Here is my confession.
I love setting people up. I always have and I probably always will.
The ear doctor just laughs at me and shakes his head whenever I turn to him, wide eyed and (not so discretely) yank my head to indicate someone's flirtation that he should note. His thinks it's silly.
I just get such a thrill out of helping people out. Maybe this is because I'm forever surrounded by engineer guys who I just think are amazing, but sometimes need a little help in the relationship dept.
Anyway, there are a few tried and true steps that I used when attempting to set people up.
Step #1 Finding the Match
Through my experience I've developed some basic guidelines for choosing my set-up targets.
First, background. Nothing is going to work if people can't understand each other's background. I'm not saying that they both have to be from the same hometown, but it does make small talk easier if they have at least been exposed to the other's kind of upbringing.
Second, interests. If I know a guy who particularly loves rock climbing and hiking I'm not going to try to set him up with a girl who gets freaked out by spiders and has no idea what a Nalgene bottle is. While I'm certainly not saying that these two types of people can get together, I've found that similar interests are an excellent jumping off place for the set up.
Third, education. This one is not so hard and fast, but in my experience the best set-ups have come from pairing two people together who have roughly the same educational achievements or aspirations. Different areas of study are often a plus, but there should be an almost equal degree level.
Step #2 Set the Scene
After the targets are chosen, I usually tend to spend one evening talking each party up independently. Causally mentioning to Banana-Replublic-lovin-Mike that Beth and I went shopping there last week. Telling mountain-woman-Lindsay that Chris wanted to go on a hike this weekend. That kind of thing.
Step #3 Deliver the Bait
This is the step wherein I invite both parties over to my house to watch the interaction. I choose my house because it is neutral territory. This way both parties can test the waters without any risk of rejection.
This interlude is critical to the success of the set up. Up through this point it is anybody's guess as to whether or not the sparks naturally take off.
Critical to this event is the interaction. Activities are planned with mingling in mind. I circle the room and make sure that the targets are forced to interact. Sometimes all people need is a little push in the right direction. However, if at any time either party gives the impression that they aren't interested all bets are off and the process returns to step 1.
Step #4 The Follow-up
This may be the most integral step of all. All of the hard work and energy expended in the set up can be undone by skipping this step. How many times have we all met someone, found them interesting and then, for whatever reason, don't ever see them again. This is because there wasn't someone there participating in the follow up.
I call each target separately to thank them for coming to my house and ask if they had a good time. Hopefully they have (you can never tell sometimes). Then, I somehow draw them into a conversation where I innocently mention that the other target looked very nice or did something thoughtful or funny or cool. You get the picture.
Step #5 Butt Out
After Step #4 you remove yourself from the picture entirely. What will be will be. You've helped lay the foundation and created opportunity. Now it is time to step back and let the magic unfold, if it will.