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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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‘Wait Wait’ for April 18. 2026: With Not My Job guest Phil Pritchard

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‘Wait Wait’ for April 18. 2026: With Not My Job guest Phil Pritchard

Phil Pritchard of the Hockey Hall of Fame works the 2019 NHL Awards at the Mandalay Bay Events Center on June 19, 2019 in Las Vegas, Nevada. (Photo by Bruce Bennett/Getty Images)

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This week’s show was recorded in Chicago with host Peter Sagal, judge and guest scorekeeper Alzo Slade, Not My Job guest Phil Pritchard and panelists Alonzo Bodden, Adam Burke, and Dulcé Sloan. Click the audio link above to hear the whole show.

Who’s Alzo This Time

The Don Vs The Poppa; World’s Worst Doctor; Should We Eat That?

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Panel Questions

Big Cheese News!

Bluff The Listener

Our panelists tell three stories about someone missing a huge opportunity in the news, only one of which is true.

Not My Job: Phil Pritchard, the NHL’s Keeper of the Stanley Cup, answers three questions about the other NHL, National Historic Landmarks

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Peter talks to Phil Pritchard, the NHL’s Keeper of the Stanley Cup. Phil plays our game called, “Let’s Go Visit The NHL” Three questions about National Historic Landmarks.

Panel Questions

The Trump Dump and Air Traffic Control Becomes Animal Control

Limericks

Alzo Slade reads three news-related limericks: Spice Up Your Spring Cleaning; A Fizzy Meaty Drink; The Right Way to Eat Peeps.

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Lightning Fill In The Blank

All the news we couldn’t fit anywhere else

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Our panelists predict the next big AirBnB story in the news

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How to have the best Sunday in L.A., according to Paul W. Downs

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How to have the best Sunday in L.A., according to Paul W. Downs

Paul W. Downs can’t help it that even on the weekends, his life intersects with “Hacks,” the HBO comedy he co-created and co-showruns with his wife, Lucia Aniello, and their friend Jen Statsky. (He also appears on the show as Jimmy LuSaque Jr., the besieged manager of its two stars, played by Emmy winners Jean Smart and Hannah Einbinder.) The fifth and final season of “Hacks” premiered last week, but on Downs’ days off, he often finds himself at its previous filming locations or hanging out with cast members who have become like family.

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In Sunday Funday, L.A. people give us a play-by-play of their ideal Sunday around town. Find ideas and inspiration on where to go, what to eat and how to enjoy life on the weekends.

Downs moved to Los Angeles in 2011, but soon after, he and Aniello were hired to write (and for him to act) on the über-New York show “Broad City,” keeping them away from the West Coast for years. Now the couple live in Los Feliz, which they enjoy with their young son.

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“I love Los Feliz because it’s a real neighborhood with restaurants and bars, but also feels close to nature with Griffith Park,” Downs says. “Also it’s very central to my Eastside friends and Westside agents.”

And if he had to live at a local mall, like the character Ava Daniels did in the third season of “Hacks,” which would he choose?

“It would be the Americana, obviously.”

Here’s how he’d spend a perfect day in L.A.

10 a.m.: A late rise and a li’l barista

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I’m sleeping in if I can, which I can’t because I have a toddler, but let’s say I can sleep ’til 10. That would be insane.

Then I’m making coffee at home. I’m making it with my 4-year-old because he likes to make my coffee now. He always wanted to help, now he really wants to do it on his own. I’m still there to supervise, but he does do a lot of it.

I do batch brew. I’m doing Verve Coffee that I’m grinding there, and then I’m brewing four cups because I need my coffee. I had a Moccamaster for a long time, but I recently got a Simply Good Coffee. There’s no plastic — it’s all glass and metal.

11 a.m.: Chocolate croissants for everyone

We’re driving to Pasadena and we’re going to [Artisanal Goods by] CAR, which is the place to get the best chocolate croissant, I think, in the world. I don’t just think in L.A., I think they’re better than Paris. I’m going there with my wife and my kid and I’m having another coffee and some pastry. We’re ordering three [chocolate croissants]. We’re not doubling up.

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11:45 a.m.: The family business

We’re driving to Fair Oaks in Pasadena. There’s a place called T.L. Gurley. We shot “Hacks” there, actually. Not only in Season 1, but also full circle in Season 5. We’re going to shmay around and look at antiques. My kid is going to want to play a vintage pinball machine. We’re going to find a little piece of art for the house or what have you. It’s not necessarily that I’m on the hunt. It’s to pass the time and to have some fun. If I could do anything and have a leisurely day and take my mind off work, that’s what I’m doing.

People love to interact with my kid when he’s there. We’re really training him to appraise things at a young age. My parents are part-time dealers of antiques. My grandmother bought and sold antiques. It’s kind of a family business.

