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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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Wagner Moura on ‘The Secret Agent,’ aging and privileging joy : Wild Card with Rachel Martin

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Wagner Moura on ‘The Secret Agent,’ aging and privileging joy : Wild Card with Rachel Martin

A note from Wild Card host Rachel Martin: After watching the Brazilian film “The Secret Agent,” I came away with a deeper appreciation for how much fear, resolve and longing can be communicated through a person’s eyes.

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White House To Ilhan Omar
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‘Dawson’s Creek’ star James Van Der Beek has died at 48

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‘Dawson’s Creek’ star James Van Der Beek has died at 48

Actor James Van Der Beek arriving at the Emmy Awards in 2019.

Valerie Macon/AFP via Getty Images


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Valerie Macon/AFP via Getty Images

James Van Der Beek — best known for his role as Dawson Leery in the hit late 1990s and early aughts show Dawson’s Creek — has died. He was 48. Van Der Beek announced his diagnosis of Stage 3 colon cancer in November 2024.

His family wrote on Instagram on Wednesday, “Our beloved James David Van Der Beek passed peacefully this morning. He met his final days with courage, faith, and grace. There is much to share regarding his wishes, love for humanity and the sacredness of time. Those days will come. For now we ask for peaceful privacy as we grieve our loving husband, father, son, brother, and friend.”

Van Der Beek started acting when he was 13 in Cheshire, Conn., after a football injury kept him off the field. He played the lead in a school production of Grease, got involved with local theater, and fell in love with performing. A few years later, he and his mother went to New York City to sign the then-16 year old actor with an agent.

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But Van Der Beek didn’t break out as a star until he was 21, when he landed the lead role of 15-year-old Dawson Leery, an aspiring filmmaker, in Dawson’s Creek.

Van Der Beek’s life changed forever with this role. The teen coming-of-age show was a huge hit, with millions of weekly viewers over 6 seasons. It helped both establish the fledgling WB network and the boom of teen-centered dramas, says Lori Bindig Yousman, a media professor at Sacred Heart University and the author of Dawson’s Creek: A Critical Understanding.

Dawson’s really came on the scene and felt different, looked different,” Bindig Yousman says.

It was different, she points out, from other popular teen shows at the time such as Beverly Hills, 90210. “It wasn’t these rich kids. It was supposed to be normal kids, but they were a little bit more intelligent and aware of the world around them … It was attainable in some way. It was reflective.”

The Dawson’s drama centered around love, hardships, relationships, school and sex — sometimes pushing the boundaries when it came to teens discussing sex. Van Der Beek’s character Dawson was a moody, earnest dreamer, sometimes so earnest he came across as a “sad sack,” says Bindig Yousman. He had a seasons long on-again off-again on-screen relationship with his best friend Joey, played by Katie Holmes. Bindig Yousman says Van Der Beek quickly became seen as a heartthrob.

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“I think he was very safe for a lot of tweens, and that’s when we started to get the tween marketing,” she says, referring to the attention paid to him by magazines like Teen People and Teen Celebrity. “And so because he wasn’t a bad guy, he was conventionally attractive … He definitely appealed to the masses.”

Dawson’s Creek launched the careers of not just of James Van Der Beek, but his costars Katie Holmes, Joshua Jackson and Michelle Williams. All went on to have successful careers in the entertainment industry.

Despite his success, Van Der Beek didn’t land many roles that rose to that same level of fame he enjoyed in Dawson’s Creek. Perhaps because audiences associated him so much with Dawson Leery, it was difficult to separate him from that character.

Still, he starred in the 1999 coming of age film Varsity Blues, as a high school football player who wants to be more than just a jock. In 2002’s Rules of Attraction, he played a toxic college drug dealer.

And he actually parodied himself in the sitcom Don’t Trust the B—- in Apartment 23. In it, he’s a self-obsessed actor unsuccessfully trying to get people to see him as someone other than the celebrity from Dawson’s Creek. In an episode where he decides to teach an acting class, the students ignore the lesson and instead pester him to perform a monologue from the show.

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In real life as well, the floppy blond-haired Dawson Leery is the one that stole fans’ hearts, but Bindig Yousman says Van Der Beek still enjoyed a strong fanbase that followed him to other shows, even when they were only smaller cameos.

In the 2024 Instagram post about his cancer, Van Der Beek said “Each year, approximately 2 billion people around the world receive this diagnosis … I am one of them.” (There were about 18.5 million new cases of cancer around the world in 2023, a number that researchers say is projected to rise.) Van Der Beek leaves behind six children.

The cast of Dawson’s Creek reunited to raise money for the nonprofit F Cancer, which focuses on prevention, detection and support for people affected by cancer. They read the pilot episode at a Broadway theater in New York City in September 2025. His former co-star Michelle Williams organized the reunion. James Van Der Beek was unable to perform, due to his illness, but contributed an emotional video that was shown onstage. In it, he thanked his crew and castmates, and the Dawson’s Creek fans for being “the best fans in the world.”

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