The inherent subjectivity of cool makes speaking on what makes something cool hard to formally discuss. It’s impossible to keep up; to know what you should know and and be where you need to be. Lucky for us, Tyler Bainbridge is here to fill us in. As founder of the cult independent newsletter Perfectly Imperfect, which shares “a taste of someone’s taste” three times a week through Substack, Bainbridge has made it his purpose to give a glimpse into the New York-centric milieu one recommendation at a time.

Each Perfectly Imperfect letter contains a self-portrait of the person in conversation with a few bullet points and explanations about what they can’t stop thinking about. Some past features include internet writer and FLAUNT featuree Rayne Fisher-Quann and her guide to the perfect karaoke song, how Michael Imperioli finds real despair with R.W. Fassbinder’s In a Year of 13 Moons, what expensive underwear Charli XCX is wearing, and how Ayo Edebiri is “being optimistic, randomly...” Bainbridge explains, “I kind of view it as an unconventional profile, in that there’s no interview at all. But you’re learning about someone and unplugging and talking about what they’re up to. The actual piece is a very unfiltered pure view of what they wanted to say. It’s not cut up at all.” On Perfectly Imperfect’s page, you’ll find an established celebrity sitting next to Brooklyn’s newest noise band, both treated with the same format and adoration.

While a listicle of what’s cool might seem temporal in nature, the newsletter’s nearly 400 guests and over 3,000 recommendations serve as testimonials of what meant something at a certain time, encapsulating specific pockets of New York that have come and gone or have simply faded out. Bainbridge reflects, “I even look back on certain periods that we’ve been doing a new side of that feel already very like, ‘Wow, that was like a distinct, weird little moment in New York.’ I think the longer we do the newsletter, the more we’ll have a capsule effect.”

As time progresses, we might not remember who we were in 2023. But when bar italia comes on the radio someday we will think of the joy and strife that came with the timing of the new release. If each melody is carefully packaged with the essence of time, Bainbridge started his playlist, “The New Sound,” to conserve and document the present. This year he shared “The Best Songs of 2023”—the perfect place to escape the algorithm, and even includes artists featured in this very issue. And while Spotify might steal this anti-genre, only to name it as a feeling (or a vibe, god forbid) Bainbridge’s playlist actually preserves a memory. It is here where Artificial Intelligence will always falter. AI can never replicate the intention and purity of a true friend’s recommendation.

For all things esoteric and niche, Bainbridge has started a sister site, PI.FYI, which he defines as “a place where people talk about what they love and want you to love.” A couple of days after we speak, Bainbridge sends me a link to the now invite-only beta site and app currently available to premium subscribers, and it feels as if I’ve been touched by an angel. As I scroll, it seems like a mix between “Letterboxd, early internet forums, and Myspace,” where people can share what they are into and ask for recommendations from their friends. While some are true to heart, earnest recs about slushwave or declarations of the best New York congee spots, I also see a recommendation or maybe a reminder of the joy of “BEING PURE OF HEART.” The post says we need to “bring back conviction and child like wonder.” Directly after, someone asks: “CAN YOU OVERDOSE ON TUMS?” It’s funny, it’s abstract, and it’s real.

“I think people were craving that a bit.” And with the breadth of his interviews with some of New York’s most unhinged, he has yet to pull back on any reigns. “I’m always wondering, is this too far? Is this not too far? But ultimately, I think it’s cool to be able to push the boundaries, with an independent publication, just having no one to say no.” He continues, “But I think just like diverse points of view from people that aren’t media trained, even the journalist, is interesting.”

So, are we known only by what we know and what we like? Is there more to us than our favorite band or dirty alt-lit story at the moment? As I am writing this piece and contemplating what makes me, well me, I see a recommendation on Bainbridge’s PI.FYI profile. It reads: “Earlier this year I set out to do some kind of Caveh-esq [sic] experiment of writing one recommendation every single day, with the goal of building some kind of weird portrait of myself in public. It’s almost like journaling.”

And it makes you think that there is something to be said on recommending. That it’s more than a statement saying that you know a place, but more that you are here. You’ve been alive long enough to know what you love and appreciate, and you want to share it in the hopes that it deposits onto the recipient, whatever feeling it brought to you. And while gatekeeping might have its place (can’t think where), Bainbridge shares that it does not belong in the world of Perfectly Imperfect. After all, we are here under the same moon, just trying to experience what life has to offer. And with what little time we have, we can only trust the ones we hold dear... and whoever Perfectly Imperfect features next, of course. 

Photographed by Paige MacCready

Styled by Jenny Nayoung Kim

Written by Bree Castillo

Grooming: Glenda Thompson

Production Assistant: Annie Bush

Location: Hotel Dena

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