Did he vote? The man I envisioned myself with for the long-term definitely did.
"I'll make an effort," he told me, rather apathetically, but texted later that night asking about my polling experience.
"So, did you vote for Trump?" he wondered.
"You know it," I joked.
Come Friday, when I arrived at the bar, I was pleased to see he looked every bit like his pictures and seemed even more nervous than I was. He appeared far more conservative than I'd pegged him - wearing a Ralph Lauren button-up and standard Bostonian loafers - which I found oddly refreshing ... until 20 minutes into our date when he declared that Donald Trump was the only presidential candidate who could turn this country around.
"Are you serious?" I said, scanning the bar to see if anyone might've overheard.
He was.
As I asked him more questions about his politics, I was simultaneously horrified and riveted. Here in Boston, the crown gem of this left-leaning commonwealth and birthplace of the American Revolution, stumbling across a Republican was not something I'd anticipated.
I mean, I'd suspected they were here, walking among us. But surely not in my demographic of single, college-educated 30-somethings.
I'd mistaken his earlier Tinder message about voting for Trump as a joke because Trump is a joke - a scary, racist charlatan. Only it turns out that people actually like him, and my date was one of those people.
"Were you liking me up until Trump?" he asked.
I nodded. Only I still kind of liked him.
I'll be the first to admit that I'm deeply flawed. With other men, I've ignored red flags of alcoholism and other obvious warnings of incompatibility or criminal behaviour.
But I couldn't yet decide if this guy's opposing political preference was a red flag because this was my first time clicking with the other side. I wanted to know more about him and, most important, why he supported Trump.
So we veered into the kind of ideological conversations typically reserved for later dates.
We debated and raised our voices. We alarmed surrounding bar patrons with our heated arguing. It was pretty hot, this first-date rule-breaking. So rarely, I find, are singles this honest on a first date because we want the other person to like us. But here it was, our deeply held opposing beliefs, laid bare.
He wasn't dumb or uninformed. While he'd twice voted for Obama, he said, he'd come to support Trump because he was so traumatised by the Boston Marathon bombings and homeland terrorism that he worried about the safety of his future wife and children.
We could've argued forever, but eventually I insisted that we talk about something we could agree on. So we landed on music, specifically Billy Joel.
"I'll make a bet with you," I suggested, bolstered by a few margaritas. "If I know more lyrics to We Didn't Start the Fire than you, you have to vote Democrat."
"And if I win, you have to kiss me," he countered.
Hesitantly, I agreed. We went back to his place, queued up the song and had ourselves a sing-off.
While screeching along about "birth control Ho Chi Minh Richard Nixon back again", I realised that the irony of the song was lost on my date. Trump was stoking the fire with his vitriol and racism.
And while politics aren't everything, I realised they're a pretty big deal. If my years of dating have taught me anything, it's that I was never going to change this guy. I was also never going to end up with him.
And I lost our little bet.
With my Uber driver idling outside, I held him close in the foyer of his apartment building and kissed him.
I would never see him again.
- Bloomberg
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