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Ode to a Gen-Z Situationship

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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.

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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.

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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.

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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.

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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.”

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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.

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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.

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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.

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‘The Rest of Our Lives’ takes readers on a midlife crisis road trip

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‘The Rest of Our Lives’ takes readers on a midlife crisis road trip

The midlife crisis remains a rich vein for novelists, even as its sufferers skew ever older.

In Ben Markovits’ 12th novel,The Rest of Our Lives — which was a finalist for this year’s Booker Prize the narrator, 55-year-old Tom Layward, is trying to figure out what to do with his remaining time on this mortal coil. With his youngest child headed off to college, his health faltering, and both his marriage and law school teaching position on the rocks, he feels blocked by “undigested emotional material.”

So, what does he do? In the great American tradition, Markovits’ wayward Layward hits the road. After dropping off his daughter at college, he heads west into his past and what may be his sunset.

America’s literary highways are not quite bumper-to-bumper, but they are plenty crowded with middle-aged runaways fleeing lives that increasingly feel like a bad fit. Many are women, including the heroines of Anne Tyler’s Ladder of Years  and Miranda July’s All Fours. But there are men, too, like the hero of John Updike’s Rabbit, Run — the granddaddy of midlife crisis novels — which serves as a sort of template for Markovits’ novel (and, tellingly, is the subject of his narrator’s abandoned doctoral dissertation, which he tossed aside for the more dependable employment prospects of a law degree after meeting his “unusually beautiful” future wife, Amy.)

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We meet Tom and Amy on the cusp of empty nesting. This is not a happy prospect. Tom has been biding his time for the last dozen years, since he learned of Amy’s affair with a guy she knew from synagogue. This happened back when their daughter, Miriam, was six, and her older brother, Michael, was 12.

Their marriage has not improved in the intervening years. The early pages of this novel, a countdown of the Laywards’ last few days as a family unit before Miri matriculates, recalls an old magazine feature: “Can this marriage be saved?” One would think not. Amy, forever trying to provoke a reaction from her impassive husband, jabs repeatedly, “You really don’t care about anything, do you?”

Tom observes that staying in a long marriage requires acceptance of reduced expectations. He notes wryly: “It’s like being a Knicks fan.” (Like Markovits and Updike’s Rabbit Angstrom, Tom is a former basketball player. Amusingly, his description of each character includes a height estimate.)

Driving west, Tom has plenty of time to ponder his disappointments, and Amy’s. He notes that she had hoped he’d be more ambitious; she wanted him to accept a lucrative offer from a top litigation firm that would have paid for private school for their kids. Instead, Amy says, he chose to stay in his “dead end” job at Fordham Law, where he teaches a controversial class on hate crime. He is currently in hot water for his legal input for the defense in a case against an NBA owner for racial allegations. Amy’s take: “Tom loves to stand up for racists.”

Tom’s road trip takes him on a desultory odyssey visiting old friends and family. He finds their lives disheartening. In Pittsburgh, a grad school friend who became an English professor teaches “dead white men” and is having an affair with a graduate student. In South Bend, his younger brother is distressed over limited access to his kids after a divorce. In Denver, a college teammate urges him to see a guy at UCLA who wants to bring a case about systemic discrimination against white American basketball players.

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His old high school girlfriend, who leads a busy life in Las Vegas as a single, late-life parent, urges him to steer clear of the case. When she also tries to talk about his alarming health symptoms (puffiness, breathlessness), he stonewalls her. “I forgot what you’re like,” she tells him, eerily echoing Amy. “You don’t really care about anything.”

At each stop, Tom tries to put a good face on his trip by telling his hosts that he’s thinking of writing a book about pickup basketball across the country. He also confesses, “I may have left Amy.” “You may?” his brother says.

Tom exacerbates Amy’s longtime presentiment of abandonment by ignoring most of her calls. Periodically, he checks in late at night, and they circle around what’s going on. “God, you’re cold,” she says when his explanations leave her wanting. His response? “Okay.” When he confides that he’s feeling “a little adrift…I can’t seem to get a grip on anything,” she surprises him by responding, “Me neither.” It’s a start.

In a 2006 interview with Yale Daily News, Markovits’ alma mater, he said, “I like to write about what it is like to become happier, although no one has ever been able to spot happiness in my books.”

You don’t have to look too hard to spot glimmers of happiness behind the missteps and misconnects in this ultimately moving probe of life, love, family and marriage across years and miles.

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Guess Who This Racing Enthusiast Is!

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Guess Who This Racing Enthusiast Is!

Guess Who
This Racing Enthusiast Is!

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Springsteen’s label was about to drop him. Then came ‘Born to Run’

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Springsteen’s label was about to drop him. Then came ‘Born to Run’

Biographer Peter Ames Carlin describes the making of Born to Run as an “existential moment” for Springsteen. Carlin’s book is Tonight in Jungleland. Originally broadcast Aug. 7, 2025.

Hear the Original Interview

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