“Don’t You Love New York In the Fall?”

I crave the fall in the way some people crave sugar or cocaine; it’s all-consuming, upsets my sleep patterns and causes my spirit to ache. A few months ago in balmy July, I lay on my blanket-less bed watching an episode of Frasier that reminded me of the Macy’s parade. That image combined with the overwhelming summer heat in my apartment caused me to actually cry into my pillow, overcome by my longing for autumn. While you may think I need therapy, I think it makes sense. As soon as the excitement of my mid-June birthday is over, my mind immediately turns to technicolored leaves, pumpkin everything, my fall Gilmore Girls marathon and jackets. Oh jackets, how I love them.

October in New York is the eighth wonder of the world. It’s true what Carrie Bradshaw says in Sex and the City: there’s a moment when the seasons click, a tangible instant when fall arrives in breezy splendor. For me, that moment serves as an annual tactile reminder that God is real and able and good. It’s when the trees change into their best outfits; the ones they save for special occasions. It’s as if God’s toddler took red, orange and gold markers and colored outside the lines of the gridded streets, color spilling everywhere you look. Gourds fill the flower pots in the West Village, Halloween stores bring empty storefronts back to life for a month, and the scent of warm apples fills the air at street fairs and coffee shops.

I live near a university and each year as school comes back into session, I’m reminded how living in New York is a lot like attending a large liberal arts college. The city, much like a university, acts as a conveyor belt that doesn’t slow down, presenting new people and new opportunities in a steady flow. Wide-eyed like Lucy when the chocolate factory forewoman shouts “Let ‘er roll,” I sometimes feel like a perpetual freshman, dizzy from trying to navigate the never-ending bulletin board of things to do otherwise known as Manhattan. It’s a wondrous feeling.

My first night in New York wasn’t nearly as wondrous. I‘d spent the first day of my summer internship shaking hands, pretending to remember people’s names and trying to learn which floor held which office so by the time the sun set, I didn’t know my left from my right. My apartment door was 30 feet from the entrance to Hairspray, something I imagined was God’s way of reminding me I’d done the right thing by coming here, yet in my room that night, I felt so claustrophobic and stranded I had to go up to the roof to get some air. The humidity of that June evening seemed to amplify the white noise of the city, that endless soundtrack of honks and beeps and trains and tires and footsteps. I could see the ambient light from Times Square illuminating the air above it like a flashlight. I could see the rooftops and silhouetted skyscrapers standing tall around me like neon trees and in that moment, I realized just how small I was. I felt dwarfed, incapable and insignificant in this place that breeds giants. I stayed on the roof breathing in the heavy air until worry got the better of me, then I cried myself to sleep.

But time wore on, as it does, and the years were kind to me. After formally moving to the city, I eventually figured it out, something that happened primarily during the fall months when the weather was so beautiful and the scenery so picturesque, I had no choice but to get lost in the concrete jungle of yellow and red leaves. Each time the season rolls around, I discover something new about this city and about myself.

I was a few years into running my own digital magazine when Kevin, a photographer friend of mine, and I were brainstorming who should go on my prestigious fall cover which he’d already committed to shooting. No one else knew this particular month’s cover was prestigious, but it was to me. Vogue may throw all of their golden eggs into their September issue but I threw all of my best effort into the October issue of my small, independent, financially-unviable yet wildly fulfilling, digital magazine.

The reason I poured so much into October was fairly simple: It’s my favorite month in New York so why shouldn’t it be my favorite issue of the magazine as well? It was also the issue in which I focused exclusively on Bro­­adway performers, which led Kevin to mentioning his friend Alan Cumming as a possibility. I’d interviewed performers from dozens of Broadway shows by that point, the Lion Kings and Hairsprays and Wickeds, all of which felt surreal. As a boy from Texas, I never dreamed I’d sit on a park bench next to an Elphaba but there we sat, eating Shake Shack in Madison Square Park, talking like casual friends. Yet with all the opportunities that’d opened for me, I’d never interviewed anyone as established as Alan.

I started the magazine as a way to fill the creative void in my otherwise dull 9-5 life and progressively, it became bigger and more known in certain circles. It opened doors for me to meet artists I admired and become acquainted with people I’d otherwise never know. I learned how to navigate social situations with people of every industry, how to carry myself professionally even when I was in the fake-it-til-you-make-it stage, and every interview was as much an exercise in learning about myself as it was learning about someone else.

Soon after he pitched the idea, Kevin told me Alan was game for the feature and a shoot date was decided. We thought a simple photo shoot in Central Park made the most sense in that it gave us location options within the same section of the park. I ran a very small ship—no giant setups or crews or catering or anything seen in The Devil Wears Prada—so it would just be me, Alan, Kevin, and his photography assistant wandering freely around Central Park for a morning. Only in New York does this sort of magic materialize.

It’s not that I don’t admire the goings-on of large scale publications and the money they’re able to spend on photoshoots, it’s just that I understood I wasn’t going to be able to compete with those magazines. That and the decline of print subscriptions in favor of free online information made the goal of being the next Rolling Stone laughable. However, I could be the best version of my own idea and collaborate with people I looked up to. So we kept things simple and intimate, pretense-free.

