In “Both Sides of a Breakup,” the Cut talks to exes about how they got together and why they split up. Years ago, Serena, now 40, and Omar, now 55, had a sexually charged affair that turned into a relationship, even though Omar was technically already in one.
Serena: The first time I saw Omar, it was at a screening for one of his films. I was a guest of a guest. He’s in the movie business, but I’d rather not say the exact role. Let’s just say he has a powerful job behind the camera. Anyway, we made eye contact when he was walking the red carpet and I had a feeling in my bones that I’d be dating him — or at least sleeping with him — soon.
Omar: It was a chaotic work night for me, but I do remember meeting Serena briefly and exchanging business cards at the end of the night. It’s strange to say that out loud because I don’t think I’ve had business cards since, well, this was about 15 years ago.
Serena: I was totally attracted to him. Like, I went home and thought about him in the privacy of my own bedroom, if you know what I mean. I was just drawn to him. It was spiritual and existential and pretty profound. It was bigger than me. I’ve always had intense crushes … like, I see someone and need to be with them, but this one was transcendent. I emailed him later that night. It was flirty and to the point — I think I just asked him out! I had nothing to lose! At this point, I was 25 and he was around 40.
Omar: I think I reached out to her first? She worked for a company I was interested in knowing more about. I had a girlfriend at the time, who was not at the premiere, and who I was essentially estranged from, but … technically I was not “looking” or “on the market.” So I wasn’t thinking about Serena romantically when we started chatting.
Serena: Yeah, I definitely reached out first, asking him to meet me for a drink. He wrote back immediately: When and where? He knew it was a date. It was never about my work. I worked for a nonprofit in the arts. He never cared about my work. We met at a speakeasy in Soho. It’s closed now. I arranged all of it. I just needed to have him. Like, I NEEDED TO HAVE HIM.
Omar: I can’t remember the details, honestly. I think we had a work meeting. I remember she chose a spot that was rather romantic and I sort of raised an eyebrow at that. Clearly I didn’t mind too much, as I showed up without any objection.
Serena: I had a martini before he even arrived, and if I’m being honest, I also had a small line of cocaine, only because my roommate happened to have some and offered me some as I walked out the door. So I was feeling real good when Omar walked into that bar.
Omar: She was flirting. And my goodness, Serena is a beautiful woman. She looks like a movie star. And I am not a conventionally attractive man. I recognized how lucky I was at this moment … I still recognize how lucky I was.
Serena: To me, he was the most fuckable man alive. I don’t care what anyone else says. Sexiest man alive.
At some point in the evening, he told me he was in a complicated relationship that was at the end of its shelf life. I didn’t love the information, but it wasn’t a deal-breaker. I wasn’t too swayed by it. He clearly wasn’t into her. And I wasn’t trying to marry the man. Maybe it was slightly annoying that there was a girlfriend involved, but I don’t know … I had tunnel vision.
Omar: I had been in the world’s most layered and complex relationship with a woman for about ten years at that point. We had not been intimate in at least two years. She had a very demanding job in finance, and was a complete workaholic. We were sleeping in different rooms. She never wanted to get married. She didn’t want kids. She didn’t believe in monogamy, even though we hadn’t discussed being ethically nonmonogamous or even what she meant by that blanket statement. We were two ships passing. Yes, I was a prick who was consumed by my work and my own life, but she was too. And, I don’t know, she was perhaps in denial about us. We both were. It was over. We were over. It’s just that no one was doing anything about it. So, was I single? No. Was I in a relationship? Not exactly.
Serena: We ended up making out on the street that night, and it was just as passionate as you can imagine. It was so good. He tasted so good. I would have fucked him right there on the street. But he put me in a taxi and kind of shooed me off. I was in physical pain leaving him.
Omar: We did indeed kiss that night. Serena was the first woman outside of my relationship who I’d kissed in over a decade. It was something else, I cannot lie. It was a great New York City kiss. But I assumed this was a one-night thing. We both went back to our own lives after that.
Serena: That was our pattern for the next year. Every few nights, we’d meet somewhere underground, literally, for a drink or two, and then fool around. Quickly it turned into sex, which was unbelievably good. The best sex I’ve ever had. Never at his place. But I never cared about that. It was all about animal instinct. Not about long-term planning.
Omar: I suppose we saw each other once a month after that? Maybe more. I was so caught up with my work. And my relationship at home was dead. We never spoke. We ate separately. We watched TV in our own rooms. We were just avoiding the official breakup. We are both quite repressed people, me and the girlfriend. I think we would have rather just ended things over a quick text and gone our separate ways, but we were too passive to even do that. Things with Serena were fun, energizing, never too serious. We were in some kind of relationship, but we never defined it.
