Normally when people this of matchmaking, they think of yentas, overly-involved mothers, dowries, and nightmarish blind dates. Which stereotypes, like all stereotypes, are partly grounded in truth. But I think our culture has been deadened to the possibilities of the art of matchmaking by endless accounts and angry diatribes of gratuitously liberated professional women in their mid-30s screaming "I'm happy being single, leave me along already!" Which is fine, if that works for them. No one should have to suffer through 15 years of well-meaning friends and family members setting them up with guys who are just so sweet and, well, he's a little bit awkward but he means well and he has a good job, so just give him a chance, okay? If she's happy, leave her be.
But what about the rest of us?
Case in point: I go to lots of weddings. Lots and lots of weddings. I love weddings. But how many times have I been seated at a table entirely composed of single girls, or, alternately, a table full of people that I already know really well? I mean, hello! Earth to the bride - your new husband has brothers/cousins/friends/frat brothers/cousins' frat brothers who are dressed in snappy suits and looking great, I just spent an hour doing my hair and I'm wearing a new dress and shoes that hurt, and everyone's liquored up, dancing, and having a good time - you will never have a better opportunity to have young, single, hormonally-driven people meet each other than at a wedding reception! So why, why, why must I sit with my friends (whom I love, don't get me wrong) for 3 hours while I awkwardly attempt to catch the eye of the dude 3 tables over who had the cajones to wear a purple shirt with a silver tie and who, therefore, I could potentially consider as manly enough to deal with the likes of me? If I wanted to date any of these people at my table that I know, I would be doing so already!
Matchmaking doesn't have to be in-your-face, and it doesn't have to be well-organized. In fact, it doesn't even have to be known to be taking place, especially if your single friend is the type to get very flustered and do things like get drunk too fast and/or say embarrassing things in an attempt to be funny and/or go hide in your bedroom closet, where she may or may not end up crying into your old stuffed animal collection. Let's not analyze the reasons why your poor sobbing friend is single, since, as you hear warbling strains of Yesterday floating down from some corner of the second floor, they are perhaps more obvious than anyone would like to admit. Nor should it be a double date with you and your long-term chum/hubby - in fact, it shouldn't be, unless your friend is the type who needs to be dealt with in a manner containing all the subtlety of a hammer to the face. No, no.
Just throw a casual party, make sure there's wine and beer, and some good (not classical or light jazz) background music to kill the awkward silences. Invite a friend or two who is good at talking and gregariously outgoing. Once Potential Guy and Potential Girl have eased into the atmosphere a bit, introduce them to each other. Get them talking. Then scat. If they wander apart, try again a bit later. Then stop trying. Sometimes it just won't happen. But if you can find a way to get them in contact in the following days, say by email, or a Facebook message about "Hey, weren't you guys talking about swing dancing the other night? A colleague of mine goes to this club for the lessons on Fridays and I was thinking about going - have you heard of it?" by all means, do so! If they were smart and/or savvy enough to have gotten someone's contact information during the party, they probably wouldn't be single, and you wouldn't have had to go through the effort in the first place. Help a brotha out, yo.
Now, doing this too often is called being a pain in the ass. But every once in a while is totally called for. Especially in our modern age of tweets, texts, Facebook, and hook-ups, it has become almost impossible to meet an unknown person of the opposite gender and engage them in conversation long enough to learn more about their personality than she drinks Heineken. Seriously people, for all y'all who've been lucky enough to be self-made in this department, extend a helping hand to your old buddy who's just such an awesome person, I can't believe he/she is still single! What's wrong with this world?
And for the love of Pete, have some foresight when organizing your wedding tables. You shouldn't be the only ones celebrating when the clock strikes twelve.