I Paid A Matchmaker $4K To Send Me On 4 Dates, Only To Learn What I Was Doing Wrong

When I was just out of college, I made a list of 17 characteristics my future boyfriend would need to possess to be worthy of my love. 

My list was written in blue felt tip pen on the back of an envelope I took from the desk at my temp job as a receptionist, a job I would later quit when my boss wouldn’t let me leave early to meet my friends at a bar on New Year’s Eve. Yet the concept that maybe I had some work to do on myself never entered my mind.

Some requirements from My Perfect Man list:

• Taller than me (see: movies)  

• Wears Levi’s (duh)

• Likes and rides horses (let’s share passions)

• Reads poetry (sensitive types only)

• Writespoetry (may as well require some talent) 

Not long after the creation of said list, I met Jonathan Marks in an accounting class at the University of Chicago. There he was: tall, gorgeous, Levi’s-wearing, horse-riding, Princeton-educated, poetry-reading, poetry-writing Jonathan Marks. The man from the back of the envelope was real,and the dream-come-true of him warranted always using both his first and last names. 

For a solid two months, I thought we were dating. He called me; he picked me up on his motorcycle and took me to see “A Streetcar Named Desire.” Jonathan Marks told me about his family, showed me photo albums from his childhood and introduced me to his brother. 

But aside from the occasional brushing of hands and lingering hugs goodbye, there wasn’t anything physical between us. I thought he liked me so much that he didn’t want to risk doing anything too soon. But then Jonathan Marks hooked up with my friend Lisa. And after that, he started dating another pal named Kelly. 

My list of requirements for my perfect mate did not include:  

• Has sex with my friends.

I’m sure I kept some of my boyfriend requirements in my head as I stumbled through the singledom of my remaining 20s and 30s. Those years were jam-packed with many wine-fueled first date debriefs and relationship dissections ― he bought me a toothbrush, that means this is serious, right? ― but ultimately lacked any real romantic achievement.

By the time I hired a matchmaker in San Francisco at age 43, I knew enough not to trust my own instincts when it came to finding love. I had learned that some people had expertise in certain areas, and if you wanted to fix something you didn’t know how to fix yourself, you had to find a professional. 

Need to get fit? Hire a trainer. Need to get your head right? Go to a therapist. 

So I did my research and found Rachel, a consultant who worked at an exclusive matchmaking service that promised to help clients meet people they actually wanted to meet. It sounded a little too good to be true, but the testimonials and the photos of happily married couples helped me get over the $4,000 price tag. A shocking cost, but I was making big tech money and thought I was ready for a relationship.

Rachel was adorable. I liked her, even though I had questions about her compensation. She was making $4,000 for setting up four dates with no guarantee of anything more. But she assured me that the cost was going to be worth it for the time she spent really getting to know me and what I was looking for, not to mention the professional photo shoot sure to make me look desirable to her roster of potential men.

What stands out most when I look back at my meeting with Rachel was her reaction when we talked about what I was hoping to find in a partner. 

So, I feel like I have a good sense of who you are, but why don’t you tell me a little about the man you think might be a good match for you? Rachel asked. 

I tried to be specific without mentioning the horses or poetry even though, two decades later, I was still fantasizing about finding a man with those attributes. Instead, I told her what mattered most. 

He needs to be super bright. And successful. Somebody who has made it professionally. Somebody who owns a home, and a ski house wouldn’t hurt. 

Rachel smiled and nodded, encouraging me to continue while I wondered if she had a boyfriend.  

OK, so yes, he needs to be successful, but he can’t only think about work. I mean, I’d like him to have hobbies and enjoy sports or activities other than making money. And some interest in the arts – movies, books, a little culture. Oh, and it would be nice if he came from a good family that he’s still close with and sees on a regular basis.

Rachel looked at me and waited an intentionally long time before speaking. 

Sarah, do you know who you just described? 

I sat there staring at her in silence. 

After an uncomfortably long time, she cleared her throat.

You just described yourself, Sarah.

I heard what she said but didn’t quite get it. Her observation didn’t sink in, and wouldn’t sink in until years later.

I hadn’t yet learned that trying to date someone exactly like yourself or finding love from a specific set of criteria probably wasn’t a good idea — and that the checklists and matchmakers and thinking I could problem-solve my way into love were never going to work. 

The four dates I went on were awkward and awful. When you’re paying thousands of dollars, rather than just thinking, “Well, that doesn’t feel like a match,”you (and the matchmaker) want reasons. But there just wasn’t any attraction between me and any of the four men Rachel had selected for me. The whole thing made me feel worse about myself than being single. 

I paid a shit ton of money to learn that you can’t force attraction through a set of criteria. And, looking back, I can see why I made my lists: I wanted what I thought love was going to do for me. I was trying to fix myself by outsourcing what I needed to do on my own to somebody else — not the matchmaker, but the man.  

From the time I was a little girl and got my first gold star on a handwriting assignment, I believed self-worth was something you had to earn. That little girl turned into a gold star-chasing woman who looked like she had it all but was filled to the brim with secret self-loathing. 

I spent my entire adult life hoping that the right person, some carefully selected other, would make me feel better about myself. Guess what? Doesn’t work that way. I couldn’t comprehend that I had to find a way to feel good about myself on my own ― for being rather than doing. I was downright exhausted by the time I reached 40. 

The only thing that helped me fix what really needed fixing was therapy. I wanted to be out of pain, and for me, the solution was doing the emotional hard work to understand why I felt so bad about myself in the first place.

My therapist David was patient, didn’t push too hard when I got stuck, and let me come to realizations on my own so I could begin to understand the patterns I’d created. Only with that understanding did the slow, subtle shift into believing that I was really, truly worthy of love start to occur.

Therapy may not be the thing that works for everyone, but it helped me in profound ways I’m still trying to process. Here’s the big life lesson that took me so many years and so many dollars to learn: Until you fix how you feel about yourself, you’re not ready for a real, loving relationship. Only after I fixed my relationship with myself was I finally ready for the kind of big, capital-“L” LOVE I’d hoped for all those years.

Today, my requirement for a man is one single bullet, in the form of a question:

• Do I feel like the best version of myself when I’m with him?

And my answer continues to be yes, seven years after I started dating a man who showed up in my life when I least expected him, and only after I realized the most important thing on the dating list is ME.

Even as I continue the work of therapy, I can tell you that this love is better and more complicated and more fulfilling than anything I imagined. And yes, my imperfect man is right here, sitting next to imperfect me, acting as if my typing isn’t annoying. He doesn’t write poetry, but he looks amazing in Levi’s.

Sarah Gormley’s debut memoir “The Order of Things” is the story of finding love after 40 and how her return to Ohio changed her life in ways she never imagined possible. She owns Sarah Gormley Gallery in Columbus, Ohio, which operates from the belief that original art can be a source of joy for everyone.

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