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The Rules for Setting Up Your Friends
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Base the matchmaking on prior knowledge of the pair. A casual meetup is a better venue than the one-on-one date, so if you can lessen the pressure by inviting the two to the same outing, then you may not need to do any networking among them at all. If things click when they're introduced, your job is done! If not, then perhaps you can revisit the issue with each of them alone later. But don't press the issue - let it go if it seems one of the parties shuts down the idea of going out with the other party each time it's mentioned. Don't put on a full-court press after the date, either. It's courteous to follow up with a casual, "So how did it go?" but pressing for intimate details is a no-no unless they're offered to you. Consider putting yourself in their place when pairing up your buddies, and you should be just fine.
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