A Date With a Palestinian

Regulars in my dating vault already know the horror stories. Boston men who hold eye contact just long enough to ask if you want to split the check on a first date. Men raised on a steady diet of postmodern theory until every last primal instinct got theorized out of them, replaced with avoidance, hedging, and the faint, apologetic ghost of what used to be masculine energy.

I keep wondering what happened to the primal mechanics of nature. What happened to the instinct to pursue, to be a man a woman can actually lean her weight on, the one who drives, who plans, who handles things, who makes room for a woman to fall back into her own feminine energy instead of clawing her way through his. The kind of energy that gets repaid in softness, in trust, in love, instead of this exhausting, humiliating negotiation just to get someone to try.

It was exactly this that put me on a plane for a two-week escape from Boston, desperate for a break from all that progressive exhaustion. I wanted somewhere I could work, step outside my usual narrative, meet people, learn to surf. Portugal seemed like the obvious answer, so I booked two weeks of backpacking, hopping between guesthouses along the coast.

It wasn’t the Europe I remembered from years ago living in England. The streets smelled; thousands of tourists obscured the actual residents, many of whom were from Pakistan, Morocco, and Bangladesh; it almost felt like that beneath the tourist surface lay a second city, visible only if you looked past the crowds: men loitering in alleyways, watching, stepping closer; women who appeared and vanished in black burqas as the light dropped.

I wondered if I was seeing things clearly, or just too sensitized by my own writing to trust my eyes. So most nights I went looking for an answer on the dance floor, salsa and bachata socials scattered across Lisbon, and let the locals talk. They handed me no-go zone stories the way you hand over a weather report, flat, familiar, already grieved. Sharia creeping in by inches. A government that had quietly stopped protecting its own. They confessed it with something close to heartbreak, the particular grief of people watching their city get replaced under their own feet. I wanted to walk those streets myself and see it, but they told me plainly, dressed the way I dress, I wouldn’t make it a block. So I didn’t go. I didn’t need to. Even from inside the postcard version of the city, crowded with tourists and oat-milk lattes, the demographic tide was unmistakable.

European cafe culture was something I'd genuinely missed. Sitting for hours with a laptop or a deck of cards, letting the conversation drift to the next table, until somehow you're pulled into someone's dinner plans, a late-night party, or just talking for hours with a stranger from the other side of the planet. That's my favorite part of traveling. That kind of effortless connection feels almost extinct in hyper-efficient places, where wasting time is treated as a moral failure. Fifteen years in Boston, and the check still lands the second the last bite disappears, the table cleared out from under you before the conversation can breathe. Where I come from, a meal is an excuse to linger. Here, it's a transaction with a turnover quota, and I have never once made peace with it.

I have to say, wonderful things happened to me on this trip. I spent nights laughing until my ribs ached, talked with strangers for hours, and remembered the amazing fact I had almost forgotten since October 7: at my core, I am a very happy person.

Then came the afternoon at the organic cafe, a polished, nomad-centric workspace where a single latte runs ten dollars, and breakfast arrives artfully plated on artisan stoneware. The open-plan workspace was alive with digital nomads from every corner of the globe. That was when I reached into my bag and realized I had left my headphones back at the guesthouse. Near me sat a man in his mid-thirties, dark-featured, stylishly dressed with a subtle hipster edge. He caught my brief panic and looked up. “Did you lose something?” he asked. “My headphones,” I said, already gathering my things. “I have to run back to the guesthouse.”

He looked at me with a quiet, deliberate smile. “If you won’t come back, I live in this guesthouse.” He gave me the name. “A few of us are hanging out outside later. Nice bar, good people. You should join. We can talk and get to know each other.” He smiled again.

“Sure,” I said. Why not? I’ll be there. Sitting in that sunlit cafe, I had no idea exactly what I’d just agreed to. A date with an Arab. Except not just any Arab, one of the ones who insist on calling themselves Palestinian.

