By Josh Gondelman — 17 Aug 2026

#197. Pumpkins Already and You

You've gotta call these "StackING Pumpkins" or else they sound like pumpkins with big boobs sorry.

Hi everyone,

While some work stuff was coming together, I had a pretty fun and loose week. Tinkered with new standup bits and other projects at a leisurely pace. Did a little cooking. Attended a dinner party and a karaoke night. I'm back recording episodes of The Nightly–the bedtime podcast I host for Hatch–this week, which I'm excited for. We've transitioned the show to be a listener call-in program, which has been really cool to be a part of. If any readers have a little weird thought that they think about at night and want to discuss, you can send an email or voice memo to thenightly@hatch.co or leave a voicemail at the show's phone number: (904) 644-4859. I've had some really fascinating conversations with listeners about topics ranging from who designs mascots to going through life with too expressive a face.

Maris and I tore through Season 1 of Sugar (an Apple show starring Colin Farrell as a noir-style detective in present day Los Angeles, which sounds made up even without revealing the big twist). The twist was spoiled for us a while back, which was a relief because we had watched the pilot episode two years ago and gone "What the hell?" and gave up until we found out what the hell. We jumped back in after talking to my parents who had watched both seasons and enjoyed it a lot. We're in the middle of Season 2 now and have no regrets about learning the spoiler. If anything, it helped me lock into the tone of the whole thing. Semi-relatedly, I really like how considerate the character of John Sugar (yes, that's his name) is. He's a little like Patrick Swayze in Roadhouse, which is OBVIOUSLY a compliment. He's also a little like Jake Gyllenhaal in Roadhouse but for other reasons!

The wonderful Richard Lawson and Alison Willmore invited me onto their podcast Critical Darlings to talk about the movie One Night Only aka Sex Purge. If you haven't heard about this film, it's a rom-com set in a near-future dystopia wherein unmarried people are only allowed to have sex on one night of the year. We had a really fun and thoughtful conversation about this preposterous movie. Maris and I did enjoy Sex Purge, but mostly when it basically ignored its own premise. What I forgot to say on mic was that we saw One Night Only under unexpectedly ideal conditions: A noon baby-friendly showing where three new moms directly in front of us were drinking wine, and someone just to our right was giving sparing (and also unsparing) commentary throughout. At one point, one character says "I just don't want this moment to end..." and our seat neighbor replied "I do!" Perfect Tuesday afternoon moviegoing experience seeing a far-from-perfect movie.

I also recorded an episode of Mindy Tucker's podcast Mindy's Comedy Archives a little while back, and it's out today. Mindy is a truly brilliant photographer. We have shot three album covers together, and my book cover was an extra snap from a headshot session that she just happened to have lying around, such is her genius. Everyone looks their best in a picture Mindy takes because she's so talented technically but also SO warm and lovely and makes people feel extra safe and at ease. The structure of the podcast is that Mindy prints out every picture she's ever taken of her guest and then has a chronological discussion about their time in the New York City comedy scene.

Mindy and I recorded on a day we found out our friend John Rosenberger had died, and our conversation got a little heavy as we discussed how many of our late friends Mindy's work has been used to memorialize. I got pretty emotional, especially when we got to the photo of me doing the hora with Kevin Barnett at Mike Lawrence and Adina Pliskin's wedding. It was a really beautiful experience to get to sit with Mindy for so long and to do so much reminiscing, even though we only made it through the pictures from 2015 or so! I hope listeners/viewers find the conversation to be interesting too!

This Sunday I'll be part of a show at Caveat on the Lower East Side called Comedians Interview Experts. I'm the comedian, thank goodness, and I'll be interviewing doctor Kelly Weinersmith about people who have self-infected with various parasites for research purposes. It's weird and fascinating stuff. I can't wait to learn more!

And on the 27th, I'm hosting a What's New? show at Union Hall in Brooklyn. I haven't done one of these in a long time, and I'm very excited. The premise of the show is: I do a bunch of new/new-ish jokes and see how they go! But I also book special guests. This edition of the show features my friend Maddie Connors who's in town from LA for the month as well as my friend Janesh Rahlan, who is ALSO visiting from LA. Plus more! Hope to see you there!

Tonight I'll be hanging out at Frankenstein's Baby at Union Hall where the show will have an ASL interpreter! Extremely cool! Alison and Tyrone are hosting, and I'm excited to see what they get into!

PEP TALK FOR PUMPKINS ALREADY

"Stacked Pumpkins" on a shelf from a Five Below in Brooklyn. They are plastic Halloween decorations. — Pumps like a truck, truck, truck. Is that anything? No, right?

Pumpkins, I love you but you've got to take it down a notch.

It's only the middle of August, and I'm seeing you and your skeleton friends all over the place. Frankly, I've got less of a problem with the big bonefolk decorations since you can dress them up for all seasons. Swimming trunks dangling from the exposed ball and socket joints of their plastic hips in the summer. Santa hats perched askew on their knobby skulls in the winter. Dead people stay dead all year long, so why not memento a little mori with a fun tower of tibias and vertebrae decorated for the moment we're in.

But pumpkins! You are an incontrovertibly autumnal occurrence. I feel chronologically dizzy seeing your bulbous orange bodies popping up before the local public schools have commenced their fall semesters.

My problem isn't even with pumpkin pumpkins, which don't exist fully formed yet. If the patches were popping with adult sized gourds right now, I'd accede them the cultural and physical space they've claimed. Weirdly, I don't even care about the premature return of "pumpkin spice." Let people enjoy their synthetic flavors any time of year, I say, as someone who wishes peppermint stick ice cream were widely available 24/7/365. It's the plastic pumpkin pails and the cardboard pumpkin cutouts that get me. Why do we need them now? People won't forget about Halloween if they don't see the decorations on sale until mid-September. It's not the kind of thing people need to get two and a half months of use out of to feel like they got their money's worth.

