Both Sides of a Breakup: He Liked Donald Trump (2024)

Illustration: by the Cut

In “Both Sides of a Breakup,” the Cut talks to exes about how they got together and why they split up. Etta, 36, and Jeff, 38, started a situationship in the Hamptons that didn’t translate well to the city.

Etta: We met in the Hamptons when we were babies. It was early summer of 2016.

Jeff: We met out East the summer I turned 30.

Etta: I’d been renting the same share-house with the same girls for a few years. I worked in the city during the week and would go out to the house every weekend. We always had our routine: pregame at our place while someone grills, drink a ton, then go out. Every summer, we all had tons of hookups and relationship dramas. It was early in the summer, so we were all like, “What trouble will this year bring?”

Jeff: I had a sweet place in Amagansett with a few buddies. I’ve never been a Hamptons guy — could never afford it till now, honestly — so I was eager to get into the spirit of things.

Etta: One of my girlfriends, Rachel, doesn’t drink, so she’s always our driver. I was drinking screwdrivers all night. I remember having a sore throat and thinking the orange juice would be good for me, plus some Tito’s vodka; I know — call it “Hamptons math.” The girls I was sharing the house with wanted to go clubbing, and even though I hate clubs, I was drunk and always looking for guys, and they easily convinced me to come along.

Jeff: My buddies and I all had some luck that year workwise. I sold a TV show that I’d been writing for a few years while working in the fintech industry. My friends had gotten various promotions at their law firms and whatnot. It was a sick rental, and we felt like ballers. I grew up in Florida, so I love beach life.

Etta: Jeff’s friends were flirting with my friends. I thought Jeff was the cutest one of all. I liked his height, and he had a quiet confidence that I’m attracted to. There was something kind of preppy about him, or maybe he just seemed rich. I remember thinking he was the most promising in terms of finding a future boyfriend. I was really looking for a relationship. Dating was so tiring, and even though I was only 28, I felt ready to settle down.

Jeff: All of Etta’s friends were hot. We were like, Jackpot! I remember thinking, I’ll take any of these girls home tonight! But Etta was flirting with me the most aggressively. She told me she was a writer, and I was attracted to that because I had just sold that screenplay and my more bro-y guy friends didn’t understand my creative side. We bonded about that a little bit, but it was loud, so we mostly just drank and danced.

Etta: He introduced himself as a writer, which I thought was a plot twist. His look screamed lawyer or banker. I was a copywriter at an advertising agency, but I also freelanced for some lifestyle websites.

Jeff: We got hammered. I bought everyone a couple bottles of Champagne at our table. Etta was plastered. She was dancing on the tables, etc. She was clearly a very sexual person.

Etta: I got really drunk. I was afraid to throw up in front of him, so I just left the club, puked on the road, and found Rachel to drive me home.

Jeff: We exchanged info and then she left with some friends; I can’t remember the details.

Etta: I was so sick the next day. A hangover plus strep. Later in the day, I saw a DM from Jeff. He remembered my first and last name and found me on Instagram. I was so happy to see that he thought of me, and even though I felt like death, I was smiling from ear to ear. I didn’t text him that I was so deathly ill because it just wasn’t a sexy thing to say.

Jeff: We started bullsh*tting via text. Just basics like “Where did you grow up?” “Do you have brothers and sisters?”

Etta: Our texts were witty and cute. I was crushing on him pretty hard from the start. And then we spent the rest of the summer hanging out. We hung out the next weekend, just us, and we had sex on our first date. The sex was amazing. I honestly couldn’t get enough of it. And we became a couple quickly.

Jeff: We were hanging out all the time. I liked spending time with her. We had an incredible physical connection. She’s a very attractive girl. She always had to go back to the city for her job, which was in an office, whereas I could pretty much work from wherever since my boss gave me a few paid months off to work on the TV development of my series. I would miss her when she wasn’t at the beach.

Etta: After all of July and August together, it was clear that we were a couple. I knew we were monogamous because I asked him to be monogamous and he was in full agreement that that was the right move. And as for our official status, I mean, I fully thought we were boyfriend-girlfriend. It’s not cool to ask about labels, so I didn’t get into specifics with him, but all signs pointed to the fact that we were a couple.

Jeff: Were we sleeping with other people? No. She asked me not to sleep with other girls if we were going to be in an intimate relationship. I respected that. Were we a serious couple? Unclear. Truthfully, it was always a summer fling for me. My career was more important than anything. If my TV series took off, I’d probably have to move to L.A. If it didn’t take off, I had enough momentum to take on other projects in that world. My love life was secondary, or even third or fourth, to anything else. I was really young and hungry careerwise!

