How To Set Up Your Single Friends — & Not Make It Awkward

If all your friends are single, and tend to gripe about how hard is to meet someone, it can be very tempting to want to put on your Yenta cap and get involved. Personally, I have a mental rolodex of my single friends' "types," in hopes that eventually I'll be able to match them with other single people I know. Being the middleman in this sort of scenario can be intrinsically rewarding, because you get to claim some bit of responsibility for your friends' happiness. But on the other hand, it can get awkward very fast.

Recently, a friend told me that they were interested in another one of my friends, who happened to be single and looking. I gave my unsolicited blessing, and they went on a date. I learned the next morning that the date went well. Typically, I'm so nosy I can't help myself, but in this case I didn't really want to know all the dirty details. They're both my good friends, and it was their business.

As things progressed, I was put in a pickle: I had one friend sharing detailed feelings about the relationship, while the other was being vague and stingy with the intel. If the over-sharing friend wanted the receipts from the tight-lipped one, I felt I owed them to her — but asking for them also felt like crossing the quiet partner's pretty clear boundaries. In truth, I wanted to meddle, but I wanted them to be happy (maybe even together) even more.

It eventually did not work out for that couple, and in the end I felt weirdly guilty that I had failed them both. Should I have meddled more? Kept my hands off? Is this all my fault?! Not necessarily, according to Meredith Golden, a matchmaker and dating coach who specialises in online dating. According to Golden, it's very normal to feel responsible when a setup doesn't go according to plan.

So what's the right way to set up your friends? The most important thing is to be transparent, Golden says. "Be clear with each single person about your objective, and make sure each wants to be set up," she says. To that point, it's not worth it to play coy about the whole thing. Tell your friends what's up — and see if they're game — rather than surreptitiously putting them in a room together and hoping they pick up on the hints. "It's a disappointment when [you're] trying to orchestrate a setup, and one of the participants doesn't follow through," Golden says. My friends were both interested in meeting one another, so we were off to a good start, at least.

Step two might've been where I went astray. Once the connection happens, Golden says, you have to back off. "Your role is to set up, not meddle," she says. If you're really curious, you should follow up with the person you're closer to, or whomever is your priority, she says. This is tricky when you feel equal allegiance to both friends, but talking to both about the other could actually make things worse. "You did your good deed, now let it go," Golden says.

Golden is very strict about the no-interference rule, because it usually backfires — for the matchmaker. "The messenger always gets shot, and who needs this?" she says. For example, if someone confides in you that the date went terribly, it's not your place to deliver that info to the other party, who may end up being hurt (by you) in the process. But if the complaint could be turned into a helpful reminder (say, your friend didn't confirm the plans until the last minute), Golden says you could let the offending dater know where they've got room for improvement. "Even if it is helpful, be very careful in the delivery," she warns.

In my situation, I found myself justifying one friend's poor behaviour just to make the other friend feel better about the fact that it wasn't working out. If it were a stranger dating my friend, as opposed to someone I know and trust, I wouldn't have been so invested in seeing the relationship through — and that's a good sign that I needed to disentangle myself. I likely couldn't fix whatever was broken between them, anyway. The good news is, even though it didn't totally go as planned, we're all still friends.

Perhaps the best advice for anyone trying to set up their friends is to not take it personally if it's not a love connection — or if the singles involved would rather not give it a try. If a pair you set up eventually calls it quits, that isn't your fault just because you were close to the situation at the start (especially if you've followed the rules and backed off after the initial intro). But Golden optimistically reminds us that when setups go right, they are amazing — so it's worth a shot. "If you have two friends who you think might hit it off, definitely introduce them," she says. "It's a win to facilitate something positive, especially if you believe in Karma."

In other words, don't let the fear of striking out keep you from suggesting a game — just remember you're not on either team, and you're definitely not the umpire.