How To Set A Friend Up On A Date Without Looking Like A Jerk

Photographed by Ashley Armitage.
So you have these two friends and you just know they'd be perfect together. You can't stop picturing their first date, then their one-year anniversary, their wedding...and omg, they'd be the most adorable parents. Eventually, you find yourself channeling your inner Cher (of 90s rom-com fame) and plotting the perfect way to set them up. Who cares if neither of them asked you to meddle — they're both single and they deserve your help, right?
Maybe your friends would love for you to arrange a blind date, but if they've never asked you to set them up, it's best to approach the situation cautiously. Some people might read your enthusiasm as judgement, and assume you think they're lonely, desperate, or can't find a date on their own. But that's not super likely, says Julie Spira, a matchmaker and online dating coach. "Most singles complain that their friends aren’t setting them up," she says. "So when an offer comes in from a friend to introduce you to someone who’s single, it should be welcomed with open arms."
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That doesn't mean you can run off and tell your friends they're perfect for each other. First, consider why you think they're a good match. Do you desperately want to set these two people up based only on shallow characteristics, or is there real compatibility? If you're trying to make a match happen just because they're both gay or both Black, that can be offensive. The potential couple needs to have more in common than that. "Maybe they appear to be a good match because they’re geographically desirable, have similar political views, share the same religion, have a similar sexual orientation, and both love riding bicycles or running marathons," Spira says. "But the perfect match on paper doesn’t necessarily translate to having chemistry IRL." There's no real formula for knowing when people would hit it off, but Spira says the best matches happen when you know both people really well and suspect that their personalities would mesh. So if you're going to suggest a blind date, make sure you're doing it for the right reasons.
And you should approach the situation lightly. Spira suggests saying something like, "How would you like to meet a great guy [or woman or gender non-conforming person] who I know?” You're doing two things here: By making it a question, you're giving them space to say no if they're not interested in a set up and by labeling a potential blind date as a "great guy," you're telling your friend that you've already vetted this person. If your friend(s) value your romantic opinion, giving someone your seal of approval can mean a lot, Spira says.
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But if your opinion doesn't really mean that much to your friend, or if they just don't want to deal with dating and romance right now, don't be offended. No matter how convinced you are that your friend would fall head-over-heels for the person you want to set them up with, it's your friend's love life so they have every right to tell you to buzz off. No one likes being pushed into something they don't want to do, so that's your cue to pull back.
Even if they do agree to the date, you should still back off, Spira says. As a matchmaker, it's your job to introduce the idea of going on a date and to exchange contact information or introduce them in person. It's not your job to plan the date for them — unless you're also going to be there. "The easiest solution is to suggest a double date or group date to introduce someone new to your friend," Spira says. "This removes the pressure of having them be alone with someone they don’t end up having chemistry with, which can backfire and be dreadful." But if they'd rather get to know each other privately, then pass along contact info and let them take it from there.
If the date goes well, you'll probably hear about it immediately. If not, then your friends probably won't say anything until you ask. "They won’t want to hurt your feelings," Spira says. "It’s fine to ask how the date went, as long as you don’t appear to be meddling." If you're planning to continue matchmaking, knowing how the date went can help you learn more about your friend's type for next time. But be nice, and try not to look too disappointed that the couple you envisioned didn't work out.
And be nice if they end up loving each other, too, especially if one or both of them were reluctant to go on the date in the first place. "There’s no need to say, 'I told you so,' to someone who was hesitant," Spira says. "If the date goes well, they’ll likely be thanking you, along with their lucky stars, because dating and being in the trenches can be exhausting."
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