I don't normally get riled up about humans defying nature. There is nothing natural about a commuter train, and I find those vastly preferable to finding a horse to ride across town. I love iced coffee, which does not occur in nature, and the lack of abundant ice is a clear victory for the United States over Europe at a time when my home country needs any edge we can get.

The problem isn't that August pumpkin ephemera is unnatural; it's that it takes the anticipation out of the future by collapsing the calendar. On a long enough timeline, we will start to see full price candy corn on the shelves on November 1st in advance of the following October. What's the rush? Why are our holidays #hustling and #grinding? Can we not wait for anything anymore?

We are encouraged to binge television shows over a weekend, to order groceries delivered instantaneously despite admittedly inhumane conditions, to text and drive at the same time. Not every element of our lives has to be simultaneous or on demand! Why can't we wait for pumpkins to be available before we demand pumpkins??!?!

I understand that this is an Andy Rooney-ass complaint, and that even referring to Andy Rooney makes me an old man yelling at a cloud about another old man. And maybe Halloween decor isn't going on sale earlier, and I'm fabricating details in my mind about at not-so-long-ago period when October weather was less like August weather. It's possible that I'm imagining that summertime department store displays were backpack and lunchbox centric.

But pumpkins, it's not your time yet! We are not only willing to wait for you, we're impatient for waiting! You don't have to show up early, and we'll be okay if you stay a few days late! It only makes a jack of the lantern (formal name) scarier.

PEP TALK FOR A READER

I've done some light edits on this request and appended the nickname.

I am usually the one with answers, but my friend is talking about her new friend a lot. “Terry” this and “Terry says” etc. She is obsessed with them. “Terry” is a chat bot. When I ask my friend what SHE thinks, she defers to Terry. Help!
- Terry-fied

If we're going to start by looking on the bright side, let's give kudos to your friend for helping to close the gender gap in AI chatbot use. More and more women are out there letting robots do it for themselves! On the other hand, that means we've found a way to make equality kind of bad! "In this house we believe...serial killers can be any race or gender...refugees should get to drive drunk once a week as long as they don't get caught..."

On occasion, I have gotten a little annoyed with a friend of mine telling me all about another friend of theirs who is so cool and smart. If Eric is so cool, how about you stop gatekeeping that friendship! Let me into the friend zone too! But that feels infinitely less frustrating than your pal constantly referring to their new buddy who doesn't even exist.

A chatbot, of course, is not anyone's friend. Giving one a human name probably makes you sympathize with it too much in the same way that farmers have trouble slaughtering animals that they have decided to call "Bessie" or "Dr. Oinkers." But any connection someone might feel to a large language model is, at most, like having a digital entourage. And if I learned anything from half-watching the 2015 documentary Entourage in the green room before a comedy show, blind allegiance and sycophancy are not beneficial to your life or movie career. Although I do weirdly think that if every LLM had more of a Johnny Drama personality (always messing things up by being too dumb and horny), it would be harder for people to be taken in by their obsequiousness.

You do not have to listen to your friend talk about their Computer Turtle any more than you are obligated to allow them to continue to complain about a situationship they're three years into with no admission that they should, just maybe, call it off. Actually, you're LESS obligated to listen to anecdotes about "Terry" because despite the fact that "Terry" always texts back right away, he or she doesn't actually exist. And that's even worse than a real person who's (to employ the parlance of the early aughts) just not that into you(r friend).

People talk a lot about "fake friends." Drake raps about the concept all the time, despite seeming like that absolute number one celebrity who would consider a chatbot he named "Sauvignon" to be his closet confidante. But your friend has a literal fake friend. And either she will get hip to the fact that you don't want to hear about their imaginary adventures and good times, or she will choose "Terry" over you, and spend her time putting on little online puppet shows for herself.

You have so much more to offer than "Terry" does. You can help your friend move. You can tell your friend hard truths when necessary. You can help drive on a road trip or bring soup to her house if she's feeling sick. And you may ask the same of her, but that's what friendship is. Even Vincent Chase knows that, and he isn't real either.

PICK-ME-UP SONG OF THE WEEK:
Phil Collins - "Something Happened On The Way To Heaven"

I grew up in a Genesis-heavy household, especially once my parents purchased a CD player and joined the BMG Music Club to help build our library. (Obviously I mean Genesis the Peter-Gabriel-and-later-Phil-Collins-fronted band, not Genesis the book of the Bible.) But I did not recognize this song when friend of the newsletter Rachel Syme sang this at karaoke Maris, to her credit, knew it immediately.

"Something Happened On The Way To Heaven" sounds cheesy now, but I can't tell if it sounded cheesy in 1990 when it was released. It sounds like part of the cast recording of a musical about Phil Collins starring Phil Collins. There's an instrumental break that would be perfect for a couple of measures of tap dancing. Same goes for the intro. I do kind of wish we had big, slightly silly songs like this now. I mean, I wish people still made them. We still have all the old ones, and it's fun to think about how many there are left to discover. Yesterday's overpolish is today's borderline camp. So maybe it just takes time for this song to age into being a delightful stone to turn over and not a glossy annoyance on the Billboard charts.

I have always loved that Phil Collins is a drummer AND a singer. He's like: "You bastards aren't going to make all the notes without me. If I can't make them with my hands, I'm going to do them with my mouth." That's fun.

Honestly, you should reallllly give Open Mike Eagle and Kenny Segal's new album DOOMED! a listen though!!!! It's great!