I’ve always held the theory that you should wear your second-best outfit for a first date. You save your best stuff for a second date so you can pretend your wardrobe overfloweth. I’m sure you see the logic.
But I don’t usually follow through on my theories, so that day I was wearing my coolest jacket.
My housemates were waiting for me to leave; they were their typical supportive selves.
“Sick jacket.”
“Nice fit, dog.”
“You know your boy is feeling good.”
Reader—your boy was not. Stepping out of the house and into the bated early winter, your boy was feeling like throwing up.
But the date began well. Due in no small part, I assume, to the coolness of the jacket. Man, was it slick. A black bomber with baggy sleeves and silver ribbing. Comfortable pockets and a zipper on the tricep that—like my housemates—could not open up.
I’m sure you know how it feels. Your best stuff. Stepping into the confidence of clothing like it’s your skin. The feeling will recede, slip away, but for a few minutes you’re another man.
The date continued well.
“I was nervous for this,” she admitted.
“That’s funny. I wasn’t,” I said, confidently.
“Liar,” she said, correctly. “Get me another drink.”
So I got up, weaving through tall Dutch men and leaning against the bar with all the swagger of a twenty-one-year-old English major. A figure was slumped on the stool next to me. He looked more laundry than man. He looked like he might melt.
To my dismay, he met my eyes. Inspected me. Cracked his face open with a smile.
“Cool jacket.”
To which I mumbled thank you. I gave him a fist bump. He was beginning to say something else when I took my drinks and left him.
My date had not noticed, and we kept on, the laundry pile once and again dipping his chin in our direction, one blue eye peeking over his shoulder, shrouding us.
We continued telling stories we’d rehearsed to precision. I shared bad jokes and she ignored her developing regrets. I’m sure you know how it goes: trading quick glances, small touches, ignoring that something is gnawing in the back of your head. Something with teeth.
We’d met. I’d reached out my hand. Settled for a bump.
I was reminded of him weeks ago. I was in the airport, solo traveling. Seated away from me, a young dad was answering his son’s 800th question. I paused my music to listen to him. He was speaking with great patience, and even at 11 p.m., his weariness could not hide his simmering passion. Like his son, I, too, became invested in the difference between Sith and Dark Jedi. This was delightful.
When the dad passed by me later, I wanted to tell him that I thought he was cool. That his son would remember moments like this, or maybe not, but maybe sitting in an airport years later he would see other fathers with their sons and be struck with the kind of thumping, humdrum nostalgia that will knock you right over.
Of course, I didn’t tell him. Too scared. And look, the world was no worse for it. And what would one minute of my time have accomplished anyway? And no cause for concern, my graveyard of “almosts.”
Shake your head, God. I know. I was so close.
Ben Plantinga graduated in 2025 with an English major and philosophy minor. He moved to Chicago this September and is pursuing comedy while preparing for grad school. He enjoys basketball. He is no good at basketball.
