Gena Kaufman, Glamour magazine
To me, "I know this great guy for you" is right up there with these 9 other worst things to say to a single person…
As a person who is frequently guilty of the also annoying "Where have all the good men gone?" lament, I probably should be grateful when someone tries to set me up, but I usually just want to crawl under my bed and hide. That said, it works for some people and can be a good way to meet guys with real potential, provided you follow some basic guidelines to minimize the awkwardness and avoid under-the-bed hiding.
Keep it among your inner circle. Don't offer to set up people you barely know. A friend g-chatted me today to say the girls in the deli she frequents for lunch offered to set her up with another guy who works in her office building (hence, inspiring this post). Um, other than perhaps a mutual love of turkey on wheat with a little mustard, what exactly do you know about these people that indicates they are a good match? You don't even know their last names!
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Beware of the consequences: As in the situation above, people who work in the same office have infinite potential for awkward run-ins if the date goes poorly (not to mention they are both totally going to avoid your deli, whoops! Bad business.) A similar concept applies for people who live in your apartment complex, people you might be seating at the same table for your wedding, etc.
Arrange a casual meet up, if possible. I'm a big fan of this move: if you can possibly get the two in the same room without mentioning a setup, then just do it and see what happens (and feel totally smug when they both pull you aside to ask if the other is single). This only works if there's actually a reason they should be in the same room, like your housewarming party. If it's going to be an elaborate, obvious ruse to get them to the same place at the same time, just ask if you can set up an introduction or blind date.
Ask them both before you go all full speed ahead. Run the idea of a setup by both parties before you get one party all excited about meeting his potential dream woman only to later have to tell him "Sorry dude, she said she's not into bartenders. Or your beard." Ouch.
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Base your matchmaking on something. Something other than "You're both single." Or heaven forbid, "You're both gay," the rudest, most stereotypical and unfortunately frequently used reason to set people up of all time. You can't predict if there will be sparks, but you should at least think they'd have enough in common (again, beyond their similar lunch orders) to spend an enjoyable evening together.
Follow up if you must, but tread lightly: You may be dying to know how it worked out on your little love project, but they may not feel like sharing all the dirty details. A simple "How did it go?" will suffice, and if they change the subject, don't press it. On the flip side, if you're the one who was set up, don't overshare to your matchmaker, particularly if you thought the date was a total disaster. Remember, you are insulting both their judgment and their friend/family member/deli customer if you say "OMG, that was the Worst. Date. EVER!"
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Don't force the issue. If you just know two people are right for each other, but they won't cooperate with your plan, let it go. This was never a set up situation, but my friends Emilie and Mike are clearly perfect for each other, and everyone in our group of friends knew it. The two of them, however, refused to make a move on each other for years. We let them figure it out (without too much pressure), and they are getting married this fall. But I think they'd both agree that forcing the issue before they were ready could have ended in disaster. Or you know, we could have just been wrong about them being a perfect match. (Luckily I am never wrong.)
There you have it. Go forth, matchmakers, and make me a match. No, but seriously...do you know someone who'd be a good match for me?
Have you ever been set up? Was it successful or not? Or, have you ever made a successful match among friends?