Matchmaker, matchmaker

This is the third of four posts in The Singleness Series. Stay tuned for the fourth one next Friday!


I’m afraid I’m becoming a little too much like my namesake.

Well, Jane Austen’s Emma isn’t exactly my namesake, I suppose. My parents did like the name Emily, but they couldn’t bring themselves to name their daughter Emily Dickinson. For which I’m very grateful. (Not that I don’t get called “Emily” approximately weekly…) Anyway. My mother has a deep love for Jane Austen, a trait I’ve happily inherited. And, much to my chagrin, I’m afraid I also share quite a few traits with this imaginary Emma of Austen’s creation.

But the one that I’ve most recently uncovered? That has been the cause of no little delight and consternation, sometimes concurrently? I love to matchmake. And I came by it very innocently, I assure you. Allow me to explain.

There I was, sitting at dinner with a lovely friend one evening, swapping stories of old boyfriends and our hopes for marriage and the challenges of being wholly satisfied by God and the like. You know, the good stuff. And I asked her, “Anna,* what do you look for in a man?” And without missing a beat, she replied, smiling, “Humility and a dry sense of humor.” And immediately, immediately I tell you, a name popped into my head: George.* It was as if the clouds had parted and I received a message from the heavens. That is George, I thought. That is George exactly. (Okay, I’m getting carried away here. Suffice it to say, it was a tremendous moment.)

And Anna and George are now happily dating.

Now, I suppose I can’t take too much credit here. Perhaps I should be replaying Mr. Knightley’s words to Emma in my mind: “Why do you talk of success? Where is your merit? What are you proud of? You made a lucky guess; and that is all that can be said.” But you know what, Mr. Knightley? It wasn’t just a lucky guess. It had everything do to with the two parties’ self-knowledge, and vulnerability, and courage.

Get that: self-knowledge, and vulnerability, and courage. As we single people navigate the sometimes treacherous waters of dating, I think these three ingredients are key to our flourishing, whether or not the perfect match comes our way. Here’s why.


I was so impressed with Anna’s reflexive response to my question: humility and a dry sense of humor. It was clearly something she’d put plenty of thought into. I imagine she’d dated men lacking one or both of those traits, coming to recognize their importance to her. And I’ve been asking more friends of mine this question ever since. It’s one that many, I find, haven’t considered, or at least don’t have a ready, confident, answer to. Intellectual and generous, one friend texted me a day after I’d posed the question to her. Someone who willingly gives of himself in myriad ways to those around him. I’d encourage you, too, to consider this question, to give it ample reflection.

Even more important to self-knowledge, I find, is knowing what you have to offer in a relationship. What are your strengths, your weaknesses? In what ways are you actively growing in virtue, and what bad habits do you cling onto stubbornly? If we approach dating looking solely, or even primarily, for what we can get out of it, we’ll be starting off on the wrong foot every time. If you love to write, cultivate your letter-writing muscle. It could become a treasured gift to a future partner. If you struggle with impatience, work on it. You may have a hard time forgiving a date who’s often late. Let’s approach dating with a generous heart, knowing ourselves well and refusing to settle for less than what we—and they—deserve.


I’ve known George for a while, and I’ve always been struck by his freedom in discussing dating. He was never afraid to let on to good friends that he was interested in dating. He was quick to share his foibles and missteps with those close to him. He came to me once seeking particular advice, imagining that he could benefit from a feminine perspective. When we have properly-established boundaries, vulnerability is immensely helpful in the dating realm. It’s vulnerability that allows us to say (out loud, imagine that), Yes, I am definitely interested in dating! It’s vulnerability that gives way to confessions of loneliness, or impatience, or waning hope, which can all be a welcome balm to the ears of fellow sufferers.

A friend told me recently, speaking of anyone seeking a partner, you have to allow yourself to be found. Self-consciousness can plague those on the dating scene, I know. But there’s simply no shame in knowing and owning your desire for companionship, and making it known. Ask your friends (i.e. me, especially if you live in Philadelphia) if they know of anyone who might be good for you. Communicate confidently what you’re hoping for. Don’t be afraid to appear available and approachable. Wallflowers may be lovely, but they can’t bloom until they leave comfort behind. Which brings me to…


You want to know about courage? Courage is a man asking for a woman’s number in front of their friends. Courage is a woman agreeing to meet a man’s entire family on their first date. Courage is stepping out into the unknown, well aware of the risk and the potential for failure, but hoping, still, for the best. Courage works wonderfully alongside vulnerability. It pushes that hesitant foot forward, toward that lovely woman or dashing man, to strike up a conversation. It lets the gaze rest just a moment longer, brings a smile that’s wider than before. It’s the moral virtue that ensures firmness in difficulties and constancy in the pursuit of the good, says the Catechism.

The dating world can feel like a fearful place, I know. But courage can help us to cast that fear aside in favor of the good. And marriage? That desire we have for earthly companionship on the way to heaven? For life-giving love? That is very much a good.

So, in favor of that good, I think I’ll keep my unofficial title of matchmaker, and do my best to avoid Emma’s other disagreeable characteristics. I’ll keep calling myself (and you, I hope!) to self-knowledge, vulnerability, and courage. And I hope I’ll get to revel in the pleasure and triumph of many happy matches to come—even if there are some lucky guesses in there.

*names changed for privacy. Obv.





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