Written by Skip Montross

“So I was out last night with my friend Alan.”

It’s a sentence I use often when conversing with co-workers and acquaintances.

“We had some drinks and then saw a movie,” I will follow. Then comes a story about the drinks portion of the evening. A funny story. Perhaps a charming anecdote. At one of our recent film excursions Alan made a joke a few moments into the feature. As a goofy but harmless teacher stood on the screen greeting the students in his school, Alan looked at me and said, “It’s Mr. M!” I couldn’t help but share a pretty significant laugh. You see, I work in an inner-city school and “Mr. M” is what my students know me as. The man on the screen was not a bad representation of my presence in my school. Goofy, middle aged, undeniably terrible jokes… yet somehow ingratiated with and appreciated by his students. I couldn’t help but chuckle as he hit the nail on the head. I turned to him and said “You’re one of my favorite people to watch movies with.” He replied with “Well, duh!?!” as only he could. That’s Alan Ilagan in a nutshell. That is my friend.

For several months he’s been after me to complete my second guest post for his infamous blog. I was happy to do so. But saying I will do a task is very easy for me. Actually fulfilling said task is much harder. Forget about on time. Writing is an endeavor that I enjoy. And it is an endeavor that I am told I have a gift for. Sitting down to put pen to paper nonetheless is a task. For me at least.

When it comes to writing the prospect of a looming piece I find it daunting. My mind swarms with ideas. Far too many to count. An ocean of swarming fish. Each an idea desperate to take the bait. But with the looming endless horizon laid out before me I am unable to let cast my line and reel it in. I am lost in the abyss of potential. Sitting on the deck that is the rocking boat of my mind thirsting for inspiration. As is life, sometimes inspiration comes from the queerest of places. In this instance… that is my friend Alan.

When Alan and I talked of this article it was often over drinks before a film. Typically we sit together at a bar speaking far too loudly than is comfortable for those around us. He’ll have a Negroni and fume over the bartender’s inability to make it properly despite having grilled Alan beforehand about the ingredients and preparation. He will then laugh under his breath at me as I attempt to impart my “bartender wisdom” on our drink server in an obvious display of contempt. I will typically sip the bar’s most expensive Scotch and their cheapest beer betraying my peculiar dichotomy. This has become a richly appreciated and comforting tradition. Drinks and then a movie.

I can’t really overstate how much I appreciate these get-togethers. I find them to be a respite. A welcome retreat from the simple but very real pressures of life. There are, of course, the drinks and the movies. A welcome frosty cold bottle of beer in front of a long-awaited Summer Blockbuster; a belly-warming 12-year-old MacCallan before the winter’s surefire Oscar Contender. But much more than that is this: our conversations.

Conversations that are sometimes perfectly shallow and pedantic. Where we might argue over the nature of some meaningless pop culture topic. How we viewed a particular song or show or film. Where I might laugh at how he has no earthly idea who LeBron James is, or how he finds it sad that I only know Patti LuPone as the mom from “Life Goes On.”

Conversations that are sometimes downright hysterical. Some of the times in which I’ve laughed hardest in my life were at moments shared around a bar or high-top table. Moments where we discussed some of the most terrible people life forced us to work or interact with. As someone who has dabbled in stand-up comedy, who has always prided myself on my ability to make people laugh, I’ve never had a better audience than Alan with a couple of drinks in him.

Conversations that are sometimes as deep as the trenches of the seas. Moments when we might discuss the more somber and terrifying prospects of life; relationships, families, love, life, death. Conversations as deep and true as earnest friendship.

It’s not always just the two of us. Often we’re joined by a guest conversationalist. Our favorite being Andy. Not the vaunted VanWagenen, Alan’s Better Half. But rather Mr. Pinchbeck. A man who adds his own unique vantage point. An always welcome third-party who balances our takes with his own, representing a view we hadn’t yet seen.

When we talk we find something that is missing from our own myopic view: perspective. A perspective that is not our own. Even though we might share a great number of similar views be it politically, philosophically or otherwise there are still a great deal of experiences that we have that are unique to us. Alan has lived a life as a minority and a gay man that I would never have known nor understand were it not for our friendship. I like to think that I present to him an inside account that is the day-to-day workings of a traditional straight married white man that he might not experience otherwise. By sharing our experiences through the rich tapestry that is woven over many nights of conversations, we better one another and help to expand our worldview.

I am reminded of a night last June. We were in Boston. Inside of Alan’s beautiful condo in the Back Bay. It was the last night nearing the end of our annual Red Sox weekend. A tradition now entering its 4thyear. We had shared a weekend laden with food, drink, memories, and most importantly world-class conversations. Bags packed, calling it a night, readied for the morning commute back to New York, Alan turned and said to me, “I hope we can do this when we’re 80.” I do too, my friend… I do too.

I can’t help but to wonder… wouldn’t these conversations make a phenomenal podcast?