Both Sides of a Breakup: She Hooked Up With a Woman She Met at Work

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. Anna, 35, and Cass, 36, met while working on a booze cruise on the Hudson River. But when Anna got a job as a private chef, her life went in a different direction.

Anna: I met Cass when we were both catering on a booze-cruise “yacht” on the Hudson River. We were both newly out of college, or in my case, culinary school. It was a strange job … half the staffers were on drugs, the rest were kind of insane. And the clients were always such douchebags. But I was working in the kitchen, so it felt like a real, grown-up cooking job, and I liked that.

Cass: I remember meeting Anna and thinking that she was too classy for this job. We were cleaning up diarrhea-stained toilet bowls. There was one banker who vomited all over the inside of the boat, and it was our job to wipe it up. I’m from a bunch of hicks in upstate New York, I can handle it. But Anna was so pretty and delicate, all “Connecticut,” and it seemed like she should have been a charter guest, not a glorified maid.

Anna: We became really good friends that summer, grinding it out on this gross boat — making really good tips, I should add.

Cass: She slayed at that job; I mean, that’s who she is. She’s amazing at everything.

Anna: We start hanging out after shifts. I was extremely sexually repressed back then, but I didn’t talk about it. Not to anyone. I never even mentioned it to my therapist. This was 2014, and while it was hardly the dark ages, I didn’t have the language to express my feelings. It was like, I definitely wanted to get married and have kids, but I also had no interest in dick. I was on a softball team in high school and undergrad (I went to a liberal arts college before culinary school). I always loved the company of lesbians, but I fully identified as straight.

Cass: Our first kiss was pretty magical. We finished a particularly hard shift, the summer was ending, and we had stolen a bottle of Champagne and some cheese, grapes, chocolate, and romantic accoutrements from the kitchen. We made a midnight picnic right there on the waterfront … and I finally kissed her. We’d been friends for two months, and my feelings were really strong. I was dating a few other girls at the time, but my heart really belonged to Anna. She was sort of untouchable, in my mind, so after she let me kiss her — and we had a whole night of making out — I felt like maybe she could actually be my girlfriend.

Anna: I was smitten by Cass. For one, he’s really hot. He’s got that classic sexy bad-boy look, and he’s also supersweet. He’s wholesome in a way you don’t find in New York. The “I’m still not sure what to do with my life” thing was hard for me to wrap my head around, and a bit of a red flag … a light-pink flag. I was just so motivated at that point. I could see my whole future, professionally, and how it would play out. I put all those plans into motion that fall. I got a cooking job with a chef I really admired — female, lesbian — and devoted myself to work. Cass became my official boyfriend right after that night of making out.

Cass: I remember at the end of the night saying, “Will you be my girlfriend?” And she said “yes.” It was very sweet and simple.

Anna: I was juggling this new job and new relationship, but it was actually very nice. Cass was so supportive of me, and I can’t lie, I loved showing him off at work. He’s magnetic.

Cass: I was content just rooting for my girl. For my work, I took on freelance graphic-design projects; I kept catering on that fuckin’ nasty booze cruise; I painted apartments as a Taskrabbit. I was hustling. My dream was to work in sports. I wanted to be a physical therapist for professional athletes, but I couldn’t break in. I had a degree in PT, but the jobs I was being offered were not good. I remember Anna told me I should become a FedEx delivery guy, which is what my brothers do, and for some reason that really stung me. I guess I was insecure, especially as she rode the escalator up toward serious success.

Anna: Okay, the sex. I was never into it. That has nothing to do with Cass. Penetrative sex never has felt good to me. I was a good faker. But it wasn’t an issue: I was always just focused on my career, and sex felt like an afterthought.

I do remember, more than once, suggesting he get a friend with benefits who he could have tons of sex with while I was at work. I really would not have cared if he got all that energy out with someone else, and then we could just have our happy, loving, nonsexual relationship. I think he considered it. Looking back, it could have maybe saved us if I knew more about ENM then.

Cass: The sex was great, but she was always tired after long shifts at the restaurant. So, yeah, maybe I was frustrated in that way. I’ve never cheated on a woman, and the thought never crossed my mind. She would not have been cool if I strayed. No. It wasn’t on the table.

Anna: After about a year of dating and simultaneously a year working at that top restaurant, I was approached to become a private chef for a very wealthy family. The money was bananas. But it also meant a lot of travel to all their homes — the Hamptons, L.A., etc. Cass was, as always, supportive. We were living together by then, in a studio in the West Village, which he decorated and cleaned and made so cute. I was never home because of my work schedule. Again, I told him he could outsource the sex, since I’d never be around. He was always horny, and so adorable, and he deserved to be loved and fucked more often.

Cass: I don’t remember any suggestion of me having sex with other women. I don’t think I ever could have done that. I wasn’t raised that way.

