I Only Suck When I Try Not To

Or, this is why I’m still single.


I went on a date last year — well, I went on a lot of dates last year, but I want to talk about one in particular — with a woman I really, really grew to like. We’d met at an event in March, just after my last long-term relationship ended, and through a series of increasingly flirty texts and meetups it became fairly clear that we’d grown to really enjoy each the idea of other. In July, I asked her out for drinks at a cozy little speakeasy my friend tended bar at. She said yes. My pep talk to myself consisted of seven words: “You’ve got this. Don’t fuck this up.”

I’m a local musician, and was slated to play a set at a next-door bar in the two hours before the rendezvous, but I was called off at the last minute and found myself meandering about Downtown Austin two hours ahead of schedule and with nothing to do. So I went to another bar where I was friendly with the staff, joined them for a few shots, chopped it up with them and generally tried to put myself in the optimal mood to have a charming evening out. I was tipsy when I finally met her.

The date started fine, with conversation evolving breathlessly and effortlessly, smiles and laughter flowing freely, attraction seeming to peak as the night wore on. She copped to liking me since we first met, and I did the same. We kissed. And, some 150 minutes in, we were both forced to confront the two-ton elephant in the room: I had started with a seven-drink head-start. I got sloppy. I got messy. I got weird. The bartender cut me off. She left abruptly, and that was that. When I woke up the next morning, I was in my bed with my oxford and slacks still on, and I opened the Uber app to rate a ride I couldn’t recall, from a driver with an unfamiliar face. There was no second date, and I was forced to reconcile the harsh reality that I had done the one thing I told myself not to do. I fucked it up. I did not get a do-over. I quit drinking a month later and haven’t drank on a date since.


There’s a scene in the movie Tommy Boy — a slapstick comedy released in the halcyon days of the 90s, before I understood true disappointment — which my mind inevitably drifts back toward and, with each successive revisit, makes me more profoundly sad.

In it, the titular character (played by the profoundly talented, hilarious and gone-from-Earth-too-soon Chris Farley), down on his luck and nearing the end of his rope, accosts a waitress with a deep dive into his failings as a salesperson.

He waxes — with his trademark cartoonish bombast — about how, with the stakes high as hell and when presented with the opportunity to get what he wants (in his case: a closed deal), he gets himself all worked up and excited, and, despite his best intentions and efforts, inevitably finds a way to screw it up and walk away empty-handed, confidence shot and wallowing in his own misery. I feel you, buddy, I feel you.


I don’t suppose I need to tell you I’m not in sales, and can’t fathom an alternate universe where I’d be a cold-blooded shark with money on the line. I’m clearly not wired that way. But this pattern of behavior — of finding what I want, going after it a little too hard, and killing all hope of ever achieving it — manifests itself in a myriad of other arenas. I’m a dreadful mess in job interviews and pitch presentations. I avoid tough conversations and procrastinate important, emotionally draining tasks. As a child, I spent five years striking out as a baseball player, despite routinely hitting the ball well in practice. I routinely forget the words to my own songs when playing on stage. I tend to choke in situations when hard-earned success is near: nearing victory in a friendly game of darts or pong, flaking and flubbing when offered the opportunity to earn money for my own writing. Reaching my ideal weight over a disciplined six months and eating myself out of it on a six-week bender. Melting down on Twitter after having finally achieved the zenith of my career, and knocking myself back to Square One. The list goes on.

Nowhere does this fundamental flaw present itself more glaringly than in the domain of love. I‘m relentlessly awkward around women I’m attracted to, and I rarely ask them out on dates. When I do, they often say no. If they don’t and say yes, I’m often stilted and boring. I tend to be overeager, overtly flirtatious, and an overbearing over-sharer, in text or phone discourse with a potential partner. I rush things — I burn too hot then explode in a supernova. These cycles repeat themselves, and I spend a majority of my days wondering why I get this so wrong, despite knowing better.

More puzzling still, none of this applies when faced with situations when I’m smitten with women for which I’m unburdened by the potential for long-term love. There was fling with the 22 year-old model who moonlights as a singer and poet. The on-again, off-again puppy love with the 43 year-old Senior VP at a large global tech corporation. The cross-country tryst with an endlessly fascinating actress and world traveler. The white-hot three-month romance with a woman who’d only been with women before. The multiple women who step out of their marriages for fun and games with me. The pageant-queen daughter of an NFL football coach who was only in town for the night. Too young. Too old. Too far away. Too committed. Too temporary. All but two of my girlfriends have been long-distance. Half of them were dating other men when they fell for me. I became miserable in secure relationships, and insecure in relationships I adored. All of them ended, except for the ones that never were. Once the simmer becomes a boil, the water evaporates, escaping away from me never to return. Apparently, the lower the expectations, the easier I exceed them. Which leads me to ask myself, ad nauseum, why? Why do I fly so confidently on ground then crash when I try to take off? What is this glitch in the mental matrix?


Of course, I am describing the dark art of self-sabotage. A coping mechanism that simultaneously laser-focuses my mind on exactly what I want, and then either actively ensuring it never happens or helplessly letting the opportunity pass me by. It’s built on a bedrock of fear — not a fear of success as commonly believed, but a fear of either failure (rejection), or of the loss of identity that comes along with success (impostor syndrome). By engaging in self-sabotaging behaviors, I am actively hedging, and excessively mitigating risk. The loves I’ve had in my life — those effortlessly conjured out from under the weight of high expectations — have been generally low-risk. The loves I’ve left behind or failed to pursue in the first place are examples of me failing on my own terms, so as not to lose my identity. But … what is my identity? And why is self-sabotage baked into it?

