Before 2016 I Dated Republicans Without Much Shame

As I watched Donald Trump win the presidency on November 8th, 2016, I didn’t know that it meant my days of sleeping with Republicans were over. Why? For a start, it took me a few days to even accept the election results. Furthermore, I’d never sought out Republicans for intimacy-related reasons—it was one of those things that just happened, from time to time. But if I’m being honest with myself, the real reason is that I didn’t even realize a line in the sand existed until someone else articulated it.

Before 2016, I dated Republicans without much shame. I didn’t agree with them politically, but I subscribed to the mathematically-sound belief that the wider your net, the more likely you are to get a boyfriend. Besides, I thought politics was private; how we vote is anonymous, after all. However, on a date in early 2018, when a man told me his only deal breaker was that he wouldn’t date a Trump voter, I responded with, “well, of course I wouldn’t date a Trump voter.” And I meant it. Which meant that somewhere along the way, something had shifted.

I hadn’t fully understood why until I read Cecilia Rabess’ phenomenal novel Everything’s Fine—the story of Jess, a young, liberal Black woman and Josh, a young, conservative white guy. They meet in college, get to know each other on the trading floor of Goldman Sachs, and begin dating while she works for him at a hedge fund. 

Everything’s Fine was flooded with bad reviews before it came out. Readers found the premise—that a Black woman would date a racist white man—racist. I’m a white woman; it’s not up to me to decide what’s racist, but I don’t condone reviewing a book before reading it. At the same time, I can conceive of a book description so racist that the book itself should be discredited—which is why this controversy made me curious. So curious, in fact, that I bought the book. 

I’m glad I did, because I loved it. The criticism isn’t unfounded; Josh makes insensitive and ignorant comments about race throughout, which qualifies him as a racist. And yet, I’m of the opinion that all white people in this country (myself included) have made insensitive and ignorant comments about race at some point—and in this case, I thought it was fair to leave it up to Jess to choose whether or not to forgive. 

Jess, for her part, isn’t perfect either. She feels guilty walking by Occupy Wall Street protestors on her way to her Goldman Sachs job every day, but she changes nothing. She benefits from Josh’s wealth and tolerates his behavior for years. 

And I related to Jess’ dilemma. Like her, I often find myself torn between an opposition to capitalism and the necessary acknowledgment that it benefits me. And I related to her romantic predicament: existing in a relationship that looks terrible from the outside (Jess’ friends describe Josh as “toxic” and even question if it’s ethical for Jess to date him), while knowing there’s something there my friends can’t see. But as Josh continued to offend, and as her political views developed, tested by the inequities of the so-called real world, I began to wonder: was she ever going to draw the line with him?

She reaches the end of her rope in Summer 2016, in a moment that’s very specific to their relationship, and yet so glaringly familiar. Searching for a lost item in their apartment, she discovers Josh owns a MAGA hat. And then, Jess is done.

And as she’s breaking up with him, Josh snaps too. He says aloud what Jess has been fearing for years: that she’s a hypocrite. He claims she’s a beneficiary of the same power structures she theoretically opposes. He’s not wrong, but at the same time, Jess is also a victim of these power structures—she’s the recipient of routine racism and sexism on Wall Street. Rabess asks us not to oversimplify oppression—a person can be on both ends.

More convincingly, Josh says it’s unfair for Jess to hold his Trump support against him, as he’s never hidden who he was. She already knew he was a registered Republican, that he’s always voted for Republicans. He voted for Mitt Romney, he works at a hedge fund, he owns a $4 million apartment, and he’s opposed to most social welfare programs. He hasn’t changed.

He’s once again not wrong; given everything we know about Josh, his support of Trump is expected. Here, I recognized the innate hypocrisy of my own line. Is a Romney voter much better than a Trump voter? They are largely the same people, and I mean that as a statistical truth, not a moral assertion. Most Romney voters voted for Trump, and the ones who didn’t were largely educated wealthy white professionals. Republicans vote for Republican candidates; that’s one of their defining qualities. To this very day, 91 charges later, 70% of registered Republicans are still with Trump.

And yet, even if Josh’s support is to be expected, even if it’s in line with everything he’s ever done, and even though I remember exactly what was happening in Summer 2016, I still gasped when Jess found the hat. But why? Why was it different? Why was this Jess’ line? Why is it mine?

On the one hand, it’s obvious. Because it’s Donald Trump. Trump is and was so blatantly racist and misogynistic that no Black woman should have to explain why they dumped their white boyfriend for supporting him. Nor any woman in general. Even though Josh was a Romney voter, Trump is so much worse. 

Furthermore, when Josh voted for Romney, he wasn’t dating Jess. Perhaps Jess wanted to think Josh had adjusted his views merely by osmosis, even though he never caved during any of their arguments. Here, again, I related strongly. We all like to think we can influence our partner’s political views, and sometimes we can. In 2014, I successfully convinced my conservative investment banker boyfriend that his time was too valuable to waste voting. That was the only time, though.

