I Dated Bad Men Till a Bad Man Became President


September 1, 2017

James wore flip-flops and cargo shorts on our first and only date. I was sporting black denim and breakneck heels and everyone in the bar turned to stare as we glided across the room, two sartorially mismatched strangers romantically matched on the dating app Tinder.

His sloppy wardrobe wasn’t my first inkling of trouble. All that Friday afternoon before the date I’d felt uneasy. Not that I believed James was dangerous or anything—though his profile featured several jujitsu action shots—but somehow I knew I’d be disappointed. Intuition, maybe, or maybe it was that somewhere over the course of our handheld correspondence (and after we’d made plans to meet) James had updated his profile to include the following sentence: Not very political, I wrote in Tom Brady, better luck next time, followed by an emoji of a man shrugging.

That emoji embodied my entire romantic history. Should we go out again sometime? How does Indian food sound? Can you go down on me now? Do you see us together when we’re eighty? On the receiving end of these questions has always been a man shrugging, frozen in time like a bug in amber.

Before reinstalling Tinder and other dating apps, I made a pact to go on a date with anyone who asked, so long as they seemed decent and marginally interesting. James described himself as a former chef turned HVAC specialist, which gave me a tingle—my desire is firmly blue-collared. My ideal partner is the spiritual progeny of Bruce Springsteen: a poet lumberjack, someone who can debate books/movies/music while refurbishing the furniture we’ve rescued off the side of the road. If James could bring central air into my life—and talk at length about Steely Dan—we could have a love story for the ages.

We slid into a booth, gripping our Bud Lights. The jukebox bleated “Despacito.” Menus appeared. An afternoon of jujitsu had left James famished. Is that why you were late? I wanted to ask. Jujitsu?

Instead, I opened my purse and announced, “I got the goods you requested.”

Minutes before leaving the house to meet James, he’d texted saying that he was running anywhere from fifteen minutes to a half-hour late, and could I bring him a phone charger? I’d wanted to call the whole thing off right then, but couldn’t live with the gnawing possibility that I was letting The Love of My Life slip away over an iPhone charger.

Now here I was, forking it over, an eternal sucker. I’ve always made concessions for men because I might never have sex again if I didn’t. I’ve been accused of hating men, but, really, I love them so much that finding a suitable one to date has become my personal Vietnam.

“Oh my god, thanks,” James gushed. “It’s just, I worked all day, then had this jujitsu lesson, and my phone’s at three percent. And I’m super hungry, by the way, so I am ready to eat.”

James’s dinner arrived just in time for his life story to unspool. He was thirty-seven, never married. A few years ago, he’d helped a friend open a restaurant, where he worked as the chef making what he dubbed “slutty food”: “Just honkin’ burgers and good steaks with, like, blue cheese cream sauce. Rich, messy pub grub—but done really well.”

I nodded, unamused. Between the political apathy, equipment requests, and slutty food, James was decidedly not the man for me. But I resolved to make the most of the night anyway because life is short and there I was. So, I ordered another beer and dipped into James’s arsenal of tater tots and Philly cheesesteak-stuffed egg rolls as he blabbed on about how his friend later sold the restaurant and didn’t bother paying James the $40,000 he was apparently owed. This launched him into an emotional tailspin, he said. He moved back home. His girlfriend dumped him. He couldn’t sue his friend because they’d never formalized a contract. Now he lived with an alcoholic uncle who’d finagled him into the union.

Twenty minutes had elapsed between hugging hello and arriving at James’s fried food confessional. I felt a lecture rising inside my throat about legally protecting yourself when entering any business venture—especially with a friend—but choked it down with more tots. NO EMOTIONAL LABOR.

At one point in my life, I would’ve found James’s irresponsibility, his utter hot mess-ness, irresistible. Over the past five years I’ve dated indiscriminately, doggedly, like I’d just gotten out of jail. And, in a way, I had. I’d spent my entire twenties in a sexless relationship with a balding bartender ten years my elder, only to leave him for a scuba instructor in Mexico. I moved to another country for the latter, so when our relationship failed epically, torching my faith in love, I nosedived into a years-long spree of flings—ephemeral and mostly meaningless encounters with unfit men.

