Looking for Lifestyle Exclusives? Get your Cheeky Card!

Evaluating Relationship Happiness: From Shoes to Science

Official Boyfriend Investigator to the Rescue

by Sarah Gray – June 14, 2012

The first decade of the 21st century was the decade of “The Breakup” for me. This might have started sooner, but for some reason the ‘90s were a drought. A drought with only one oasis in sight: the memory of my ex – let’s call him Sammy – roaming around my broken heart.

But time passed. 1999 rolled over into 2000, the world didn’t end, and I settled into graduate school. It was thus that I embarked upon the course that would – unbeknownst to myself – lead me to become an Official Boyfriend Investigator.

That’s right, readers: S. Gray, O.B.I.

And how did I achieve this feat?

I studied!

By going through five relationships in ten years.  Notch, notch, notch, notch… not?

“OMG,”  you may think…. ”What was she doing!?”

Getting Fitted

I think, in retrospect, I was looking for the right fit. Someone with whom I felt happy, and someone with whom I felt like my best self. As we all know through growing up and trying on shoes, clothes, and personas, settling into that “just right” match – the comfy space between your fantasy and your reality – can take some doing.

But the cost of bad choices – being That Squabbling Couple; feeling bored; watching your frown lines come in – can be high. That’s why, having come out the other side, I am offering my services to you. Because who couldn’t use a little boyfriend investigating?

And who doesn’t like talking about shoes?

Let’s examine a few of the men I met on my well-heeled path to success. Just how well did they fit me?


Dating Mr. X. was like wearing a gorgeous pair of high heels: one moment I felt amazing, sexy, in charge; the next, my toes were burning and all I could think was “this hurts it hurts it hurts!” But every time I’d take off the shoes and curl up with a blanket, I’d see one poking out of my closet… and yearn to put it on again.

This glamorous drama lasted until I finally walked away for good – toenail polish, severe calluses and all.


Next up, Mr. Y. If Mr. Y were shoes, he’d have been a good, classic pair. I felt comfortable and well supported. But, like a broken version of Dorothy’s red slippers, they kept pointing me back to Kansas – even when I wanted to explore the big, vast world. We rarely went out, we fought over which house pet was more loved (the cat beat the fish, paws down), and I began to suspect he had voted for Bush.

Almost home – but not my home.

Bare Feet

“Forget picking shoes! I’ll wear whatever I want,” I muttered, going out with Mr. Z. The problem here was that whatever shoes I wore I’d learn everything – and more – about them.  The incline of the heel. The physics of the pitch of my butt as measured by the distance between my toe and the ball of my foot. Squared. On a romantic night looking at the moon, I learned about the rotation of the planets. I was drilled. I was schooled.

I was tired.

Satin Slipper?

And then… there was Sammy. He was the Cinderella shoes I had worn in my dreams – and he had returned, unexpected, a decade later. He was the slipper I remembered, that made me light, that danced me home. But I soon realized that the “home” we were walking towards was based on memories, not on our lives right now.

During one of my many attempts to shove my (very real) foot into my (very dreamy) slipper, I fell into despair.

The shoe didn't fit!

During one of my many attempts to shove my (very real) foot into my (very dreamy) slipper, I fell into despair.

I wasn’t sure how I felt, and I didn’t know what to do.

What I wished for, above all, was a big ‘ol scientific graph that would sit in front of me and inform me – objectively, of course – whether dear old Sammy was making me happy or not.  I felt there was too much at stake for me to decide “on my own.”

I needed tools.

I needed facts.

I needed…


So, web programmer by trade and passion, I wrote a computer program to help me out. Every day, I chose a smiley face or a sad face (out of five possible faces) to describe how I felt about Sammy. I didn’t peek, either: I wanted to write without being influenced by what I had written five minutes ago.

And I programmed my data to appear on a graph.

When my “reveal day” arrived,  I held my breath and looked. There, in front of me, were my words and feelings, telling a very clear story:

Computer. Says. Not. Happy.

Look at all the ups and downs!

On "reveal day," I could see this was not the picture of a happy relationship.

I won’t say the relationship ended right away. (It dragged on for many days months.)

Or that I was the brave soul who ended it. (I was a terrible coward.)

Or that the breakup was easy. (I cried for weeks.)

But it was the right thing to do, and I did recover.

Over time, I was able to emerge from fantasies of boyfriends past and tune into my own voice, my own needs, and my own present moment.

And thus, my field training as a Boyfriend Investigator was complete.

Unlike fire breathing, you can try this at home!

What I leave you with from my work is a little iPhone app that I wrote, so you can do some boyfriend investigating – and self-reflection – of your own.

Because getting out of the wrong relationship is the first step to finding the right one, whether it’s with him, someone else, or just by yourself for a while.

Sometimes things can be really good!

When you find the right relationship, you'll know it!

Cheeky Reader: if your boyfriend were shoes…

What kind would he be?

And how well does he fit you?

About the Author: Sarah Gray

Sarah Gray, Boyfriend Investigator, is a Cheeky geek who lives in Chicago's Rogers Park neighborhood. She builds websites and apps and helps people figure out if they should stay with their boyfriends.