Anna: As I traveled with this family, something changed inside me, and I started to feel … sexy, I guess. I changed my hair and lost weight. People would hit on me when I was cooking for dinner parties — both men and women — but it happened a lot with women. Like, rich men’s wives. One rich wife came into the kitchen once and asked me if I wanted to hang out with her in the bathroom. I couldn’t leave my station, but I was really turned on by that. I started paying attention to those advances.

Cass: While she was away with that family, I worked on our apartment. I was installing a chef’s kitchen for her — it was a rental, so kind of a waste of time, but I had nothing better to do. I covered our ugly countertops with butcher block and found the right-size Viking stove, for cheap, on Craigslist. I painted, cleared all the clutter, that kind of thing. It was one of the most exciting moments of my life, because I knew she’d love it.

I also went back to school for sports medicine — Anna inspired me to enroll. I was pushing myself, for her, but it should have been for me. I think I was also sort of depressed. I was feeling left out. Like, why wasn’t she ever inviting me to the Hamptons and shit? Was she hiding me?

Anna: At some point, I took someone up on it. It was a big party out East. I was cooking. And after my work was done, a single woman, who was openly gay, took me out to a bar in Montauk for a drink and we hooked up at her place. It was pretty life-changing. I had the biggest crush on her and, more important, it made me never want to go back to Cass. I just couldn’t. I had cheated on him. I had finally unlocked my sexuality, or begun to. I was thriving, and going back to him felt like a very backward move. The problem was, I loved him, and it made me sick thinking about hurting him.

Cass: I was losing her, I knew it. I was hearing from her less. No more daily check-ins. We had no plans for Christmas, which was coming up. The last two Christmases we had gone to see my family or her family, and she couldn’t commit to anything because of her work schedule. I was feeling so fucking lonely. But one cool thing is, through her fancy bosses, I got an internship at MSG. I felt old to have an internship — I was 28 or so — but it was a big win.

Anna: Cass had plans to see his family upstate for Christmas.

Cass: I had no plans. I was dreading the holidays in the West Village without Anna, without anyone. Finally, I called her — she was in the Caribbean or something — and I was like, “Babe. What is going on with us? Are you ever coming home?” And she dumped me.

Anna: It didn’t happen right away … it was a series of calls, and meeting up at our apartment, and a couple make-ups and breakups. It was very hard to cut the cord.

Cass: She just dumped me on that call. My heart broke, but a small part of me also felt relieved.  Not at that moment. At that moment, I just cried.

Anna: It took a lot of strength to end things, but I was now seeing that woman from the make-out out East, and she was disgusted that I was essentially cheating on someone. She was right. But that doesn’t mean it was easy. He was an incredible boyfriend.

Cass: So I spent Christmas alone.

Anna: I spent Christmas working in St. Barts.

Cass: Moving out of our apartment was awful. I felt like such a loser. Anna wasn’t really in town ever. I wanted to see her, but in hindsight it was better that I didn’t.

Anna: I would come in for a day or two every few weeks, but I was too wimpy to cross paths with Cass. When I came back, I asked him to stay at a friend’s. I remember him agreeing that it was a good idea. I wasn’t sure if I could ever look at him again. I hated myself for hurting him.

Cass: I didn’t hate her. She had vaguely hinted that she might be gay and had to explore that. I wasn’t totally surprised. And, yes, it was slightly less painful that she hadn’t found another man. Within the next few weeks, I moved in with another single guy I became friends with at work. And we turned into two single and mingling fuckboys. It wasn’t the worst thing. I did not mind all the sex; I’m not going to lie. It lasted like four years, if I’m being honest.

Anna: So, three or four girlfriends later, some more toxic than others, I am in a serious relationship with someone I think will be my forever love. They are also in the food industry. They also travel all the time. It’s a very healthy, happy situation for me.

Cass: Now I’m engaged! My girl is actually pregnant. I’m a very happy man.

Anna: We follow each other on social media, and I’m so happy every time I see a picture of him and his girlfriend. She seems very nice and pretty.

Cass: Do I cringe a bit when I see pictures of Anna with her new partner? Maybe. It’s harder for me to see her in all these fancy places. I’ll always blame her job, and the people she surrounded herself with, for tearing us apart. Intellectually, I know it was about her sexuality, but I’ll also just feel bad that I couldn’t keep up in some way. Maybe I’m just an insecure person. My fiancée doesn’t really know that side of me. Anna brought it out of me.

Anna: The version of me who dated Cass, I barely recognize her. He was the last man I’ll ever sleep with, I can promise you that. That whole relationship feels like a sweet little movie from a long time ago. A very dated movie where everyone is straight and life was simple. But it has almost nothing to do with my reality now.

Both Sides of a Breakup: She Made Out With Someone From Work