Eliminating the prospect of love excused my questionable judgment and allowed me to enjoy these men as experiences. A few highlights from my carnal merry-go-round: A daredevil phlebotomist who rode a motorcycle (usually with his longtime girlfriend); a twenty-two-year-old barista who once padlocked me in his room while he went to buy condoms (he didn’t trust his Craigslist roommates, he later told me—hence the lock); a beautiful Brazilian grad student whose twenty-minute-long stoned renditions of “Stairway to Heaven” made me wish I was dead; and an enigmatic gang member who once burned down a rival’s house and asked me for an alibi.

Things surely couldn’t get any worse with James—until they did. When I told him how my first book traced my unique relationship with my father, who died from a chronic illness when I was twenty-one, James confided that his father died from a heart attack when James was just eighteen.

“Sounds like you had a special bond with your dad, but there’s nothing like the bond between a father and son.”

“I don’t think gender has anything to do with it,” I countered. “A parent’s a parent and children are children. It’s hard for everyone.”

“But it’s that father-son bond,” James continued. “There’s just something special about it. I’ve never been the same since.”

“Losing a parent is hard—period.” Then I laughed. “Are you trying to ‘out-death’ me or something?”

“No, I’m just saying that you can’t really understand the bond between a father and son.”

“But it has nothing to do with gender. If my mother died tomorrow, I won’t tell you how you’ll never be able to comprehend it because you’re a man.”

“But I won’t—because you have that mother-daughter bond.”

“But we don’t,” I told him, my voice quavering. “You can’t just assume stuff about a stranger. And, in case it wasn’t clear, I’m kind of a rabid feminist.”

James shrunk a little in his seat. I could tell he wasn’t deliberately trying to upset me, but also that he didn’t understand what he’d done wrong.

“I can see that,” he said. “How’d that happen?”

“Life? Intelligence? Men? The election certainly didn’t help.”

James peered up from his feast and said, exactly, this: “I didn’t vote for the guy, but I don’t mind the stuff he’s doing.”

It was the verbal and moral equivalent of a shrug. What was my future with men with Trump as president? I didn’t know, but I was scared. As James launched into a tirade against Hillary Clinton, featuring phrases like “Benghazi,” “her emails,” and “the fake news media,” followed by a passionate petition for a broader Muslim ban, I felt my heart rate climb. Then, actual tears welled in my eyes.

“I think I should go,” I announced.


“Yeah, really.”

Okaaaay,” James said, his face reddening. “Do what you have to do, I guess?”

That’s when I grabbed my purse and fled. It was the first time I’d ever walked out on a date because I was used to withstanding—and even welcoming—all manners of outrageous or offensive behavior so long as no one got physically hurt. A year ago, I would have stayed in that bar. A year ago, I would have given this bad man a chance, but this was 2017, and I was fucking done.


March 1, 2016

On Super Tuesday of 2016 Adam liked me on Tinder. That morning, I’d cast my primary ballot for Hillary Clinton and that evening, messaging on the app, Adam said that working late had kept him from the polls. I chided him lightly, then let it go. Adam had a steady job with a successful start-up, spoke in complete sentences, and we shared an unflinching appreciation for the Guns N’ Roses catalog. I said yes when he asked me out that Friday.

We met after work in a bar and ka-pow! Insta-chemistry. With his bald head, blonde beard, and sleeve of tattoos, Adam was a dead-ringer for the Red Sox’s Mike Napoli, a fact I knew because at least two people interrupted us for autographs.

I wasn’t necessarily looking for love, but I was starting to tire and suspecting that I’d reached the finale of my half-decade of sex and protracted romances with ne’er-do-wells and criminals. And Adam seemed genuinely nice, which scared me. I’d intentionally avoided men who seemed nice, responsible, and mature because I didn’t want to get hurt again. I’d loved the bartender until he gave up on life. I thought I’d marry the scuba instructor until he turned possessive and paranoid. All this left me wounded and distrustful of men. And the election only magnified my doubts and fears because one of the presidential candidates not only represented the absolute worst in humanity, but also the basest qualities in men.

