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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Rule #1: You will not be spilling secrets. What one person tells you in confidence, should stay in confidence. If there is a divulging of information—fears about the date, fears about the person, past hang-ups or relationships—you are not to tell. Listen, encourage, help where possible, but keep the other person's secrets to yourself. They're very capable adults. They'll find out on their own.


Rule #2: You don't care. Whether this works or not, it's cool with you. Let your friends know that you were happy to set them up, but beyond that, you don't care. What they do from here on out is entirely up to them. Would you love for your friends to hit it off and live happily ever after? Of course! Are you a realist? Yes. Acknowledge that it probably won't happen. Either way, you want to keep both your friends. So make sure they know you're not (too) emotionally invested in the outcome of this match. You just want their happiness.3 Ways To Add Happiness To Your Dating Life

Rule #3: You will not be the go-between. If things go great, you will not be feeling out the situation for one or the other and tipping them off with hints. If things go awry, at any point in a potential relationship, you will not be carrying messages for them. You are happy to sit across from them at dinner, taking bites of your salad and nodding as they talk about how the date went, but you will not be the go-between girl. You will never be taking sides. You are Team Neutral.

Rule #4: You will not be answering questions. It's going to be tempting for the matched twosome. You're sitting there. You're a wealth of knowledge about this person they barely know. They will probably ask questions. Your job is to zip your lips. Beyond the simple things—job, physical description, a few personality traits, very basic likes and dislikes—remind them that the information they seek will be saved for the scavenger hunt that is dating. You are not going to share too much. You have no intention of spoiling the mystery. 10 Questions To Ask Your Guy That'll Bring You CLOSER Than Ever

As for me? I've tried my best to lay the foundation. I'm excited to see how it goes, but I've adopted a realist mentality that this probably won't work. I am not expecting to become the next matchmaker extraordinaire and land my own reality show. This might be a one-time deal. Maybe I'll do it again, maybe not. But for this one occasion at least, I'm glad I indulged my instincts. I am crossing my fingers for my two friends, who totally deserve romantic happiness. 


Maybe they will live happily ever after. You never know, right? I believe in following the vibes and gut instincts you get in life. You never know what'll happen if you have that "feeling" two people will hit it off, if you have that "feeling" about anything worth acting on in life. Do You Follow Your Heart, But Ignore Your Instincts?

But for now, I'm staying blasé. You have to. You have to try and follow the basic rules of matchmaking. You have to let those crazy kids just go for it. Because no matter what happens between Brooke and Cooper, I still plan on having two great friendships with each of them.

*Names have been changed to protect the innocent, matched-up parties