1:30 pm.: Baguettes and books

We’re driving to Larchmont and we’re getting a sandwich at Larchmont Village Wine, Spirits & Cheese. I’m doing prosciutto-mozzarella-basil on a baguette.

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Then we’re going to Chevalier’s Books. What’s sad is that I’m often not looking for leisure material. I’m looking for something that I’m interested in learning more about or writing about, or that they’re turning into a show I want to audition for. But we’re also doing Little Golden Books for my son. He’s obsessed. We’re not huge on screen time, so we really encourage the book-buying.

2:30 p.m.: Cast pool party

We’re having some family fun in the pool and we’re doing that until evening. We invite people over all the time. My sister-in-law is a New Yorker, but she actually wrote last season on “The Rooster” and she’s often writing on shows in L.A., so she’s often here and she’ll have a couple friends come over. I know this sounds like a piece of PR or something, but we’ll really literally have Hannah [Einbinder] and maybe Mark Indelicato from “Hacks” come over to swim. Jen, our co-creator of “Hacks,” will come over.

6:00 p.m.: Family dinner

Sometimes we’ll order Grá to the house, which is a pizza place in Echo Park — excellent sourdough crust pizza. But if we don’t do that, an ideal evening is an early dinner at All Time on Hillhurst in Los Feliz. We’re ordering the ceviche and my son is having all of it and not sharing with anybody at the table.

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8:45 p.m.: A thrilling ending to the day

After putting my kid to bed, my wife and I, in an ideal world (full disclosure: we haven’t done this in two years), we’ll watch something together that we’ve been meaning to watch. We have a long list of movies and we either want to revisit or that we haven’t seen that we need to watch.

We don’t watch a lot of comedies. It’s a dream to watch a “Black Bag” or a little espionage thriller. We really like that because it’s so different than the stuff that we’re working on in the day.

Often the things we watch are things that we admire. We like deconstructing it as fans of film and television. We do like talking about the making of it, but it’s less of a critique and more of a listing of the things we appreciated about it.

10:30 p.m.: No work tomorrow

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And then it’s lovemaking ’til morning on a perfect Sunday. If it’s a perfect Sunday, there’s also a Monday that’s off.

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Sitting in a jail cell, alone and hopeless, a man’s life is suddenly changed

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Sitting in a jail cell, alone and hopeless, a man’s life is suddenly changed

Jay (not pictured) found himself alone and hopeless in a jail cell when a fellow inmate’s unexpected words of comfort changed his life.

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When Jay was 22 years old, he was a self-described loner. In this story, he is being identified by his nickname to allow himself to speak candidly about the following experience and his mental health. He says the few people he did hang out with at the time had questionable morals.

 ”I chose my friends poorly, and your friends have a tendency to rub off on you. And so I started making poor decisions,” Jay said.

One evening, when he and his friends were out drinking, someone suggested they should try to break into the chemistry building on his college campus. Most of the group shrugged the suggestion off, deeming it impossible, but Jay was convinced he could pull it off.

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“The next night I made a plan of how to do it, and I did it,” Jay remembered. “And I didn’t get caught doing it, [but] I got caught afterwards.”

At around 1 that morning, Jay was placed in the county detention center. Sitting alone in his cell, reality began to sink in.

“I pretty much thought that my life as I knew it was going to be over, and I had decided that the world would be better off without me in it.”

Jay made a plan to end his life. As he prepared himself, he began to cry.

“But just in that moment when I was ready to do it, I heard a voice coming from the top left corner of my cell, from a little vent. And someone called out to me and said, ‘Hey, is this your first time?’”

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The man who called out was an inmate in the cell next door.

“I collected myself a little bit, and I said, ‘Yeah.’ And he said, ‘Can I pray for you?’”

Jay had grown up religious, but had stopped going to church years before. In that moment, though, he knew he needed support. He said yes, and listened as the man began to pray.

“I wish I could tell you that I remember the [exact] words that he said to me, but what I remember is that his words landed with me, and instead of wanting my life to be over, suddenly I saw hope,” Jay said.

The interaction happened nearly ten years ago, but it was a pivotal moment in Jay’s life, and one he thinks about all the time.

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“[Now], I have a good job. I have a girlfriend who loves me. I have a life. But I have a life because somebody who was in the same situation I was in had the courage to talk to a fellow inmate and be kind.”

Jay says that he wishes he could meet that man again and express his appreciation.

“[I would] shake that guy’s hand, give him a hug, and tell him what his small gesture meant for me, how he changed the course of my life.”

My Unsung Hero is also a podcast — new episodes are released every Tuesday. To share the story of your unsung hero with the Hidden Brain team, record a voice memo on your phone and send it to myunsunghero@hiddenbrain.org.

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