At the end of the day, I’m an idealist, a romantic, so disillusionment in dating is inevitable and expected. Yet I was still shocked when Adam announced his support for Trump at the bar. I scanned the room to see who might’ve heard, then slurped the remainder of my vodka-soda and signaled for another.

“You’re… not joking?”

“He’s the only one who can turn this country around,” thundered Adam, one-hundred percent serious.

Moments earlier, I was daydreaming about making out in the restaurant’s restroom. I was feeling Adam. Now that he’d proclaimed the last thing I’d ever wanted or expected to hear, I was flummoxed—but intrigued.

Up until that moment, I’d never met a real-life Trump supporter. Clearly they existed, but not in my liberal Boston bubble, anyway. Or so I’d thought.

Adam believed all lives mattered and favored total annihilation of the Middle East—problem solved. He’d voted for Obama—“twice,” he claimed—but was earnestly worried about terrorism and ISIS. It kept him up at night, he told me. He’d lived a block from the Boston Marathon bombings and, after that day, he was fundamentally changed.

We fought for hours at that bar, drunkenly raving, alarming strangers and bartenders alike. Adam’s unflinching Trumpism and deep psychological fear of death by terrorist was so bizarre that it bordered on the familiar. Being with fucked-up men was both my comfort zone and defense mechanism. I needed to deeply despise a man to feel comfortable around him, because he became disposable and I became powerful. Ours was an ideological war and Adam was sexual gunpowder.

“We could argue about this until the end of time,” I finally sighed. “Let’s talk about something else.”



“I just saw Billy Joel in concert.”

“Of course you did.”

“What’s wrong with Billy Joel?”

“Nothing’s wrong with Billy Joel. He’s just a maudlin wanker,” I said. “I do love ‘We Didn’t Start the Fire,’ though.”

“That’s my least favorite Billy Joel song.”

“Why am I not surprised?”

“Let’s make a bet then,” said Adam. “Let’s go back to my place and we’ll listen to ‘We Didn’t Start the Fire.’ I have an epic sound system. We’ll play it, and if I know more lyrics than you, you have to kiss me.”

I smirked. “And if I know more lyrics than you,” I said, then paused, “you have to vote for Hillary.”

We walked through the drizzle back to Adam’s Back Bay apartment. He paid an exorbitant amount to live in a windowless, cramped one-bedroom in the heart of the city. But at least his place was organized. This was a man’s house, with a huge TV, stereo, the obligatory George Foreman grill. Adam poured us another round of vodka-sodas, then queued up the song.

Adam and I stood facing each other as the opening bars of the song crackled through the speakers, then we launched our sing-off: Birth control, Ho Chi Minh, Richard Nixon back again. Moonshot, Woodstock, Watergate, punk rock—

“We Didn’t Start the Fire” has always reminded me of the Gulf War, which broke out when I was eight years old, in 1990, a scant year after Joel’s song hit the airwaves and MTV. I remember watching the nightly news with my parents and seeing the combat footage aired, wincing and flinching with each dusty desert explosion. I didn’t understand every historical reference in Joel’s song and music video, but even as a kid I understood its message—that humans have been doing terrible things to each other since the dawn of time, and that we still haven’t found a way to be better to each other and possibly never will.

When it was over, it was clear Adam had won the duel. Even tipsy, he’d hammered home every syllable.

So I kissed him, which led to staggering down the hallway, which led to epic hate-sex on Adam’s four-poster king, the size of his tiny bedroom. When it was over, it was only 9 p.m., the witching hour for Friday night Dateline, a show I watch begrudgingly because almost every episode is about a woman’s death, usually at the hands of her crazed husband or jealous lover.