Etta: So it’s September and everyone is moving back to the city, and I’m excited to see Jeff more — and in my real life, not fantasy Hamptons life. A couple of my friends ended up dating a couple of his friends, and we had a little crew to start the fall with. I really liked Jeff. He was kind of detached emotionally and really focused on his work, but behind closed doors he was sweet and affectionate. He texted and called all the time. He called me “my girl” in front of people. I met his parents, who were visiting from Florida. They were super-nice but definitely into Donald Trump being the next president. I saw it as a small red flag but didn’t think much about it. I also believed there was no way in hell he’d get elected, so it seemed like a moot point. They also made an off-color joke about my skin color (I’m half-Filipino). But parents can be stupid. It was fine.

Jeff: Oh yeah, my parents have been Trump supporters from the start. We don’t agree on politics, but I understand where they’re coming from. They’ve worked unbelievably hard for their modest salaries, and they don’t want to give it up to lazy people … I mean, that’s how they see it, not me. I’m a liberal guy, and I would never vote for Trump, but back then I kind of admired the balls on him. I was entertained by his antics, shall we say. I was also very ill-informed. Now I recognize that he’s a sociopath.

Etta: Everything fell apart at once. Trump got elected, and I was wrecked over it. At the same time, Jeff found out that his TV series was not happening. He was freaking out. Not in a good way.

Jeff: The producer on my project wanted me to pivot and write it as a feature, not a TV series. I was psyched. Before I knew it, I was writing a movie.

Etta: It felt like Jeff was pulling away. He was never available to hang out. He blamed deadlines and other time crunches. He was totally unconcerned with the fact that Trump got elected. He said I was being annoying about the fact that I felt scared for our country.

Jeff: I’m not sure if it’s PC to use the word, but Etta was being a snowflake. She only wanted to talk about politics and the doom and gloom of our nation’s future. I wasn’t especially thrilled that Trump was elected, but I had so many other things on my mind. It was around this time that I felt the relationship had run its course. She was upset all the time about Trump and politics, and I was somewhere completely different in my headspace. I just wanted to write this movie and keep the career on track.

Etta: Whenever we’d hang out in November and December, it was all because of me. I’d chase him to make plans, I’d make the dinner reservations, or I’d show up at his house and basically just f*ck him. We were super-disconnected. I felt distraught. First our country was a dumpster fire and then my relationship was drifting away in front of my eyes. Even so, I wanted him to be my boyfriend so badly. I was dead set on it. In hindsight, I don’t even know why. He didn’t exactly fill my love cup, but I liked the optics of it — we were a striking couple with a lot of chemistry — and I guess I was also dickmatized. I was so attracted to him.

Jeff: I personally did not think hanging out for a few months warranted a proper breakup, but Etta was relentless about seeing me. I remember she showed up at my house one day after partying with her friends, and she was like, “I want to fight for us …” I was like, “There is no us.” It was pretty rude of me, but I just snapped. I was like, “We aren’t a thing.” Go back to your woke friends still crying about Hillary while their fathers pay their rent. I didn’t say that part, but I was kind of thinking it.

Etta: I went to his apartment, all messy and drunk, and begged him to prioritize our relationship. He was so cold. He told me we were never in a relationship. Totally gaslit me. Asked me never to contact him again. I left and just sobbed the entire night and for a few days after.

Jeff: I was really irritated that she kept showing up; it felt a little stalkerish. I just needed to shut it down. It took a while for her to finally go away.

Etta: It took a few months, but finally I stopped thinking about him and then I met someone about a year later. My new boyfriend is a professor of international politics, and I’ll tell you right now: He is no fan of Donald Trump — there’s no gray area around it. I look back and laugh about how desperate I was to make Jeff, a closeted Republican, my boyfriend. I was so desperate and so insecure. I’ve had a lot of therapy since then!

Jeff: I’m now married. My wife and I are both full-time screenwriters. We’ve had a tough year with the strike, and she’s trying to get pregnant and yadda yadda yadda, but I’m very happy and very much in love. When I think about the Etta situation, it just feels like we were silly and immature. Every now and then, I’ll DM her about something she’s published or vice versa, and it’s all good.I wish her only the best.

Etta: I think he’s a super-talented writer. He’s finding enormous success, and despite it all, I’m rooting for him. He was a real asshole to me when we were dating — and I tell him that straight up when we talk — but he deserves a happy ending. His wife looks perfect for him. Good for them.

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• both sides of a breakup
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