Although I am confident in low-stakes situations, my self-sabotage stems from a poor self image rooted in early life experiences I internalized as indicative of my intrinsic character. I was often called “weird” and “ugly” as an awkward middle-schooler around the time I started becoming romantically interested in the opposite sex. I was rejected a lot. I internalized this as a general sense of unattractiveness and unworthiness. But why couldn’t I work through that? After all: the mark of a high character, confident person is the ability to shake off the haters.

Even earlier than that, I’d developed an abusive inner monologue — a voice that’s constantly engaging in negative self-talk, slinging some of the most profane, profound insults you could ever hear — saying things you’d never utter to even your worst enemies. I grew up in an environment where failures were chastised as character deficits, or signs I was pursuing the wrong things, and not as stepping stones or opportunities for growth. And the fear of failure, and a resentment of success, were (in some cases) literally beaten into me for as long as I could remember. Failure, and avoidance of it, became the central focus of my mind. I became pathologically scared of rejection and other people’s perceptions of me. Which is why — as explored earlier — I say yes to everyone who wants me: the people I am comfortable around but not really chasing. It is also why I become too self-conscious, stilted and awkward in situations where love is on the line. I wait to pursue love until I feel sufficiently comfortable in my own skin and confident in my own attractiveness and worthiness. I don’t need to tell you that moment never really arrives. Yes, it’s a form of procrastination, and it’s also a form of perfectionism. But how would I know when I’ve become attractive and worthy of love? What does attractiveness and worthiness feel like?


It’s time to talk about Impostor Syndrome. Fundamentally, it’s a feeling of fraudulence, like you’ve crashed a velvet rope party you clearly don’t belong at. It’s that fish-out-of-water feeling you get when you’re more successful than you’ve ever expected to be. Why does this happen?

It’s probably a cliche metaphor at this point, but imagine your level of success and happiness and love is controlled by a master thermostat in your mind. We all have a set range with a lower and upper limit. Impostor Syndrome is triggered when you hit the upper limit of your life satisfaction thermostat and failure becomes too hot to handle. It’s why I diffuse praise heaped upon me, and dwell upon criticism. It’s why I become avoidant of people I deem as too needy or affectionate, then become desperate when I’m lacking affection or not feeling needed enough. I’ll give you an example: In 2012, I was homeless and jobless and flailing in life. I was miserable and felt like a failure and my abusive self-talk eventually drove me to turn into a workaholic where I’d out-hustle my demons. By 2016, I’d increased by income by 10x, lost 50 pounds, found myself in a happy, healthy relationship, and was blessed enough to achieve so many goals and experience areas of life beyond my wildest dreams.I had triggered my upper limit. Failure became too hot to handle. The alarm of Impostor Syndrome began to ring. I began to worry. I looked down from the impossibly high ledge I found myself perched upon. And I began to view that success as unsustainable. What happened next?

I began indulging on slothful, lethargic, mindless comforts: drinking to excess, watching hours of Netflix, habitually scrolling through social media, eating full large pizzas in one sitting. Things I was used to and fit more in line with my self-image and self-talk. And those habits and indulgences gave me built-in scapegoats and excuses for not finding love. To return to my original story of the date I went on last year, I could now confidently explain away the failure to launch as “it didn’t work because I was drunk,” instead of “it didn’t work because I wasn’t good enough for her.” By being anything other than my authentic self, it dulled the sting of perceived inevitable rejection. Or, even if the relationship worked out, I never had to feel like a fraud who had outkicked his coverage or enjoyed the company of a partner I didn’t feel I’d deserved. Yes, this is all in my head. Yes, I’ve internalized the wrong thoughts. How could I possibly fix it?


It started with challenging my thoughts, my behaviors and my coping mechanisms that have been elemental in my evolution (or lack thereof) as a human — externalizing my abusive inner monologue as someone else’s voice and fundamentally, truly asking myself who I am, what I am capable of, and what I am worthy of. I’d be lying if I said this work was easy, or even complete. I spent the vast majority of the previous year crisscrossing the country attempting to overwrite my memories of who I am with newer, healthier, happier ones. I pillaged my past and leaned into failure. It was emotionally draining, harrowing and not without missteps, backslides and upheaval. The anxiety that recreating an image of yourself from the ground up is excruciating and difficult. I went to therapy. I said goodbye to toxic people. I started actually asking women I liked out on dates. (I got rejected a lot, but I was getting used to embracing the word “no.”) I’m not all the way there … I’m not even close. But the foundation is starting to form. Only incremental change will be lasting, for — as I mentioned earlier — becoming a workaholic and 10x’ing everything is a surefire sign that I’m flying too close to the sun.

Will I ever succeed? How will I know when I do? It will take shape when I learn to trust myself that I’m along the right path. When I am able to step out of my own head, silence my inner critic, and — most importantly — lose my sense of self. For self-consciousness is enemy of existing in the moment, with conversation flowing freely and the seeds of love able to find fertile soil to take root.

That’s how I’ll beat back my backslides into sex, booze and comfort foods. That’s how I’ll know I belong at the party. That’s how I’ll grow to embrace risk and rejection. That’s how I’ll have the courage to say yes and the discipline to say no. That’s how I’ll avoid my Tommy Boy moment. Only then, absent of the self and the self-destruction caged within will I then be free to go after what I want, make peace with my worthiness of them, and be free to explore the good and healthy and loving parts of this life I am so lucky to have. And there’s nothing that’s more sexy than that.

Personal Growth

Sharing our ideas and experiences.

John Gorman

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Inspiring essays about life, love, sports and music. More words + pics at: https://www.instagram.com/heygorman/

Personal Growth

Sharing our ideas and experiences.