Matchmaker, Matchmaker: Why Playing Cupid's A Bad Idea

Novelist Curtis Sittenfeld‘s Salon essay on disastrous matchmaking got us thinking about the perils of being a Yenta.

Writer Curtis Sittenfeld is a terrible, but indefatigable, matchmaker. As she puts it, “I’ve tried to set up nearly a dozen couples, and with one notable exception, it’s never worked. I’ve unsuccessfully introduced straight and gay people, old friends and new acquaintances, but the one thing they almost all have in common is an apparent aversion to each other.” She identifies two reasons why she can’t stop trying. For one, she’s a hopeless romantic. For another, she wants to be in on the drama.

when you introduce two people, you’re immediately creating a story, and I love stories. Think about it: Whether or not the two people like each other, you’re putting a plot in motion. Either the couple does get along, and that plot continues and expands, or they don’t and the plot quickly ends. In a best-case scenario, the two people fall madly in love and there’s a wedding, which, as any reader of Jane Austen knows, is the best possible way for all plots to conclude. Alas, this doesn’t happen 99 percent of the time, but still, the two people involved — and by extension, I — get to enjoy the questions and tensions that arise as the plot unfolds: Where and when will they decide to meet? Will they like each other? Will one like the other more?

Sittenfeld’s matchmaking misadventures make for a funny read, but for any of us who have tried to play Emma, there’s also the uncomfortable knowledge that the act of matchmaking isn’t purely altruistic: there’s an element of control involved that smacks of ego. On some level, don’t we want to be the one to have arranged things – and by extension, isn’t there often a bit of irrational resentment when things don’t work out? You’re perfect for each other! Why won’t you do as you’re supposed to! my petty subconscious might shout on those occasions when I was unwise enough to attempt connecting friends. In my case, too, I came to recognize that my attempts at meddling with my friends’ love lives was a way of avoiding my own – I far preferred being an asexual fairy godmother to the heroine in my own narrative, to use Sittenfeld’s analogy.

And having been on the other end, in some ways being a friend’s pawn can be deeply uncomfortable; while it’s nice to have someone looking out for you, and great to have someone trusted vetting people for you, it can lead to all kinds of bad feeling. Seriously? you are sometimes left thinking. This is who you think I am? Do you know me at all? Breaking the news to the macher in these cases is not fun. Not to mention the universal dislike of being patronized by those friends in relationships. And the less said about the loathsome Millionaire Matchmaker, the better.

But of course, a success story means it’s all worth it. My dad, amongst other claims (chief amongst them allegedly having invented the “what’s hot, what’s not” list) says he has been responsible for no fewer than four enduring marriages. Now that I think of it, several of my male friends have brokered successful relationships (although it should be said the “matchmaking” seems to have sometimes taken the form of, “dude, if you don’t make a move, I will” type goading rather than subtle foursome dinners.) Tons of couples meet through friends one way or another, and when mutual interest has been expressed, it’s deeply satisfying to put two people in touch. But the fact remains that some of us just aren’t born with the successful matchmaking gene, and for the good of our social lives, like Sittenfeld, we’ve got to know when to cut our losses and rewatch Clueless.