Skip to main content

How to Use Your Matchmaking Skills to Help Your Friends Find Love

These three steps will help you do matchmaking right.


Art Credit: Kitchener Photography

It is a truth universally acknowledged that single men and women in possession of good sense are having a helluva time finding a spouse. As I survey the scene from my married yet empathetic perch, the word that most colors the landscape is struggle.

Comedian Aziz Ansari hilariously enacted the problem last year when he appeared on Conan. And as Monica's refreshingly frank and much-needed piece illustrated, the classic hangouts for singles are just not delivering. Burned out by the bar scene or likewise, 75 percent of the 54,000,000 single people in the US have tried online dating. So the traditional means of meeting and dating aren't necessarily working out. I know plenty of people who have found a spouse through these tech channels, but what I’ve noticed about most, if not all, of them is that they went there as a last resort and they are kind of embarrassed that the computer is the beginning of their story together. As a friend to many singles, I refuse to take that slightly disappointed shrug lying down. I want to do what I can to help ease the burden and add a very personal and loving touch to the search. This is a call to the rest of you who are so inclined to put on your matchmaker hat and wear it proudly.

I first began to suspect that I was a natural-born matchmaker in eighth grade. My favorite part of school from then on was character analysis in literature class. I’ve always loved observing and unpacking the complexity of the human person. I’m really glad I married a man who is as into that as I am so that we can have a thousand cheap dates dissecting all of the personalities in our favorite shows. Also, whenever I read a novel or a short story, I try to assign real actors to the roles in my head. “Who would be the perfect fit?” is always the leading question. But more recently as a mentor and stay-at-home mom, I have found that the practical application of these labors of love is carefully considering two friends or acquaintances, setting the scene, then letting them stew.

I'm still basking in the glint of my matchmaking crown jewel: setting my brother up with a stellar woman. Smiling and statuesque, my brother’s match was in my hometown on business. A firework exploded in my brain: She is the woman for my brother. Some time later, I happily discovered that this gem of girl and I shared a mutual friend. It suddenly became possible to set up these two geographically star-crossed singles. After convincing my brother that long-distance was likely to be only a temporary obstacle, he agreed to hop a plane for a Saturday night dinner in another city. It was awfully romantic, especially because I had been gifted from above with the idea of keeping their identities a secret in order to add fuel to the flame. A meeting that otherwise never would have happened has turned into a promise of lifelong love and commitment.

I know, I know. It sounds totally crazy. And I think it partly was! But it worked. There should be no stigma attached to this. Friends-helping-friends-find-love is a great story. All you people persons ought to apply those skills to the good of your fellow man (and tell him in particular to grow up already so he may one day be worthy of the 20 amazing women you know). Here are three basic steps to get matchmaking done right.

01. Approach your candidates.

I recently decided that an effective strategy is to walk right up to someone I know at least a bit about and say, “Hey, are you intentionally searching for a wife/husband? I can help you.” This usually goes very well. Said single person is charmed that anyone even noticed or cared and is typically ready to open up about his or her struggles, hope, cares, and dreams. Once you’ve done this half a dozen times or so, with equal numbers of each sex, you’ve got a great starting point.

02. Play out the hypothetical in your head.

This next step is crucial and takes some imagination. Role-play in your mind what a first date would be like with various combinations. Do they have similar backgrounds or similar aspirations? Will their temperaments complement one another or will they clash? Will their insecurities overwhelm or will they instead disappear in the presence of this wonderfully compatible person? Don’t be afraid to ponder more far reaching questions, too, like whether they will challenge one another to become better versions of themselves. (Do you see how fun this is?) It’s important not to let the high of matchmaking distract you from your dedication to actually finding a match—if it’s a stretch, keep moving onto a different combination.

03. Offer a teaser, but don’t give away the plot.

Tell each party at least an appetizer of information about the other but not much more than that. It is so nice to discover things in person—in real time, in real space, simultaneously. The platonic form of this situation is, of course, the blind date. In the wake of social media and the internet at large, the blind date is all but extinct. But I say we ought to put in a little extra hard work to retrieve this (potentially) beautiful phenomenon. In order to set it up successfully, you must conceal both first and last names and help make the logistical arrangements for the date. You have to get a little creative with some sort of identifying object or reservation title. Assure your nervous friend that you did not choose the date by scrolling through your Facebook friend list and randomly clicking one. Tell him or her that you thought about it a lot and that you genuinely care about his or her happiness. (And make sure this is absolutely true before you attempt to match anyone.)

Once you’ve done the prep work and mixed your friends together, sit back and hope for the best. Go ahead and let yourself savor any success, because baby, you got a stew goin’.