Lifestyle
Ode to a Gen-Z Situationship
I met Jacob at an overcrowded Abba-themed dance night. He was wearing a faux-fur head wrap. He seemed so young. I was 33. Still, I thought he was cute. When we locked eyes on the smoking patio, I thought the feeling was mutual.
We got to chatting. Jacob said he worked “in music,” which I took to mean he sometimes played the guitar. He asked what I did, and I brushed off the question. I didn’t feel like talking about work.
A week earlier, my ex had moved out of our apartment. After six years together, he said, “Anna, I don’t think this is working.” And just like that, we were over. There were plenty of reasons. We argued too much, had different timelines for children. And then there was the sex — or lack thereof.
Couples therapy helped with the arguing but not the intimacy. When he finally handed me his key, I sat in my half-empty apartment and cried.
Now, with Jacob, I thought about how most of my friends were starting families and buying houses. And here I was at Abba Night, drinking a vodka soda.
He asked for my number. I gave it to him, not expecting much.
The next day, he asked if I wanted to get a drink. We met for margaritas. I was early. I realized that I barely remembered his face. All I knew was that he seemed young. As I waited at the bar, I wondered just how young. Finally, he appeared, looking like he was dressed for Coachella — baggy cargo pants and chunky, layered necklaces. I could barely meet his gaze.
He was 24, almost a decade younger. I was embarrassed, but Jacob shrugged.
“Age doesn’t matter,” he said.
Which of course, wasn’t true.
He told me he was a rapper and that his tracks had done well on Spotify. I was surprised. Impressed, even. He said a manager was interested, but he’d have to fork over a huge chunk of his profits.
I started to give him advice — as a TV writer, I had experience with predatory contracts. Then I stopped myself. Did I sound like his mother? We talked more. We didn’t have much in common, but I wasn’t ready to give up. When we finished our margaritas, I suggested a second bar.
The next place was swanky. The bartender gave me a funny look. Was he judging me? Maybe nine-and-a-half years wasn’t that much, but I’d never been on this side of an age gap. In my early 20s, I had dated a handful of older men. At the time, I found their age alluring, but hindsight had made me skeptical of their attraction. I once heard that adult brains aren’t fully developed until the age of 25. Was my young self simply easier to manipulate?
Sitting with Jacob, I wondered if now I was the creepy older man. I ordered myself an orange wine and he blinked. “What’s that?” he asked.
I explained it had something to do with the grape skins. He nodded blankly, then he asked what I was working on. I told him about my horror script about a girl who loses her mind in the woods. He listened, eyes wide. He told me it sounded “like a real movie.” I knew he meant it as a compliment.
Jacob was a gentle lover, if a bit nervous. He lingered in my living room for an hour before kissing me. I didn’t mind. He was a good kisser. And when he ran his fingers along my arm, the age gap disappeared. We were just two people on a fitted sheet, trying to feel less alone. For once, sex felt effortless.
On our second date, Jacob showed me his music. It was chaotic and loud. Even his voice — deep and full of swagger — felt unfamiliar. I didn’t understand it.
On our third date, lying naked in bed, I told Jacob I wasn’t looking for anything serious. I explained that I was emotionally unavailable because of my breakup. He said that was OK. Perfect, in fact. Because he wanted to focus on his music, not love. We agreed to keep things casual.
“Casual” meant seeing each other once a week. He always offered to pay, but usually I grabbed the check. I knew my TV writer salary exceeded his Spotify profits. He lived in a cramped studio apartment and slept on a futon. I had slept there once, but my back hurt so much from the flimsy cushions that I vowed never to do it again.
Two months in, we went clubbing with his friends in a sweaty basement bar where everyone seemed younger than me. I was dressed in high-waisted Zara jeans and a tank top I’d bought in 2017. The other women wore low-slung pants with tiny crop tops, oozing the kind of confidence you feel when you’re still on your parents’ health insurance.
One vented to me about her on-again-off-again boyfriend. I suggested couples therapy. She looked at me like I had told her to eat a shoe.
The next morning, I peered into my bathroom mirror, hyper-aware of the wrinkles on my forehead. I had turned 30 in the first year of Covid. Prepandemic, I didn’t remember ever having wrinkles. Post-pandemic, my face seemed centuries older.
After three months, I found myself falling for Jacob. On Valentine’s Day, I took him to my favorite sushi restaurant. Afterward, in bed, I told him how I felt. I said I didn’t need a serious relationship, but I wanted to take things to the next level. Maybe a weekend trip?
He grew quiet. “Maybe,” he said.
During our next date, Jacob dumped me. We had just ordered our entrees when he dropped the bomb, saying, “I think we should roll things back romantically.”
I didn’t get it. Was this about the weekend trip? He said it was everything. I never understood his jokes. We had different interests. And hadn’t we agreed to keep things casual? Didn’t I notice that when I told him I was falling for him, he never said it back?