A date with a Palestinian

By the time I made it back to the guesthouse, late afternoon was already giving way to dusk. A handful of people sat on a weather-beaten wooden bench and a makeshift picnic table, their voices drifting through the warm air. The topic, inevitably, was surfing. This stretch of the Portuguese coast was a mecca for nomads, people drawn by the siren call of sun, ocean, and the promise of a life measured in swell charts and tides.

I sat down and joined in, sharing my initiation into the ritual: how I had wrestled with the crushing weight of a surfboard all the way to the shoreline, every nerve in my body screaming to turn back and ditch the lesson. But then came that split second when I stood on the board for the first time, defying every panicked instinct my brain had spent hours building. It was a flash of pure, unadulterated triumph. Suddenly, every brutal wipeout, every bruised limb, and every gulp of salt water felt like a small victory of willpower.

We mapped out potential routes across Portugal, debating whether to head north to Porto, wander through the fairy-tale mist of Sintra, or chase the sun down to the Algarve. Classic travelers’ talk. After about 30 minutes, the group stood up. They had plans to meet another friend at a nearby winery and made their exit, leaving just the two of us on that wooden bench. The Portuguese night was soft and warm. A single bottle of wine rested between us. What I had no way of knowing then was that we had grown up just a few hours’ drive apart.

“Did you end up finding your headphones?” he asked, leaning in slightly. “I did,” I said with a faint smile. “Though I never made it back to the cafe. My roommate at the guesthouse dragged me to a live music show by the water instead.” He studied my face in the low light, the way you’d read a menu in a language you almost know. “Where are you from, anyway?” “I live in Boston,” I said, smooth as a rehearsed line, because it was. Something in him relaxed, satisfied, like a theory confirmed. “I knew it. Your accent is so American.”

I offered a quiet, internal smirk. To a non-native ear, my accent certainly sounded American, a byproduct of years spent deliberately refining every syllable, but any actual American would pick up on my cadence within thirty seconds, catching the subtle foreign inflections and the occasional slip in grammar.

“And you?” I asked, turning the question back on him. “Where are you from?” Grateful, for once, that asking is still a legal question out here, with no blue-haired activist lurking to scream about microaggressions. “I’m from Palestine,” he said, plainly, as if it cost him nothing. The word hung there, sudden and sharp, and for a second it emptied the air from my lungs. Palestine. I kept my face perfectly still and took a slow breath. “Gaza, or the West Bank?”

“No,” he said, giving me a brief approving nod, as if I’d passed some minor geography quiz. "I mean Palestine, the part within what people call Israel. I'm from a small village up north. Rama."

I stared at the wine glass for what felt like an eternity. Long, deliberate seconds. Then I lifted it with a flair that would have made a stage actress proud. I let a smile play on my lips, took a breath so deep it anchored me to the spot, and said, with deliberate clarity: “Free Palestine.” His smile returned instantly, breaking the tension. “Free Palestine,” he replied, his voice a mirror to my own. We clinked glasses. The sharp chime echoed as I took another slow breath. It was, quite possibly, the first time I had ever let those words cross my lips.

Three glasses of wine in, and somehow my mind had never been sharper. I needed to understand this, not intellectually, but the way you understand a bruise, from the inside, by pressing on it.

Here was a man sitting across from me, an Israeli citizen, born on the same soil I was and raised under the same sky. Yet while so many other Arabs in Israel had made their peace with the Jewish presence in Israel, their ancestral homeland, and chose to see themselves as Israeli-Arab, this man had chosen to erase the name of the country he was born into, to call it by another name, and to become, body and soul, Palestinian.

What I learned that night, the truths he handed over as easily as he refilled his own glass, changed the way I’ll see a whole segment of the people living next to me for the rest of my life. I think I just figured out how you build a nation inside someone else’s walls, without ever moving a single stone. Pour yourself a glass of wine. Come sit with me. I want to take you inside the mind of a “Palestinian.”