A local music fan in attendance at the Thompson Wedding, October 2016.

Hello, this is my 30-day song challenge done at the same time.

DAY 1: SONG YOU LIKE WITH A COLOR IN THE TITLE

“Ivy & Gold” — Bombay Bicycle Club

I discovered this via someone I briefly chatted up on a dating app, discussing her playlist prowess, particularly one for a weekend getaway in Joshua Tree. I thought it was funny how someone can pop into your life, give you something neat, and then readily disappear.

DAY 2: SONG YOU LIKE WITH A NUMBER IN THE TITLE

“Thirteen” — ¡Forward, Russia!

I caught this radio debut on a drive home from college and it remains the only time I felt like I was the only person who knew about a band and…


This is Christopher Heard, man about town before the sun goes down. Photo by Ellen Callaghan.

a delectable offering of the nightlife surrounding the thoughtful performer Chris, if it were hastily written by Tennessee Williams.
by Jake Kilroy

SCENE ONE

The parlor in which we find our lost souls is a new place that pretends to be an old place so that trendsetters who live on and trip over the cutting edge can pretend they are not so concerned about the future, but rather appreciators of the journey that got them to where they now find themselves, battle saints in the wilderness of hip, a sprawling landscape that makes up the lonely frontier of cool. …


Photo: Alice Yoon • Dubrovnik, Croatia

The season before my first broken heart, I often found myself on the castle walls, welcoming the sea breeze as heartily as I had the carmine berries my village eventually decimated. We love what we have until we can no longer. Or we ignore love until it is upon us, seen each year when the healers would tend to the wounds of the warriors and suddenly match eyes anew.

Atop the walls, I thought of her, each time coming to rest where the western wall met the southern wall, the old man would nap, and the gulls would fill the…


Getting Money for My Poetry

It is without exaggeration that I say one of the coolest things I’ve ever done is be commissioned to write poetry. This has happened exactly one time and it was only recently — curiously enough for Red Bull.

I was brought onboard by extremely good design agency Hoodzpah, charged with art directing Lindsey Vonn-specific zine as a ridiculously dope retirement gift for the legendary skier, ultimately to be published in Red Bull’s June issue of The Red Bulletin. In need of a writer, they hit me up with my poem “The Heavy King” as reference material.

Writing with a commissioned…


Please enjoy these selections of fake laughter from the Vanity Fair profile piece “Jake Kilroy Is Happy to Be Here.” Photographer: Scott Barman (May, 2019)

I’ve never been set to have a year like this and I can’t wait.

Today’s my birthday and life is good.

I’ve never been this productive. I’ve never been this involved. I’ve never been this proactive. I’ve never been this grounded. I’ve never been this mindful. I’ve never been this earnest. I’ve never been this open. I’ve never been this healthy. I’ve literally never worked on my upper body until now.

A Recap of the Good, the Bad, and the Ugly

I’ve had a tremendously fun existence: Once: 100 Moments of a Dunce’s Life.

It eventually got weird and I realized I could do better, so I changed things up…


Tony with his ’63 Impala, May 2019.

Anything is as much everything as it is nothing. How do you fill something without parameters?

I’ve wondered this since I first pitched The Perfect Person Project, my decidedly indefinite standing offer to learn anything from anyone. Asking the public to teach me whatever is a task so preposterously open-ended, it felt like I could lose my way after the first few steps.

But yesterday I scored my first education and it turned out to make total sense — and that is largely in part to my first instructor, Tony.


Check out how much better Blake looks in this photo than me. This is a perfect example of where I could learn from friends. Photographer: Rex Bang (April 2016)

Nobody’s perfect. But you can be better than you were.

To recap, I was existentially damaged/drifting/trampolining in a low-ceiling celestial chamber and now I’m as wide-eyed as I used to be on uppers with a healthy brain that would’ve suggested identity theft as recently as last year. [For further reference, you can read about my journey’s inauguration in I’m Trying to Not Be an Out of Control Mess This Year — and It’s Working and how it’s all going thus far in 5 Things I Learned Once I Got Proactive About My Mental Health and General Existence.]

Now, I’m leveling…


Left: Los Angeles Wastoid With an Idea for a Book He Says Will Be a Guaranteed Bestseller If He Ever Writes It After Figuring Out How to Connect the Beginning to the End (2015) • Right: Vampire Weekend’s Tour Manager Trying to Get in on a Toast for Someone He Doesn’t Know at a Party Too Loud for His Sensibilities (2019)

Do you know how insanely out of whack your existence has to be for you to huck half your wardrobe, scoop reading glasses you’ve needed for years, and put together three calendars in order to keep track of all the things you always wanted to do but never did?

Let me back up.

In January, I was coming apart at the seams, so I decided to rework myself and the world around me — I quit drinking, I started weekly therapy, I took a hiatus from drugs, I upped my exercise routine, I made a point of getting a good…


Please accept that maybe, just maybe, I want to be single

Illustration: Luciano Lozano/Getty Images

Dear ladies of this particular ancestral shield, who refuse to allow me to live out my days as a bachelor of poise and equanimity:

Ah, my wonderfully charming kinswomen! There are simply not enough holidays in the year for us to gather together and celebrate the richness of life. It is always such a merry occasion to be in your presence, as you all have such a fiery zest for existence. And now, I am straight-up begging you to let me die alone.

Please.

Please be open to the idea that I may want to live, and very well exit…


The good sir and his dunce of a son, both in different kinds of heydays when photographed.

My dad published his first volume of poetry when I was a teenager.

Until then, I was quite unaware, yet totally unsurprised to discover, the man I know as Dad and everyone else knows as John Kilroy wrote poems. My whole life, my dad had been a thoughtful writer-editor type intrigued by the world. It made sense he’d been quietly interpreting his surroundings and those beyond with a curious, meditative pensiveness behind those golden glasses of his.

My mom knew his (I suppose for lack of a better word) “secret,” and one night he presented me, my sister, and my…

Jake Kilroy

Raised by handsome wolves, I mostly write these days. jake.kilroy@gmail.com

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store