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Four Steps to Achieve Matchmaking Success (Your Single Friends Will Thank You)

Want to get your single friends to date? Here’s where to start.
amateur matchmaker, matchmaking tips, how to set friends up, blind dates, finding love, help your friends find love, romance, marriage, love, dating, relationships

Photo Credit: Manchik Photography

There are few things that give me more joy than matchmaking. So many of my friends and acquaintances are tired of online profiles and feel like they have met everyone there is to meet. I’m happy to prove them wrong—and maybe change their lives. But because I’m only one person, I’m just as interested in training other should-be matchmakers to help spread the gift of marriage far and wide.

If you’re one of these people, kiss your inertia or inhibition good-bye, and help your friends find love.

Here’s how I started. One year ago, I celebrated my first success—my brother and Verily’s cofounder got hitched. They are now expecting a baby before the end of the year. Game, set, match. Celebratory dance. After that, I wrote for Verily about the ins and outs of matchmaking. To my surprise, strangers started contacting me for help finding matches for them.

Now, matchmaking for your brother and matchmaking for a stranger are two very different projects. This new kind was a difficult proposition, given that I had argued in my previous post that one should only match people he or she actually knows. But I didn’t want to tell these vulnerable souls to turn around and seek help elsewhere, perhaps from some extroverted friend in their life who studies literature? (It’s my belief that such a person is uniquely suited to this kind of thing, but perhaps I’m biased.)

So I began engaging in long conversations over Facebook chat to get to know my inquirers. I ask questions such as, “Do you know your temperament?” “What sort of people have you dated before?” “What do you consider to be a deal breaker?” I keep a spreadsheet with all the men, the women, their locations, and several notes.

My preferred matchmaking method is the blind date because it retains some of the organic chemistry (the only kind I’ll ever study) that makes first meetings so magical. I’ve set up several of these in recent months, and one of them resulted in another wedding already. I don’t charge for this. I only hope that I’ll be invited to the wedding (quite seriously, my favorite thing in the world). Also, it’s a great place to meet new single people that I can add to my list!

The ones that didn’t work out, however, have taught me so many things that I feel compelled to share them here, especially for any of you who heeded my charge last year and donned your own matchmaking hat or are ready to start now.

01. Get started.

If matchmaking sounds like your kind of thing, let your friends know about it. Surely some of them will be able to supplement the list of single people you know. And keep in touch with those whom you hope to match. Maybe someone is moving to a city where you know more people. Give him or her a little time to get settled, and then check in. Ask point-blank if he or she is open to being set up. Talk about how natural and time-honored this is. (It is! Crack open a novel that was written before the Internet, and be convinced of the normality of friends helping friends find love.)

Find out how willing he or she is to drive or catch a train if the match is in a city or two over. Then ask the types of questions that will help you make an educated match: “Are you introverted or extroverted?” “Do you prefer the company of one or the other?” “Which is more important to you, sharp wit or sweetness?” That kind of thing. Physical attraction matters, too. Be sure to find out if that’s a high priority or low priority for either one. Perhaps your Pinterest eye will come in handy here. As in casting a play, sometimes you can tell if two people will work well just by looking at them together. Your imagination was made for this kind of work, so use it.

02. Prepare carefully.

If you’re going the blind-date route, then you’re the point person from the time you suggest the idea to the moment that the two actually connect. That means you have to handle some of the logistics. First, coordinate their schedules. After that, I usually ask the girl to specify any dietary restrictions or aversions. If there are any, I inform the guy and let him pick a place. Offer suggestions if they’re welcome. Next, you need to confirm the time and place with both sides, and think of a way for them to recognize one another at the cupcake shop, restaurant, or wherever. You could do the classic “she’ll have a red rose” thing or come up with a more creative option. Maybe the reservation could be in the name of an author both of them like. What you don’t want is to get a text like, “Hey, I’m a few minutes late, and I think I need a hint. . . . I’m wearing a blue button-down, if that helps . . .” and not discover it for hours because you were at book club. Not that that ever happened . . .

03. Vet the date.

Ask each party to share about the experience afterward. Don’t feel like feedback is obligatory, though. You could consider your work done from the second they’re face-to-face in the café. But if either person is interested in a more thorough matchmaking experience, you’ll want to engage in some analysis of what went well and what could have gone better. For me, this part is crucial because I’m usually setting up people I don’t know very well, and having a chance to look at particular dating instances with him and/or her is extremely revelatory. You’ll have a far better chance of making a better match next time.

04. Try again.

Go back to the drawing board (or spreadsheet, as the case may be), and update your notes. Think hard, and allow some time and space for inspiration to break through. Maybe the best thing would be to suggest a second date with the same person but in a totally different setting. Give advice only if it is solicited. If after a few tries one of your singles says he or she wants to take a break for a little while, honor that. Be encouraging but not pestering, even if the one who’s cutting back is a great guy, and your list is so disproportionately female-filled! Be sure to be a friend first and matchmaker second. Trust is the most important thing that you have going for you.

One of my singles calls me his “fairy godmother” because of the way I suddenly appear (in a chat window) to ask how he’s doing and tell him that I thought of a promising match. I’m charmed by and grateful for that image. It encourages me to stay positive in my quest to see more weddings, and it reminds me that matchmaking is a big responsibility that is also a lot of fun—not unlike marriage itself.