, and person B is beyond tall. However, it is also important to remember that not everyone knows everything about your setup subject. Just because you and everyone you know thinks they’ll make a good couple doesn’t mean that the plan is failsafe.
The second is that you should never, never do it without both people being aware they’re being set up. Surprise setups tend to fail because if someone throws a random person you’ve never met before at you, you’re obviously going to resist once you smell the setup — it’s just human nature. On the other hand, these kinds of setups have been known to work here and there, but they can’t be counted on if you want it to work. The best policy is to tell both people ahead of time to make them open to the idea, but if you want to hold them in suspense, give them nothing more than a name.
The third, and most important, is — don’t try to keep people out of your plan. If you insist on not telling one of the parties you intend to set up, when you ask someone to find that person, get that person to go somewhere or if they’re somewhere you need them to be, make sure that person knows why you are looking for them, not that you are just casually looking for them. This is where the easiest of failures can occur, because when someone doesn’t know the plan or why you want something, it becomes simple for them to fail and not even know it.
Besides these three things, there is a great deal more to know when setting two people up. It’s important to not only take into account your own ideas of what two people would be like together, but if their personalities can go together. Does one of them not like people with the same personality as them? Does one not like people who are too different? Do they both loathe setups? And the question any potential matchmaker should ask prior to making matches, maybe even before thinking about any of the other steps outlined here — are they already seeing someone? I have seen many setups that have imploded because someone didn’t bother to check if the other was seeing someone and for whatever reason the other did not say anything.