Adam ordered a pizza. I would never love him, I knew, but he was already reading my mind when it came to carbohydrates. As we ate, spooled in blankets on his micro-suede sofa, I noticed he’d drank an entire bottle of vodka.

“That was full a while earlier,” I said.

Adam didn’t even look up. “I have a problem,” he said, flatly. “I drink every day and I don’t think I can stop.”

Maybe it sounds selfish, but I just wanted to sit in my post-sex haze and eat pizza and watch trash TV. Adam’s Trump affinity might’ve been a novelty to me, but his alcoholism wasn’t. I wanted to leave right then, but stayed a little while longer for fear of being too abrupt, because what women must also worry about is suffering repercussions for rejecting a man. Dating comes with its own set of risks, not the least of which is men tricking you into believing they’re something they’re not.

“Don’t,” he pleaded. “You felt how nice my bed is—just stay. I’ll make breakfast in the morning—anything you want. Just don’t go.”

But I did. I had to. I found Adam’s fear, his utter desperation, alarming. Maybe I knew it too well. As much as I feared being heartbroken again, I was doubly afraid of being alone, so much so that I forged a symbiotic relationship with the awful men I dated. We feasted off each other’s dysfunction—they wanted sex, to test the boundaries of their narcissism by being with someone who accepted the lowest common denominator of their behavior, while I felt a deep, pathological need to be seen—as smart and distinguished, fucked-up but a diamond nevertheless. Deep down, I wanted to be the thing that might turn them, from bastard to redeemed.

I’ve thought a lot about that night, about leaving Adam alone in the din of that windowless apartment. I remember feeling bad that I didn’t stay, and feeling guilty that I escaped. But if the roles were reversed—if I’d outed my problems to a man I knew for a few hours, then begged him not to go—Adam would’ve wasted no time in fleeing.

We never saw each other again. But I still thought about Adam, especially after the election, and wondered how elated he was to know his man won. One dark November night, just as I was slowly emerging from my foggy fugue of depression, I clicked to his Facebook page—just to spy, just to see if he’d posted some gloating dispatch—but found memorial messages instead. Miss you, bud, one stranger wrote. Work will never be the same again.

I quickly Googled his name and an obituary popped right up. Adam had died “unexpectedly in his home” almost a month to the day since our one-night rendezvous. I could still see him at the door, forking over cash to the Domino’s man. Handing me a paper towel to wipe the grease off my chin. The empty bottle of vodka on the table. The unmade bed. His face as he begged me not to go. My Uber ride home. He never saw Trump win.


July 24, 2017

“I was just there,” I announced to the man at the bar.

He was burly and bearded and reading a thousand-page tome on economics. His shirt read Dangerous Man Brewing.

I’d recently returned to Boston after a trip to Minneapolis to visit my best friend who’d accepted a bigwig job with corporate Target and moved into an apartment building with a gym in the basement. Over the course of a week, we shopped and ate and karaoke-ed; we went to Paisley Park and wept when our tour guide pointed out Prince’s ashes, placed high on a shelf overlooking the building’s sunny vestibule. We had also visited Dangerous Man Brewing, where we sat drinking sour beers and reminiscing about our childhoods in North Carolina. On our way out, I’d perused the brewery’s t-shirts for sale and wondered about that name and the men who’d wear it across their chests so brazenly. Were they being ironic because they were the opposite of dangerous? Or was it way less complicated—just a pure love of this brewery and its beer, the way we wear band t-shirts? Or was it a straight-up advertisement, as in, I am fucking batshit?

“Huh?” the bearded stranger said.

“Your shirt,” I said, pointing. “I was just there. In Minneapolis. Is that where you’re from?”

He wasn’t and the shirt was a gift, it turns out. I considered whether the shirt might’ve been a warning to me—some message from the cosmos, a signal to run. As much as I believe in symbols, I’m the first to dismiss them as nonsense when they don’t suit my romantic agenda.