Alan arrived in a cabno entourage, no publicists, just himselfwearing a black sweater, denim trench coat and overalls of the same material that halfway resembled lederhosen. His black and silver hair was tousled and disheveled in a way I could never get away with and his smile lit up his face with the playfulness of a boy half his age. He was as bad ass and as fabulous as anyone I’d ever met.

If you’ve ever seen his work on screen or on stage, you know he’s a formidable talent. More than that, he has the ability to be a forceful, dominating presence when he’s acting; someone who speaks with heft. I introduced myself expecting to encounter that same heft, but I quickly realized Alan is gentile and soft-spoken, both unassuming and friendly. I’d interviewed a handful of notable musicians by that point and found that some of them carried themselves as if the world owed them something. They’d bought into their own hype and as a result, they had extremely lofty opinions of themselves. Alan was the opposite, able to switch in-and-out of his photoshoot face and his charming just-one-of-the-guys face with ease.

The four of us wandered around Central Park near the mid-70s streets for about an hour. Alan posed like a pro and I listened intently as he told us stories in his demure Scottish brogue about the workings on The Good Wife, my favorite show, and the fallout from the movie star who was set to star in Cabaret with him but dropped out the day before the announcement because she was scared. Years earlier, he’d won the Tony Award for his portrayal of Emcee and now both that production and the star who’d made it a success were coming back to Broadway. It was big news at the time and as we wandered through the early changing leaves, he talked about preparing for the role again.

I’d expected to meet the Alan I’d seen onscreen–the celebrity/movie star/Tony winner–and I’d been thinking, rethinking and overthinking this morning for weeks. Yet as he spoke, he put my anxious mind at rest by being the funny, well-learned, curious person he is. The celebrity aura I’d fabricated fell away and he became just Alan, a very talented actor with whom I was lucky to spend a morning.

For denizens of New York, celebrity sightings are as old hat as ducking into Duane Reade when it starts to rain. So You Think You Can Dance winners and Tony nominees blend together with lawyers and mothers wearing Manolos. It’s another of the wonders of this great city. The nameless privacy the park provided us during our shoot disappeared as we walked down 72nd street toward a coffee shop for the actual interview. One woman did a double take as Alan passed her and she shouted back, “Hey! You’re that guy! I love you!” He smiled and gave a kind wave. Another man, probably only a handful of years older than myself, stopped to thank him, telling him his work is what made him want to be an actor. Again, Alan was cordial and kind, in no way dismissive or self-indulgent.

Still, in my head I thought, This is the guy who faced off with James Bond and Wolverine! He dressed Carrie Bradshaw and hung out with the Spice Girls! From that vantage point, he had every reason to feel special and a step above the rest of us. But that’s not how he carried himself at all. Walking down the street alongside him, I again felt like the perennial freshman having learned something. The preconceived ideas we might have about someone, famous or otherwise, aren’t necessarily true. We’re told this when we’re young but that day, it stuck.

During our interview, Alan said, “For me, returning to that role [Emcee], I first did it when I was 28 and I felt like I was having a nervous breakdown, and then I did it when I was 33 and I felt sexy, confident and in my prime. Now I’m going back to it at 48 and I still feel sexy, confident and in my prime, but I’m older and wiser and I think it’ll have different layers to it. It’s one of those roles that’s not really a part. It’s not really a fully formed character and you have to make it what you will.”

Kinda like New York.

How his experience with this role mirrored my year-by-year experience with this city was astonishing, like something written for a screenplay. That lonely first night in the city when I felt like I was having a nervous breakdown felt so far away now in my 30s, walking through New York nights with confidence and in my prime. I’ve learned walking down the street isn’t just walking down the street here: it’s an allowance for adventure–if that’s what you make it. That’s an addictive feeling.

When I moved to the city, my friend Rachael told me, “You’ve been saying you were going to move up there, and you did it. You’re living your dream.” That’s when I realized I actually was. It’s funny how we need people to spell it out for us sometimes. I was living my dream. I am living my dream. As insurmountable as it would seem at times to feel like I was even a small part of the greatest city in the world, it’s become everything I’ve ever wanted it to be. Who could’ve imagined I’d be having coffee with a Tony winner on a weekday and a few weeks later he’d be on the cover of a magazine that never existed before I moved here and started it? A magazine read in 150 countries. A magazine that let me and my friends create whatever we wanted, do photoshoots with people we admired and add our voices of positive possibility to an increasingly negative digital world. Certainly not me, but there I was. Here I am. It’s all a far cry from that claustrophobic summer night on a rooftop and as such, every year during the fall, I’m reminded that the adventure becomes even better. I get to spend my life being a perpetual freshman in New York City, learning, exploring and everyday becoming a more fully formed me.

“Don’t you love New York in the fall?” That’s what Tom Hanks asks Meg Ryan in You’ve Got Mail. My mental romance with autumn in New York began with that movie—with bouquets of freshly sharpened pencils and bookstores and tall decaf cappuccinos—but what a supreme joy it’s been to discover the movie version doesn’t hold a candle to the real thing.


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