How To Be A Good Matchmaker For Your Friends
This is about how to be a good amateur matchmaker and not a professional matchmaker...
Matchmakers are not magicians. Matchmakers don't make magic happen. Matchmakers bring together the elements and sometimes there's a spark - a reaction. Many times matchmakers will not be rewarded or even acknowledged - nor should either be sought after.
Love and magic are delicate things. They will happen of their own accord. Magic happens when unexpected - otherwise it's not magic.
Bringing people together is a delicate task and one that carries much responsibility. If handled the wrong way then your relationship to your friends can be affected. So, tread carefully and, above all, listen to what your friends are saying. Beware there is a thin line between matchmaker and meddler.
There are generally two ways you can go about matchmaking: the sly way and the consultative/open way. The method you choose should be based on the preference of your friends. Everyone likes their future partners served up in different ways. Finding the right way to introduce is just as important as finding the right partner to introduce. How you find out your friend's preference is your choice and, most times, a simple question will not be deemed too intrusive - especially if your friend has suggested they are looking for a partner.
If magic doesn't happen the first time you bring your friends together then don't give up. If you still feel there is potential then maybe engineer another "unexpected" meeting. The benefit of doing this "on the sly" is that, if nothing happens, you have not appeared to meddle. Just don't get caught! ;-)
If you are concerned about what your friends think about each other then you could ask "what do you think about so-and-so?" but even that is risky if you are in sly mode and you should definitely leave it at that. Never try and plant ideas into a friend's brain with leading questions like "don't you think s/he is nice?" or demanding statements like "s/he's got a sexy voice!" These will generally cloud the mind of your friend and magic never happens when minds are clouded.
Unless your friend has impaired vision then saying "s/he's attractive" before a meeting can be counter productive. Let your friend make up their own mind. Let the magic happen. Don't appear too meddlesome. And don't go on about how great someone would be for your friend or how great they are - again this will prove detrimental to your goal of getting people together.
If you are matchmaking in sly mode then tell no one else - not even your partner. The worst thing that can happen are sniggers from the background - how off putting.
Before you attempt to bring your friends together please make sure that they are both looking for partners. You may be able to get away with not knowing if in sly mode. But if you are making remote introductions via email or telling your friends that you are bringing them together then it is essential that you have consulted both friends first and that they have consented to being introduced. There's nothing worse than being told to take an interest in someone when that someone isn't interested.
Some other good tips (but there's not much out on the web about this!):