I was at this dinner party, the kind of gathering where people wear sweaters that cost more than my monthly rent but look like they were woven by monks in the Himalayas. The kind of party where the cheese plate has items so exotic they might actually be experimental fungi, and the wine is organic—which, by the way, is supposed to taste cleaner, but to me it just tastes like wine that needs therapy.
Anyway, I’m sitting there, nodding like a man who knows something about Malbecs, when I notice her—across the table. She’s laughing. At first I think she’s laughing at me, which is not an uncommon experience, but then I realize it’s one of my jokes. Or at least I think it is. There’s a 40 percent chance it was indigestion. I tell myself it doesn’t matter—it’s still a reaction, right? But here’s the problem: my brain is a terrorist. The second I consider opening my mouth, it launches an attack. “Don’t say anything. You’ll ruin it. Remember the last time you tried? Disaster.”
And they’re right, my brain voices. History has provided an extensive archive of my failures. If my love life were a museum, the exhibits would be “The Hall of Awkward Silences,” “The Gallery of Botched Compliments,” and “The Wing of Near-Misses.” It’s less a romantic biography than a cautionary tale for men who confuse hesitation with strategy.
I tell myself, “Play it cool. Wait for the perfect opening.” Except I’ve been waiting for that perfect opening since adolescence, and it never comes. I’m like a man at a crosswalk who refuses to move until every single car in New York stops driving forever.
That’s when the vignettes begin, the reels of memory, little humiliations playing on repeat. Because every time I almost take a chance, I don’t. I stall. I retreat. And the story ends before it even begins.
The Café Girl
There was the café girl in Beacon. Six months of my life spent ordering espressos I didn’t want and biscotti that could’ve doubled as drywall, just to orbit around her presence. My entire digestive system was collateral damage. And the day I finally rehearsed the line—“So, uh, do you like working here?”—I learned she’d quit. Moved to Oregon. The barista told me in the same tone you’d use to say, “It might rain on Saturday.” I walked home carrying a biscotto like it was a death certificate.
The Subway Stranger
Then there was the woman on the subway in Brooklyn. She sat across from me, reading a novel whose title I couldn’t quite see. But she laughed at something on the page, and I thought, God, if I were a braver man, I’d marry her right now between stops. My plan was to casually lean forward and ask, “Good book?”—which, in retrospect, is less a question and more an assault on conversation. Before I could open my mouth, the train lurched, I lost my balance, and landed in the lap of a man who smelled like wet socks. By the time I regained dignity, she was gone, probably telling her friends about “the flailing subway acrobat.”
The Museum Date
I did once manage to ask someone out. We went to the Dia in Beacon where we stood in front of a painting that looked like someone sneezed ink onto a canvas. She said it made her feel like “a grain of sand in an infinite desert.” I said, “Exactly,” though really, I was just wondering how long it would take to find a bathroom. Two weeks later she ghosted me. Vanished. Except she still likes pictures of Labradors on my Instagram, which is the emotional equivalent of leaving breadcrumbs outside the cage.
The Grocery Store Encounter
There was also a woman in the produce aisle at Stop and Shop in Poughkeepsie. She asked if the avocado I was holding was ripe, and my brain panicked and replied, “It depends on your definition of ripe.” Who says that? She smiled politely and moved on, probably thinking I was a fruit critic on probation. I later saw her at the checkout line, but I couldn’t bring myself to wave. I went home and googled “how to talk about avocados without sounding insane.”
The Rainstorm
And once, in a rainstorm, I offered my umbrella to a stranger while shooting a wedding in Rhinebeck NY. It felt like a cinematic moment—the kind of gesture that would lead to coffee, then laughter, then a montage of us bicycling through a park. Instead, she said, “No thanks, I like the rain,” and ran off like a woodland creature. I stood there, drenched, holding an umbrella like the world’s least convincing superhero.
The pattern is always the same: hesitation, paralysis, silence. Love, for me, is Russian roulette, except every chamber is loaded. And yet… what if? What if the woman at the dinner party was laughing at me, and not at her indigestion? What if the subway stranger had looked up, seen me not as a man falling into another man’s lap, but as someone worth talking to? What if the café girl had stayed just one more week?
It’s absurd, I know. I spend my life waiting for guarantees, like a man who refuses to swim until someone drains the ocean. But if I keep waiting, all I’ll ever have are near-misses and bad biscotti.
So maybe the real risk isn’t rejection at all. Maybe the real risk is disappearing into my own hesitation—watching chances pass by like trains I’m too nervous to board.
And so, I sit here, glass of organic wine in hand, rehearsing lines I’ll never say, while the universe, in all its infinite patience, waits for me to take just one imperfect, catastrophic, absolutely necessary chance.
