Why You Achieve Everything Except Your Wildest Dreams

Clear path. Lesser goal. Can’t lose.

John Gorman
10 min readJun 9, 2022


Photo by Aziz Acharki on Unsplash

I used to date. It was a fucking blast, and I was terrible at it. Literally, no one I’ve ever dated became a serious relationship, until the pandemic rendered dates impossible and I met my current partner — hey! two years together! — via being witty on the Internet and we got close by binge-watching sitcoms in our PJs. I’ve got to imagine, had we met the traditional way, that I’d still be single and probably living a meager, anonymous existence in the New Mexico desert.

Before every date, I would look in the mirror and tell myself: “You can do this; don’t fuck this up.” Then I’d get all gussied up to meet my next potential partner for drinks and/or food and proceed to … well, do exactly what I told myself not to do.

The dates were never bad, per se — minus one woman I met for Ramen who drove drunk to the date — but they ultimately ended in only one of three ways:

  1. We’d hook up.
  2. We’d agree to become friends.
  3. We’d never speak again.

We would never take our relationship to the “next level”. For a long time, I blamed myself: “You’re not good enough, Gorman!” “You’re an idiot!” Aw, man. If I had a dollar for every time I berated myself for a social or romantic faux pas, I’d retire immediately and … probably live a meager, anonymous existence in the New Mexico desert.

But I was good enough. (I think?) I’m charming as fuck when the stakes are low. And I could totally take a relationship to the next level. It’s just … you put me on a capital-D Date and all of the sudden I bust out the forced laughter, awkward silence, involuntary tics, boneheaded non-sequiturs, and sloppy bacchanalia. Ah, The Dark Art of Self-Sabotage. Let’s talk about that.

But First: A Video Lesson from A Dead Comedian

There’s a scene in the movie Tommy Boy — a slapstick comedy released in the halcyon days of the 1990s; back when the world was young and life was long and before my generation would come to understand profound disappointment — which my mind inevitably drifts back toward and becomes sadder with each successive revisit.



John Gorman

Yarn Spinner + Brand Builder + Renegade. Award-winning storyteller with several million served. For inquiries: johngormanwriter@gmail.com