How To Play Matchmaker

Sometimes, you really want to set your single friends up with each other. But how to do it in a way that’s not awkward? And what if it backfires? Today, we answer these questions and more.

Go ahead and do it.

I’m noticing that “do it” is often the first step of a Social Minefield, because a lot of the time the hardest part of the social situation is just marshaling your courage and jumping into it. I talked to psychologist/psychoanalyst Dr. Barbara Chasen, whom The New Yorker once called “New York City’s foremost Jewish feminist matchmaker” (she has since, she emphasizes, retired from the business). When I asked her how people should proceed if they’re interested in setting up their friends, she replied,

They should do it. Most people are shy about doing this, but it’s very nice. […] I think it’s a very loving gesture for friends to do.

This is especially true if your friend has asked for your help with dating. If he or she hasn’t, tread carefully. Just as people can be shy about matchmaking, singles can be reluctant to voice that they’d like to be set up. But some people adamantly don’t want you to do this — maybe they don’t want to date right now, maybe they’d rather keep their friends and their dating life separate, or maybe they’re just wary of the inevitable weirdness if their friend sets them up with someone they find unattractive (“this is what she thinks of me?”) So you’re within your rights as a friend to bring the subject up, but give your prospective matchmake-ee an out — something like, “I totally understand if you’re not into this, but…” This will give your friend an opportunity to shut things down if she doesn’t want you meddling in her love life. But if she does …

Don’t overthink it.

When I asked Dr. Chasen what qualities she based matches on, she listed broad categories like whether the people in question wanted kids. She didn’t talk about hobbies, taste in music, or even personality. Matchmaker Danielle Cenker of JRetroMatch.com concurs, to a point:

Start with the basics. Are they in the same age range? Do they have the same interests? Same professional aspirations? Once you have the basics in order, then it just comes down to personality and that “special something” that makes it a good match.

You don’t want to set up someone who wants kids soon with someone who can’t stand them, or someone who wants to live in the woods with a committed urbanite. But beyond certain deal-breakers, you don’t really know who will click with whom. And your idea of who’s perfect for your friend may be completely different from his. So if you know two people (or more, if you’re attempting the extremely advanced poly setup) who are nice and looking for roughly the same thing (i.e. a relationship, not a relationship, marriage and kids, etc.), go ahead and introduce them. If they like the same ice cream or read the same books or had the same nickname in high school, or if you just kind of have a good feeling about the two of them together, so much the better. But don’t wrack your brains trying to predict if your friends will like each other — only they can figure that out.

Manage expectations.

One of Dr. Chasen’s tips for matchmakers: “don’t expect too much.” Most dates don’t lead to relationships. And many setups won’t even lead to a date. So don’t assume that the friends you introduced are going to get married, and don’t be disappointed if they don’t. Also, while it’s totally fine to talk them up to one another, let them know you understand that any setup comes with a degree of uncertainty. “I’ll introduce you and we’ll see what happens” is way better than “I know you’ll love each other.”

Pick the right venue.

This is also a tip I find myself giving in a lot of situations, but it’s especially important here. Cenker says your choice of setting “definitely depends on the people you are setting up.” She elaborates,

If the people involved are more on the casual side, or if they are not comfortable with going on first dates, then it may be best to have them meet at a party or something like that. If they are used to the dating scene and prefer a traditional “dinner and a movie,” then obviously that would be the way to go.

I know people who’ve gone on blind dates and enjoyed themselves, but I tend to think of this form of setup as a little intense. The party introduction is the other end of the spectrum — very laid-back and informal. This one is great because it’s unobtrusive and doesn’t even really seem like a setup at all. However, if your friends are a little shy or not great in group settings, you might consider a middle option — just hanging out with the two of them, perhaps with one other person around as a buffer. Maybe pick an event you can discuss over drinks afterwards — something that lifts the air of awkwardness surrounding a setup and provides fodder for conversation. Your goal is really just to get your friends talking — they can take it from there. Speaking of which …

Step back.

After the fact, it’s fine to ask your friends (separately, of course) if they’re into each other. But if the answer is yes, try not to be too much of a gossip — they can reveal their feelings to each other in their own time. And don’t butt in with the scheduling or planning of future dates, either — unless one friend asks you for specific advice, like what kind of food the other likes. If, on the other hand, your friends don’t click, don’t grill them about what they didn’t like. It’s awkward enough to say, “I don’t want to date your friend,” without having to explain that it’s because of his weird toenail habit.

Finally, if your setup doesn’t go as planned, don’t despair. It’s not always enough to bring together two people who look perfect together on paper. As Dr. Chasen explains, “you have to have a little luck, a little mazel.” And you can’t expect to get lucky every time.

Need help with a sticky social situation? Email us! We’ll sweep your social minefield!