We made introductions, I flirted with David some more. He asked for my number, then he was in the back of my girlfriend Susan’s car, bound for a comedy show where Susan’s friend was doing stand-up. It was Monday and chilly for July; the rain was slanted and sharp. On the radio, NPR commentators discussed Trump’s outlandish stump speech to a gathering of Boy Scouts in West Virginia.

“Even I think he went too far,” chimed David.

Susan and I looked at each other.

“Oh my god,” I wailed. Was this happening again? How could this be happening again? “Please don’t tell me you voted for him.”

“Of course I did,” spat David. “I’m reading a giant book on economics. Trump’s a businessman—he gets it. Sure, he’s insane, but that’s because he’s not a career politician and it’s great. Everyone’s freaking out and I love it.”

“People are legitimately scared,” Susan said. “How’s that great?”

“Because people got used to Obama, who was pathetic,” he replied. “Look at China. Or North Korea. How do you think we got here with them? Obama.”

“Yeah, and now your orange guru going to get us all blown up. Thanks, Obama,” I huffed. “Do you really not see that he’s psychotic?”

Jeez. If you want to just pull over and let me out on the side of the road, I understand.”

“Oh, shut the fuck up,” Susan growled. “No one’s getting out of the car.”

“We’re gonna drive this car straight off a cliff,” I said, joking, but also not joking.

Thelma & Louise,” said David.

Thelma & Louise is the greatest movie ever made,” said Susan. “Two women who can’t take men anymore and take fate into their own hands.”

“I hate that they had to die, though. Is death really the only way to escape men and their bullshit?” I asked. “I really want to believe that’s not true.”

That was the idealist in me talking. Truthfully, I wasn’t sure the movie was wrong. How many years have been shaved off women’s lives trying to convince a man to act decently? Geena Davis and Susan Sarandon were fucking done. I get it—and that scared me.

Minutes into the comedy show, David disappeared completely. “Good,” Susan said, when I told her. Then she gripped my arm and looked at me square and said, “I hate him, Sarah.”

My phone dinged seconds later. Thanks for the invite, but I think I should go, David’s text read. My presence might kill your friend’s ability to laugh. And if you weren’t attracted to me, you’d feel the same way.

He was right, of course. I tolerated David because I was attracted to him, and I was attracted to him because, like all the others, I hated him in some dark, primal way.

That’s some bullshit, I typed back. You’re bailing?

Fine. I’ll stay, David quickly replied. See you in a minute.

I almost felt badly for David. It was clear he wanted us to accept him, Trumpism and all. But it was somehow easier to forgive Adam for loving Trump because the election hadn’t happened yet; we were still swimming through some apocalyptic fever dream I never imagined would become reality. Like millions of other people, I trusted that Hillary Clinton would triumph and override these petulant man-children screaming for attention in the sandbox of civilization.

But during the election, and especially during the debates, watching Trump endlessly insult and humiliate a woman—even stalking and menacing her on a national stage—was like viewing my own life played back to me, and the lives of my girlfriends, and the lives of countless women. In so many ways, the election forced me to grow up, to stop making concessions for men, to not turn away from misogyny. Yes, with David I’d saved the weirdest and worst for last. One more hate-fuck for the road, you know?

David slept over that night and the sex was amazing. Sex is always amazing with a rogue because there’s a sense that nothing’s at stake for anyone, ever. But ushering him out of my front door just shy of 8 a.m., wincing as he pecked me goodbye, I knew my extravaganza was finally over.

If I’d loved anything about those men, it was sunbathing in the heat of our dysfunction, feeling gravity-less, for once, because alongside them I could forget the other men who’d wrecked my heart. Their dishonesty and danger was easier to look past then. The world had not yet shifted. But then it did, and I woke up.


Rumpus original art by Stephanie Tartick.

Sarah Sweeney's essay collection, Tell Me If You're Lying, was released December 2016 by Barrelhouse Books. She has also written about catfishing musicians on AOL in the 1990s for Salon and a personal essay about falling in love with a son of a preacher man for Catapult. She works as a writer in Boston. More from this author →