And Jess didn’t dump Josh when he told her he was voting for Trump, she dumped him when she found the red hat. Josh tries to argue it’s “just a hat.” But of course it’s not just the hat, it’s his show of enthusiasm the hat represents. As Rabess writes:

“It makes Jess think of racism and hatred and systemic inequality, and the Ku Klux Klan, and plantation-wedding Pinterest boards, and lynchings, and George Zimmerman, and the Central Park Five, and redlining, and gerrymandering and the Southern strategy, and decades of propaganda and Fox News and conservative radio, and rabid evangelicals, and rape and pillage and plunder and plutocracy and money in politics and the dumbing down of civil discourse and domestic terrorism and white nationalists and school shootings and the growing fear of a nonwhite, non-English-speaking majority and the slow death of the social safety net….and Josh—now it makes her think of Josh.”

It’s not just me and Jess. Politics is a common line to draw in romantic relationships, in theory. I wouldn’t date anyone who I know definitely voted for Trump—and 71% of registered Democrats say the same. And even though I have more firm lines than I used to, it’s still my preference to know less about someone’s politics early on in the relationship. For example, I’m grateful I was already in love with my partner by the time he revealed he voted for Gary Johnson. Relationships are hard enough without adding politics in. 

But Jess’ line was with Trump himself, not Josh’s politics. And so—I had to admit—was mine. Did Trump change what it means to date a Republican? What you’re conceding when you do? 

On the one hand, Trump has said and done so many abhorrent things that it feels like a no-brainer. It would be impossible to date anyone who even tries to defend him. There’s a reason the 2017 Women’s March, the day after his inauguration, was the largest single-day protest in our country’s history. Supporting Trump feels like a hole so deep it would be impossible for a relationship to climb out intact. 

On the other hand, maybe I’m just using Trump’s specifics as an excuse. It often feels like “Never Trump” Republicans just want us to go back to a time when Republicans were polite about their tacit support for income inequality. Maybe I just want absolution for the Republicans I dated pre-2016. Maybe a more progressive person would tell me the same thing Josh told Jess: Republicans vote for Republicans.

Everything’s Fine doesn’t end when Jess dumps Josh. He goes to great lengths to win her back—he shows up in her hometown, even though she’s ignored his calls for months, and at one point, he even offers to sacrifice his job to save hers. She remains on the fence. Indeed, she’s as undecided after their breakup as she was during their relationship. 

I don’t hold this indecision against her. I don’t hold it against anyone for breaking their own rules, for crossing their own lines. Whatever we say we care about when it comes to our partners’ politics often goes out the window in the face of attraction. I say I wouldn’t sleep with a Trump voter—and to my knowledge I haven’t—but maybe that’s because an attractive enough Trump voter hasn’t hit on me (it brings me no joy to say this, but some Republicans are hot). Dating may compel us to compromise our political values, but then again, so does politics itself. I could fill a book with abhorrent things Democratic politicians I’ve voted for have said or done; I regret none of those votes. It’s not as though I had infinite choices. 

Furthermore, it might not be helpful to draw political lines in romance. Sometimes, I feel like my refusal to date a Trump voter is self-indulgent, for the same reason I tend to roll my eyes when the privileged discuss how they’ll move to Canada if Trump is reelected; the people with the resources to move countries are exactly the ones who don’t need to worry. Maybe a white lady swiping left on moderates is false martyrdom; making it about me when it doesn’t need to be. Maybe choosing to let politics affect one’s personal voice is a privilege afforded to those for whom politics don’t bombard their personal lives against their will. 

So maybe there’s absolution for those who date people with abhorrent political views. Jess forgives Josh so many transgressions, but I forgive her for her forgiveness. Josh is funny and sweet and loves her very, very much. And there’s more to him than his politics. My favorite scene comes near the end, at a party thrown by Jess’ friends. Jess is annoyed at Josh for announcing he thinks eviction is fine. Moments later, she finds him out on the balcony, having rescued a stray kitten. Jess is both wholly charmed and deeply annoyed. She wants consistency, but Josh eludes easy labels of “good” or “bad.” 

The juxtaposition of the cruelty of his politics and the warmth of his affection for a kitten reminds us that everyone has a softness to them, everyone contains multitudes. The book is worth reading for the very reason people tried to cancel it before it came out—because it isn’t afraid to find the humane side of those we vilify, often for good reason. Everything’s Fine argues that it’s worth asking if a racist Trump voter is as worthy of love as anyone else.

Rabess’ choice of Trump as the demarcation, the point of no return, is apt, as he’s unintentionally moved the line many times. After each unspeakable transgression, he gives his old supporters a new chance at redemption; after each massive moral failing, a new crop of “Never Trump” Republicans were born. On the eve of Trump’s third nomination, is it time to ask if there’s redemption for 2016 Trump voters? Are those who voted for him in 2016, but not 2020, now dateable? Those who were with him until Charlottesville? Until the pandemic? Until he told the Proud Boys to stand back and stand by? Until January 6th? And if there is—could you be the one to give it to them?

On its face, Everything’s Fine asks us to consider where to draw the line. Zoom out slightly and the fundamental question broadens: do these lines benefit us? Does the very act of moving the line make you a hypocrite? If so, are we all hypocrites? I can’t reveal what Jess chose, but it’s a mark of Rabess’ phenomenal storytelling skills that I was left guessing until the very last page.