The Rules Of Playing Matchmaker For Your Friends


One writer plays Cupid to her two good friends, and talks about the boundaries she will not cross.

Matchmaking is an old practice. Before dating as we know it, there was matchmaking.

On the frontier, because farms were far apart and it was hard to meet other eligible singles, families used dances to set up their children. In medieval times, Catholic clergymen and Jewish rabbis played Cupid within their communities. For centuries, European royalty consistently matched up their heirs-to-the-throne with heirs from other countries for diplomatic alliances. I could throw out many more examples, and I'm sure you could too. This matchmaking business? It's not a new thing.

Except, for me, it was.

I've never attempted to play matchmaker in my life. I love to give advice. I love to hear about my friends' relationships. But to actually facilitate a set-up? Isn't that like tempting fate or something? Asking for disaster? Doesn't the finger point back at you if things go south? But then again, this was new. This had never happened before. This "feeling." /node/77007

When I met Brooke* about two years ago, I thought of Cooper*. I don't know why that happened. The thought just scrolled across my mind like a flashing sign: Gosh, I think those two would really get along. But that was that. It was just a thought. At least, on that day.

Brooke and I started having weekly lunches where we dished about guys and relationships—our hang-ups, likes, dislikes, fears, excitement and so on. And our respective sets of friends would sometimes come up, too. Cooper would occasionally enter the picture in a story from the past, because we'd been friends since high school. And once, Brooke asked to see a photo of him. In the days of smartphones, that becomes just oh-so easy. I loaded Facebook. /node/151468

"Aw," she said, a big smile crossing her face. "He's cute." She handed the phone back to me. "I like Cooper." She put her fork back to her plate, beginning to eat her Pesto Cavatappi again.

My mind started speaking to me. I could not shut it up. The same flashing sign started blinking: You know, Jenna, I think those two would REALLY hit it off... They were each other's types. They had that same love of indie music. They had a similar sense of humor. They were both secret romantics, and very smart, with huge hearts. They were both people I loved and respected.

"You think so?" I asked. "Aw. Good to know!" I said nothing else that day. But I started to feel out the interest of both parties.

Cooper seemed open when I brought up the subject. After a slight nudge on my end, Brooke seemed to like the idea. It took months to get the seed planted, get them both in the right place in their dating lives, get them exchanging texts, and eventually get a date set. But they are finally going out. Officially. Tomorrow. 5 Dating Tips From The Millionaire Matchmaker

And while I'm excited to see how it goes, I did lay some ground rules for this whole scenario. Rules I plan to stick to, because no matter what happens with a potential match, at the end of the day, I want to keep my friendships intact. If you ever plan on setting up your friends, here are the rules of engagement. Read on...

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