How to Be the World's Worst Matchmaker

We've all had that inclination. Your friend is single. She's gorgeous. She's smart. She's killing it at work. Why is she single? So you mine your phone, and your boyfriend's phone, and his brother's phone, and try and figure out who is worthy of taking your friend out to dinner. 

It's a nice thought, but you're on a dangerous road. Allow me to be your tour guide of all the ways you can screw this up...

Step 1: Assuming They Want to Be Set Up

Did your friend actually ask you to set her up with someone? No. Not everyone who is single wants to meet who you think they should date. Either they like being single and are doing just fine on their own thankyouverymuch or they may not trust your opinion. In any case, if you haven't specifically been asked to play matchmaker, don't do it.

Step 2: Not Being a Matching Algorithm

Just because your friends are both hot and single doesn't mean they will enjoy each other's company. Maybe make sure that, for example, both people want to be in a relationship in the first place? 

A married couple I know, Matt and Colleen, set up two of their friends, Justin and Tillie. Justin was into Tillie, but only wanted to hook up with her. Tillie was looking for more. Not too far down the road it ended poorly (how poorly? Cops were called. No joke). Now they still see each other regularly at Matt and Colleen's parties. 

Step 3: Arranging an Awkward "Run-In"

One friend, we'll call him Rodney, left brunch with his female friend Allison. "Walk me to coffee?" she asked. He was going in the opposite way. "Just walk with me?" Being a gentleman, he obliged. Ten blocks later he had learned all about what an amazing woman Allison's friend was. Who was there when they arrived at coffee? Why, the very same friend! Rodney was able to play it off as a friendly introduction, but he never really trusted Allison again. If she wasn't straightforward with him about the set-up in the first place, what else would she be hiding about the people she's setting him up with?

Step 4: Over-Selling

Everyone thinks they have the hottest, coolest, most brilliant friends. That's why they're our friends, right? Yeah, well, some people may disagree with your assessment. Just because you think the world of someone doesn't mean the person you're setting them up with will too. It's better to offer a few facts and leave the rest up to the imagination. Let them discover how awesome the other person is. You're essentially selling a concept, not their resume.

Step 5: Doing a Double-Date

Don't be involved in their first date. Period. That means don't suggest where you think they would like to go. Don't "coincidentally" invite them out to the club at the same time and make them dance together. Don't hover and offer tidbits of info about each of them to the other. Just let them do their own thing.

Step 6: Not Thinking About the End-Game

A girl I know, Chelsea, was set up with a man by a friend. They dated for three months, he got serious commitment phobia, said he didn't know how to be in a relationship, and disappeared. The friend had withheld one crucial fact—the guy hadn't dated anyone in 11 years. Why would she omit such a fact? Because she hoped Chelsea would be "the one." You want your friends to be happy, but most set-ups do not end in happily-ever after. 

What can be gleaned from these stories? Only match-make when asked, and don't apply extra pressure. Cupid may have shot the arrow, after all, but he left it at that. 

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