The waiter returned with our entrees — salad for me, and a big bowl of mac and cheese for Jacob. Waiting for the bill, I wanted to cry, but I refused. It was one thing to date a 24-year-old in a faux-fur head wrap; it was quite another to get dumped by one.
That night, I couldn’t sleep. At 3 a.m., I opened Spotify and clicked Jacob’s first track. I listened over and over until the music no longer confused me. What had initially sounded chaotic now seemed urgent and driving.
I searched Spotify for similar artists. It was as if dating Jacob had opened my eyes to the fact that there was a new generation of people creating art, and it was worth trying to understand. Obvious, maybe, but I’d missed it.
Jacob and I had only dated a few months and barely scratched the surface of our emotions. We were, by all accounts, a “situationship.” And I had spent most of it focused on myself. Because I paid for things, I chose what we did, what we ate. And it wasn’t just that. He seemed endlessly impressed by my writing career. He made me feel like I had things figured out. But I hadn’t considered how it all made him feel. That maybe the constant focus on my life made him feel small and unmoored.
A month later, I willed myself onto the dating apps. When I met Jacob, I was reeling from heartbreak. But things had changed, and I had to admit that sex with anyone would now, inevitably, lead to feelings.
I soon matched with a guy named Lucas. He was 45, with eye wrinkles and gray hair in his beard. On our second date, he took me to a fancy restaurant and ordered the orange wine. He had just bought a house in Encino and redone the floors. After our fourth date, he suggested a weekend trip. Maybe Santa Barbara?
I liked Lucas, but what was I doing flinging myself so far across the age spectrum? Lucas wanted something serious. Was I ready for that? I told my therapist I was thinking of breaking it off. She asked why. I said, “Because he’s old!”
She laughed. “If you like him, that’s all that matters.”
I said yes to Santa Barbara.
A year after my breakup with Jacob, he texted me. He was now 25, meaning his brain had officially finished developing. When he asked if I would like to meet up, I was shocked. Did he finally realize that he couldn’t live without me? He clarified that he still didn’t want anything serious, but would I be interested in a no-strings hookup?
I politely declined. Lucas and I had plans.
Zoe Latta, a co-founder of the fashion brand Eckhaus Latta, saw the clock on Instagram and started searching for pharma swag on eBay. “It was just a hole I got in,” she said. Latta soon rounded up some examples at “Rotting on the Vine,” her Substack newsletter, describing them as “silly byproducts of our sick sad world.”
Pharma swag feels somewhat like Marlboro Man merch — “like this very specific modality of our culture that’s changed,” Latta said, adding, “At first, I thought it was ironic and cheeky. But it’s also so dark.”
In particular, swag like the OxyContin mugs that read “The One to Start With. The One to Stay With” is regarded as highly collectible and highly contentious. Jeremy Wells, a newspaper owner and editor in Olive Hill, Ky., remembered, for example, seeing the mugs sold at a Dollar Tree in New Boston, Ohio, in the late 1990s or early 2000s. “At the same moment that the epidemic is blowing up,” he said.
“You can do a chicken-and-egg argument, and I doubt very seriously that those mugs made anybody get addicted,” he said. “But I do feel like things like those mugs did add to the mystique and the aura of seduction.” (After a protracted lawsuit, Purdue Pharma, the maker of OxyContin, has been dissolved and is on the hook to pay more than $5 billion in criminal penalties for fueling the opioid epidemic.)
“I was surprised to see how much this stuff was selling for in general — there is demand,” Latta said, pointing to a vintage Xanax photo frame listed for $230. Latta said she could imagine buying it for a friend who takes Xanax on planes (“if it was at a thrift store for under $10”) or maybe a pair of Moderna aviator sunglasses that she found, which seem to nod at Covid vaccines and the signature Biden eyewear, she said.
Pharmacore — medical-branded pieces worn as fashion — has found new expression at the confluence of identity, medicine and commerce, and at a time when skepticism toward pharmaceuticals is at a high (see: the MAHA movement).
Goth Shakira wears a Blumarine jacket, vintage Jean Paul Gaultier top from Wild West Social House, Jane Wade bra and Ariel Taub earrings.
My ex-boyfriend, whom I just got out of a relationship with, had a pure heart and was a loyal lover. However, he lacked ambition and his family didn’t have the best values. I don’t see myself raising children with him because I don’t want my kids to be surrounded by his family. (I broke up with him on the night of his birthday because his sister got violent with me.) We dated for over a year and I’d always be the one to take care of the check when we’d go out on dates. He had no network, so we would always hang out with my friends and colleagues. Am I wrong for leaving him? Is his loyalty worth going through all that?
Girl. (“Girl” is a gender-neutral term of endearment, by the way.) I’m going to need you to take a deep breath, look at your gorgeous self in the mirror and relish in the fact that you have made the right decision.
