I Moonlighted As A Small Town Matchmaker. Here's What I Learned.

I met the men separately and I met the women in one big group, I don’t remember why. This was probably something I saw on an episode of Millionaire Matchmaker and it appealed to me. It made me feel like I knew what I was doing. I wanted to be taken seriously in this. I was already an office manager at an optometrist’s office, and I wrote a weekly column for the local paper about being a single mom to four sons. The office manager job was good for Friday pizza lunches and the steady paycheck. But the newspaper job legitimized me and gave me a voice, e, a bit of local power, and a not-so-hefty $50 a week, which was paid to me whenever the newspaper felt like paying me.

Most importantly, the column gave me access to readers. Many of whom thought I held some sort of secret to help them find partners. Fellow single moms, retired cops, sailors, teachers, that one farmer at a cafe who caught me unawares. I’m not sure why, but I got dozens of messages from readers who wanted to find love. Who thought I, a woman who had been single for 10 years, was the key to their love life. After a year or so I decided I agreed. They had to be right. I must know the secret. And so I did a little reality show research and set a date for my first matchmaking dinner party when my kids were away. I had a new dip I had been wanting to try anyhow, so what was the harm? I charged $100 per person for my services, which I said would be a simple meet and greet for local singles.

I vetted the local singles at my favorite local cafe before handing out my home address. I set up individual meetings with the men to talk about what they wanted and who they were. It was a revelation; so many lovely men, shy men, awkward men who just lived quiet lives and weren’t sure how to meet women. Single dads, widowers, shift workers, new transplants who didn’t know where to start. These coffee meetings ignited something in me. An empathy I had been missing for men trying to find love. They also buffered me against the less lovely men. That one who pointed to my body when we met and said, “Not one that looks like you.” Another asked me to “get him” a woman who would fit on his lap when he got home from work at night. One misguided widower who told me his housework was falling apart since his wife died. He needed a new one fast to cook dinners and such. I told him he might want to consider hiring a cleaner. He invited me out for a pancake supper with hope in his eyes.

The women were different. Tired. Excited. Jaded. Frustrated. And, I’m sorry to tell you, generally focused on indefinable elements. Height was a big one. Lots of women talked about height in our meetings. A sense of humor was a must but also bad news for the serious local men I had invited for the first singles dinner. Buzz words were popular with a lot of the women I met, words like “spark,” “charm,” “chemistry,” and “quality.” They promised to keep open minds and I promised to introduce them to some single men and also give them sangria since they were paying me.

Over the course of a year, I hosted six dinners. I made enough money to pay for my kids’ Christmas and to cover all of those cupcakes I insisted on baking. I met dozens of local singles. I bought a pink couch from a single funeral director who reluctantly came to one dinner. I introduced my son’s English teacher to a photographer who seemed like a good fit. I was invited to go sailing with a single dad of three girls after he met a single mom of three boys, Brady Bunch-style. I was kicked off Plenty of Fish, the only dating app anyone seemed to be using at the time, presumably for poaching business. I started to really believe I was good at this even though my own dating life had ground to a complete halt. Even though I was getting disheartened and depressed over how many singles said the exact same thing over and over again.

My success stories were few — very few — and far between. I suspect that one couple I set up stayed together because I begged them not to break up and ruin my only success story. They have since moved on to other people, picked out without me.

In the end, none of my research on how to find love helped anyone at all. Not the little tricks I learned from reality television; none of the advice I doled out to the local singles that I found in books and made absolute sense on paper. None of it really changed anyone’s minds about anything. So I quit the matchmaking game for good.

The bright spots? Older ladies who came to meet men their age (and were subsequently completely ignored) became travel friends. I perfected my sangria recipe. And I learned a little something about relationships, primarily that no one knows what they’re doing.

But everyone loves to keep on trying.

Jen McGuire is a contributing writer for Romper and Scary Mommy. She lives in Canada with four boys and teaches life writing workshops where someone cries in every class. When she is not traveling as often as possible, she’s trying to organize pie parties and outdoor karaoke with her neighbors. She will sing Cher’s “If I Could Turn Back Time” at least once, but she’s open to requests.