Serena: We were boyfriend and girlfriend, even though I don’t think we ever do the labeling thing. I was his person and he was my person. No question. And after a year of this level of closeness, plus all the sex, I realized that I’d caught genuine feelings. And it’s starting to seriously bug me that he has a girlfriend even though he swears she’s just a roommate. And I believe him on this, by the way. I know she was just a roommate for all intents and purposes.
Omar: I’m going to sound like a cheater. I can’t emphasize enough how over this relationship was when I was seeing Serena. I didn’t even hide that I was going out to see her. I never covered it up. On the rare occasion my girlfriend was home, I’d say, I’m having drinks with a woman named Serena, she works for this foundation, etc. She never asked questions and I never gave details.
Serena: So I tell him I want more. I want to meet his family and vice versa. I tell him I’m falling in love with him.
Omar: I was in love with Serena, yes. But I was in love with myself more. Much more. That’s the honest truth.
Serena: Things start to get messy. I wanted to be “normal” together. And … I was, like, obsessed with him. The sex really made me crazy because it was so good and all I could think about.
Omar: It all became too much. I am a man with a pea brain, mind you. I got overwhelmed. She wanted me to move out, but the idea of leaving my apartment, which I loved, and changing up my routines … I’m a very routine-oriented person … I am a Virgo. It just felt like too much.
Serena: At this point, we’d been seeing each other for about a year and a half. I had a work trip to Europe planned and Omar said he was going to come. My job was paying for the hotel, so I chose a really sexy one. I was so excited to have hotel sex with him for a long weekend and eat well and just be a normal couple. Omar seemed excited. Nothing felt iffy or tentative to me.
Omar: The night before the trip, I had a bit of a breakdown. I couldn’t give Serena everything she wanted. I started feeling immense guilt for the woman I was living with. It all felt wrong and corrupt and like … the road was coming to a dangerous halt. I needed to clean the slate. I needed to cleanse myself. It was a rock-bottom few days emotionally, especially because Serena was texting me all the time wondering if I was packed, and how we were getting to the airport, details like that, etc. So I just stopped all communication. I ignored her. I retreated. I hid.
Serena: He totally fucking ghosted me. I didn’t hear from him all day before the trip or the day of. I flew by myself. I checked into the hotel by myself. I felt physically ill. I felt stupid. I felt heartbroken.
Omar: After, like, 100 texts from her, I wrote her a long one. It was a novel. I remember thinking, Will I regret this? Is she going to destroy me if I put this in writing? And then I realized, if she did, it was a punishment I deserved. I was also simply too scared to call her. But the short of it is, I ended things. I told her it was just too much and things had gone too far and basically that I was a terrible man … and I’m sorry, but I can’t do this.
Serena: The text from him hurt, but I did appreciate it. It helped my brain from going even crazier. He was the most transparent he’d ever been with me. You can’t hate a person for telling you the truth. I did not have a good trip, but I did feel better after I got his text. And I started to process that our affair was really over. It would take me months to really accept this, but I started to turn the corner after getting his text. I knew he was done with us, and in a very bad headspace.
Omar: I think we went a year, maybe years, without speaking after that. She never responded to my text, which was a bit surprising.
Serena: I am almost positive he wrote the text in a way that implied, “Please don’t respond.”
Omar: Shortly after, I moved out and my ex and I officially ended things. Our relationship had decayed so severely it was not emotional at all, other than I loved that apartment and hated leaving it. I retreated deeply into my work. I thought about Serena occasionally but knew better than to open the gates again. I was not proud of how I handled any of it, and did not want to stare myself in the face, I suppose.
Serena: I thought about him all the time. Mostly the sex. But the hotness of the affair as a whole. It was like a fantasy. Like a movie. But I knew I had to look forward, not back. I never hated him or felt angry with him. I knew the score all along. I knew what I was signing up for with him.
Omar: I’ve seen Serena once or twice in the last decade or so since we ended. At restaurants, once on the street. It’s always nice. I have a tremendous amount of respect for her. As for my love life, I am more or less celibate. I am living the monk’s life. I just work and focus on my craft.
Serena: Oh, I’m happily married with kids now. I look back on the Omar affair with fondness, actually. It’s like a crazy thing I did when I was in my 20s. It’s such a New York story. I’m still insanely attracted to him, too. I’ve bumped into him a few times at restaurant openings and stuff, and my heart — and body — just flips out. Don’t tell my husband! I’d never, ever act on it.