First, let’s focus on the good. Loyalty and purity of heart are beautiful traits that many, many people on this earth have. When you find someone who does, and then combine that with your attraction and attachment to this person (along with the reality that many, many people also lack these traits), it makes sense that you’d be feeling like your ex is a rare find that you might not encounter again. However, you can care for someone, and also acknowledge the truth that the life they are setting themself up for is not the life you envision living — or, crucially, the life that you envision your children living. A long-term partnership is so much more than love. It requires a shared vision for fulfillment and happiness, based on compatible values. It necessitates a wholeness from both parties, wherein two individuals take ownership and accountability over their own success and well-being. It is loving to let someone go so they can live their life in peace and free of judgment, and even find someone else whose version of an ideal life more closely matches theirs. Most importantly, letting someone go who you know is not aligned with the life you want to live is a deeply self-loving act.
The meaning I glean from your words is this: It’s not so much that you yearn for him romantically and fear you made a mistake simply because your life is empty without him. (In fact, it sounds like you were the one adding a lot of value to his otherwise limited existence through your resources.) It seems that you feel guilty for leaving him behind as you went on to pursue a better life for yourself. That kind of feeling is more caretaking, and dare I say maternal, than loving (at least the kind associated with romantic partnership). He’s your ex, not your son. Unconditional love is only healthy and appropriate in the context of a parent-child relationship, and that’s not the situation here. People who engage in romantic relationships with men — women, femmes, gay men, etc. — are socialized to be ever-forgiving, to have infinite patience and compassion. The lines get blurred when you do feel kindness and genuine compassion for someone you care about. It can be difficult to discern when you’re being too harsh, and when you’re just setting a healthy boundary. Society makes it difficult for us in that way. But we don’t have to succumb to that pressure.
You can’t fall in love with someone’s potential. If a person, especially a man, shows up to a relationship as someone you can’t envision spending an extended period of time with, then that’s not your person. Not only is it impossible to truly “fix” or “change” anyone, it’s simply not an efficient or productive use of your precious energetic and material resources. Of course, we all change over time, and hopefully in positive ways. But that change needs to be self-directed, coming from within each individual. “Change” exerted on another through force robs the receiving party of the dignity of authoring their own life path. Even the verbiage of your question indicates that you’ve already extended a lot of generosity and patience toward someone who didn’t feel like working toward social and financial independence, and setting boundaries with their family should have been a top priority. I can sense your exhaustion underneath the guilt. That’s the root of the matter. And what matters is you.
I can sense your exhaustion underneath the guilt.
Loss is just space. It can hurt and feel empty at first. But it also allows you the room you need to expand your world with abundance, not shrink it and drain it into scarcity. Affirm in your heart and in your mind that love itself is an infinite resource. If you channel the patience and generosity that you once put into your ex into a life where you are fulfilled to the utmost, the right person (or people) will find you.
And, girl. Some time from now, when you are loved by a man who takes his own dignity seriously, and supports you in the feminine energy of rest and calm that you deserve to experience and embody, you will be so grateful to this current version of you that had the courage to let go. I’m proud of you.
Photography Eugene Kim
Styling Britton Litow
Hair and Makeup Jaime Diaz
Visual Direction Jess Aquino de Jesus
Production Cecilia Alvarez Blackwell
Photo Assistant Joe Elgar
Styling Assistant Wendy Gonzalez Vivaño
The kiss finally happened at a Halloween party Chatterjee hosted at her apartment, while the two were watching “American Psycho” on the couch at 3 a.m., when everyone else had gone out for food. “We’re sitting so close our legs are touching and I’m freaking out,” Braggins said.
“I looked at Abby, and I was like, ‘I’d rather kiss you than watch this,’” Chatterjee said. So they did. About a month later, they were official.
On April 10, Braggins suggested they take a trip to Home Goods in Brooklyn. When they ended up at Coney Island Beach instead, Chatterjee was none the wiser. It was an early morning, so the two, along with the dog they adopted together, Willow, enjoyed having the beach to themselves.
Braggins ran ahead with Willow and crouched behind some rocks. When Chatterjee got a glimpse of Willow, there was a bandanna tied around her neck. It said, “Will you marry me?” Braggins pulled out a shell with a ring in it. The answer was yes.
A few days before, Chatterjee had proposed to Braggins amid a gloomy, cloudy sky on top of the Empire State Building.
The two were married on April 21 at the New York City Marriage Bureau, in front of three guests, by Guohuan Zhang, a city clerk. Afterward, they celebrated at Bungalow, an Indian restaurant in the East Village, with a few more friends.
Though Chatterjee’s parents were not present at the wedding, one of the couple’s most meaningful moments came in 2023, when Braggins traveled to India to meet Chatterjee’s family for the first time. Chatterjee had never brought a partner home before, and she had warned Braggins that same-sex relationships were still not widely accepted there. But by the end of the trip, Chatterjee’s mother had embraced Braggins as family, telling her, “I have two daughters now.”
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