How to Be a Great Matchmaker

I've talked a lot about why matchmaking is fun (opens in new tab). Today, I want to talk about how to be a good matchmaker. Of course, it's really quite easy — as long as you keep a few things in mind.

1. Show your hand early when you meet a good candidate. When you come across a super-cool single guy at a party or work event — but you can tell immediately you'll never have a love affair with him — express your intention to set him up. Say something like, "You're so great that I've got to get your card — or else you have to tell me how to find you on Facebook — because I know there's someone I should set you up with, even if I can't figure out who it is yet."

2. Find out what your friends and acquaintances are looking for. That makes it easier to sift through all the members of your vast social network and put together a solid potential hookup. For instance, I tried to set up a female friend of mine from college with a handsome man of Indian descent whom I know from my neighborhood. After I described him, she said, "He sounds great! But he's not Jewish, is he?" In that way, I found out she was only interested in Jewish dudes — so a few weeks later, she immediately came to mind when I met a friend of Easy Walnut (opens in new tab)'s who really wanted to find a Jewish chick. Similarly, I have a friend who was raised strictly Muslim who is now agnostic — so whenever I come across a woman who has also chosen to step away from the strictly religious lifestyle she was raised with, I think of him.

3. Explain thoroughly. I always try to let people know exactly what they're in for, so nobody walks into an evening only to feel like I've sold him or her a bill of goods. So I will say things like, "He's a little short for me — but since you're three inches shorter than I am, I think you guys would look great together." Or something like, "He's into God, and I'm not — but maybe that won't bother you as much as it bothers me." Or, "Honestly, he's not devastatingly handsome — but he is so hilarious and so sweet and so successful that I think you really should meet him."

4. Take risks. I think it's far better to err on the side of noncaution — as long as you follow Rule #3 — because you'd be surprised to find out how many really cool people have a hard time meeting other cool people.

5. Do your best to make sure you have pictures before you try to set them up. Because in this day and age, people want pics. And they're easy enough to download from Facebook. Of course, you can always just tell people to Google each other.

6. Explain that you will bow out for a while after they meet. Otherwise, you might become the consigliere for both people, which can be an awkward position — and could lead to one or both of them feeling annoyed with you. What's more, your days could be consumed entirely by advice-giving and e-mail interpreting if you're not careful. To make sure matchmaking doesn't turn into a full-time job, make it clear you plan to withdraw from involvement until the relationship either becomes solid or else is clearly going nowhere.