In “Both Sides of a Breakup,” the Cut talks to exes about how they got together and why they split up. Thom, 30, and Cassandra, 32, had a friends-with-benefits arrangement that ended after Thom secretly started seeing an ex.
Thom: Cassandra and I met at a party at my house. She showed up in a yellow raincoat. She had really big curls — beautiful hair. My place was tiny, and some friends and I were sitting out on the back porch. She was like, “I’m not drinking tonight because I’m going through a breakup. It’s better for my mental health if I don’t.” I thought that was so mature.
Cassandra: Thom lived in this very old rowhouse, and the wooden slats of the porch were totally rotted through. Thom was more reserved, but we got to spend a little one-on-one time together. I don’t remember what we talked about, but I thought they were easygoing and warm. I’d just gotten out of a long-term relationship — it was a green-card marriage, but I was in love.
Thom: We went out dancing with some friends, then we went back to her place. It was by the children’s hospital, and every time a siren went off, her dog would start howling. He was this adorable schnauzer. I thought it was funny, his howl was so dramatic, but Cassandra was really embarrassed. She’d try to hold him to get him to stop, but he would only go harder. It was a sweet night together.
Cassandra: The next day was 4/20, so a friend and I got high and went on a walk. We stopped at Thom’s house, and we all went to a concert down by the wharf. There was this drag queen sprinkling condoms out to the audience. Then we went out dancing at a gay bar.
Thom: One of us said something that made it clear we had been together the night before. The other friend was like, “Wait, what?” I got flustered and went to the bathroom. Cassandra told this person everything while I was gone, and they were surprised we’d hid our sexual chemistry so well.
Cassandra: We had the sort of friend group where, every Sunday, friends would host to brew beer or do pickling and then we’d eat dinner together and watch TV. When The Ultimatum: Queer Love came out, we had a bracket written on a wall. Thom and I got into the habit of hanging out in groups until we left together. It was unspoken. We’d just look at each other, and I’d be like, Guess we’re doing this. They were dating another person in our friend group, and that felt a little more serious than what we had.
Thom: I had strong feelings for that person, who is now my spouse, and it was more playful with Cassandra. Eventually, I didn’t trust myself to be able to have a gray-area friendship with Cassandra. She and I talked about it. It was clear we cared for each other, and we thought it might be more straightforward to be friends.
But … there was a lot of push and pull. When COVID hit, my partner broke up with me. Everything was so scary, and I needed more, and they were like, “Everything’s so scary, I need less.” I was heartbroken. I was still seeing them — we’d have coffee, and we’d still hook up every now and then. We were in the same pod. After a few months, I was like, This is not sustainable; I need to interact with people who are not my ex.
Cassandra and I started talking about podding together. We’re both very physical, and suddenly we weren’t getting any physical contact. Naturally, after we podded, we started hooking up again. It was sweet but messy. I did not want to be broken up with, so I was sad when Cassandra and I got together, and the world was awful.
Cassandra: It got more serious. I felt like I really needed this thing with Thom. Everyone I lived with had their romantic partner, and we needed that too. At that point, neither one of us was seeing anyone else. We’d agreed not to see anyone.
Thom: It was great in a lot of ways and hard and stressful in others. Cassandra was seeking intimacy and comfort, and I was avoidant. Throughout my 20s, I had a drinking problem that peaked in 2020. I’d get drunk and cancel plans with her even though nothing was going on. It wasn’t that I didn’t want to be with her; I felt inconsistent and guilty because I was prioritizing getting drunk. One time, I was really drunk and planning to bike home. Cassandra told me to wear a helmet. I got defensive, like, “You can’t tell me what to do” — not the type of way I want to talk to anyone, especially a friend. The next day, she called me out, straightforwardly said I was being a dick. It was the first time anyone had been so honest with me.
Cassandra: Things devolved quickly because Thom got back together with their ex. They were lying to me about it; they’d been seeing them while we were together, even though we agreed to not do that. Their ex was also one of my very good friends, which made things complicated. I didn’t blame them for getting back together — they were always so great together — but I was hurt and heartbroken about the lying. I remember sitting on my back porch crying, feeling so devastated.
Thom: My now-spouse had always been a little noncommittal around another long-term ex and me, and this time, I needed them to be proud of our relationship and own it and for me to do that too. Cassandra and I took some space. We would hang out in our backyards sometimes, but it wasn’t the same.
Cassandra: Our relationship drifted apart. A big factor in rebuilding the friendship was their getting sober. I didn’t quite realize the extent to which their alcoholism was impacting their life. They reached out to me, probably over a year after we ended things, and asked if they could make amends.
Thom: In 2021, I was able to apologize to Cassandra for the night with the bike helmet, for not being a better friend to her, and for being a bad communicator. She had also asked me not to drink around her, and though I respected that for a couple of months, I eventually broke that promise as well, so I apologized for that.
Cassandra: That made me feel like we could start rebuilding trust.
Thom: We started meeting for coffee. We’d walk her dog and have picnics in parks around the city. There was a lot of cooking: pickled magnolia flowers, ramp lasagna, gochujang-caramel cookies.
Cassandra: We had to get back into the habit of being open with each other. I had been dating someone, and I started talking to Thom about how it was going. I could process my feelings with them, and I felt understood.
Thom: The other turning point was October 2023. We became protest buddies through pro-Palestine organizing. We got arrested together for the first time. We went to an action at a congressperson’s office, and the police told us we’d get arrested if we didn’t go back inside from a rotunda. Cassandra and I looked at each other and just nodded, and we were handcuffed.
Cassandra: Thom was like, “I’m going to get arrested — you don’t have to.” But if they were doing it, I wanted to be there with them.
Thom: Our friendship has felt really natural. There’s a lot of trust and a lot of laughter. I can just show up at her house and vice versa. She’s also good friends with my spouse. Not as close as Cassandra and I are, but they have their own thing. There was a brief period when we were thinking about maybe having a threesome, but that never happened. Cassandra’s doing the flowers for our wedding.
Cassandra: I’ve seen the ways they’ve grown. Sometimes, I’ll share my insecurities or what my worm brain is telling me, and they’ll be like, “I really relate to that.” It’s nice to have a friend that can act as a mirror.
Thom: I’ve been sober now for four-plus years, and the longer I’ve been sober, the more I’ve learned I can absolutely be a good friend to Cassandra. I was talking about her with my therapist yesterday, naming her as one of the few people I can really be vulnerable with. She allows friends to go through their journeys. She’s not gonna write you off just because you do something bad one time.
Cassandra: Last summer, I went on a road trip with Thom after a friend’s wedding because their partner couldn’t go. I got to meet their family and their siblings, and their mom was like, “So is Cassandra your third?” There’s a level of closeness and intimacy that, from an outside eye, or maybe from a straight eye, people assume is romantic involvement. There’s a touch and ease that is really common in queer friendships.
Thom: Cassandra feels more like family.
Cassandra: I don’t overthink who I am around them, ever. I love them so much. I envision being an old person with them. If I don’t have dinner plans, I’ll call Thom and their partner and be like, “What are you guys doing for dinner? Can I come over?” I’m grateful for queerness allowing me to have relationships that transform.
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