Square Peg, Round Hole

He looked so good on paper. So many boxes. But one.

I have been pressing the rewind button in my life a bit these days to look back and learn from moments where I listened to my body and what happened after. I know the quote “don’t look back, you aren’t going that way” but I believe you have to look back to learn, remember and recover.

I scroll through the gigantic filing cabinet full of memories filed in my mind, I land on a folder in my mid-20s. I mentally pick up the folder and so many images fall out (all saved from Facebook galleries) when I had momentarily dated a boy who literally checked so many boxes for me in the romantic partner dream list. Did you have a list? I throw away all old journals but if I had some of them from the past, from this era, so many lists and dreams and more lists. So this boy, he made me laugh, super attractive and financially stable. He had an endearing relationship with his Mother, he was very athletic and so open to trying new things like: going to sit quietly side by side at the beach to meditate or joining a group Cross Fit competition with my work (only work out/wellness endeavors? I worked at lululemon in my 20s which actually feels like 100 years ago and I drank the kool-aid - that is another file folder). He had a quirkiness to him in larger social group settings but I actually enjoyed it as it gave me permission to be weird in my own way, too.

We were friend for years and people always would say things about us having crushes on one another or how we could have cute children - which is really odd to say, right?

So finally, I said let’s date.

He travelled and had a busy work schedule and I was immersed in my career, too so it was a very casual dating start. We were already friends so there wasn’t this huge get-to-know one another hurdle thing.

I acutely remember getting dressed up in this tank top that was the sweetest blue color and a black skirt and green ballet slipper shoes to go out to dinner. We were shifting from friends who met networking, hung out on and off and made out with one another (often times after a few drinks) to actual grown up dates without other people around.

All went well at dinner. Conversation flowed.

We went back to my apartment and I will tell you this, I could not take the relationship to the next level. Everything in my body and my mind collaborated with the most clear, “no, no, no” I had ever heard to date.

Square peg, round hole was the frequency.

A box (cough, my box) he could not check.