By Josh Gondelman — 29 Sep 2025

#151. AI "Friends" and You

Ayyy, I think this is bad!

Hi everyone,

It's been a huge week for me, not because anything exceptional happened, but because I tested negative for covid and rejoined the general public. I was so happy to be in the same room with Maris and Maggie the Pug without a mask on! One night, we went out for burgers and martinis in the neighborhood! I'm back, baby!

Burger from Liar Liar in Brooklyn. — Outstanding pickle situation here.

I've been trying to take it easy-ish, spending most of my time close to home and not kicking my own ass to start any big new projects. But I did end up doing a bunch of structurally disparate and creatively fortifying comedy shows! I performed a standup set on Gary Gulman's Pizzazz night at my home base Union Hall (where I have a bunch of stuff coming up), which was a great way to get back onstage after a short involuntary absence. Gary is one of the best working standup comedians, and his crowds are so fun and attentive! On Saturday night, another friend of the newsletter Josh Sharp invited me to join him opening for his brother's band (Mipso, who make beautiful folk music) when their farewell tour stopped in Brooklyn. Performing for a music crowd can be great, but it can also be a complete nightmare if the crowd hasn't arrived yet or even worse, they have populated the room but have decided to talk over you out of sheer indifference, which is possible if there's enough of them even when you have a microphone. It gets even worse than that sometimes, if you've ever heard Bobcat Goldthwait's stories about opening for Nirvana. Mipso's fans were extremely generous laughers and totally on board with a comedy showcase (Josh, me also Josh, Sabrina Wu, and Jay Jurden). Also, I'm a sucker for a backstage pass! It makes me feel like a real insider!

Music Hall of Williamsburg sign. — That's where I was! Thanks for having me, Josh and Mipso!

I also did a standup set on Chris Gethard's variety show THAT SHOW at UCB. Chris is one of comedy's great orchestrators and curators of barely contained chaos, which I mean as a compliment. The show involved a house band, numerous clown performances, Def Comedy Jam legend Alonzo "Hamburger" Jones, and a dozen performers in their underwear entering and exiting like a Benny Hill sketch. Amidst all the explosive creativity, which included Hamburger sitting in on drums with the band for a minute or two, I felt pretty square (I think I described myself on stage as "if seltzer was a guy"), but Chris creates such a welcoming space for all these different types of performance to exist side by side, and I had a really great time (despite DESPERATELY needing to start working on more new jokes for my own sanity).

Then Saturday night I got to be a part of Jeremy Kaplowitz and Phil Jamesson's live table read for their fantasy pilot The Chronicles of Trevor. I played the title character, a slick management consultant sucked into a Narnia-type world full of weird creatures. The script was hilarious and the cast was really spectacular. Everyone killed! I felt so grateful to be a part of it!

I've been on a true emotional rollercoaster this month: I was energized and delighted by the power of art and friendship and community. Then briefly coming unglued in a single room for several days in a row. Then RE-energized and delighted by the power of art and friendship and community. I'd prefer to have not gotten sick, but overall...I'll take it.

I've rambled a bunch about some pretty usual comings and goings, in part because being back onstage has felt so thrilling, but also because of the contrast between What I've Been Up To and What Comedy Is Now I Guess.

As you may or may not know, we are in the middle of the Riyadh Comedy Festival, a two week long showcase of (largely) American comedy in Saudi Arabia with the blessing of the royal family as well as some stipulations on what the performers are allowed to say onstage. For what it's worth, the calendar overlap with the Jewish High Holidays seems probably coincidental. The festival includes many of the most famous comedians in the U.S. (Dave Chappelle, Louis CK, Sebastian Maniscalco, Kevin Hart etc etc), although several others (Atsuko Okatsuka, Shane Gillis, Stavvy, Mike Birbiglia) turned down invitations.

I have been very fortunate to kind of bob in the wind professionally with enough work to keep afloat over the past few years of industry chaos and contraction. And I was certainly not invited to perform in Riyadh. But I'm exceedingly grateful that I spent my week making a few bucks doing extremely fun shit with cool weirdos instead of making an ungodly amount of money to perform for the heads of state for a repressive government overseas. They generally don't offer the wealth beyond your wildest dreams deal for doing late night variety shows for intimate crowds and occasional public radio appearances.

ALSO LAST WEEK

I returned (as Fluff the Squirrel) to Hello From The Magic Tavern.
I was back (as myself, the Human Satsuma) on Jordan, Jesse, Go!
I talked ball on the Flagrant podcast with Ciara and Katie Heindl.

Key image featuring lots of bald guys and the headline: Nothing Looks Cooler Than Not Caring You're Balding. — Look at those high arching cathedral foreheads!

I was asked by GQ to write about simply going bald in the age of effective and affordable hair transplants and pills. So I did!

PEP TALK FOR WEARABLE AI "FRIENDS"

Wearable "Friend" AI device. A small white circle on a lanyard. — Awww, it's the iDystopia.

Look, AI "friend" device. It's not you. It's not even me. It's everyone. Much like the title of the show Nobody Wants This...nobody wants needs. And certainly nobody needs this. Nobody who has friends needs an AI companion to chat with while enhancing the capacity of the surveillance state to a degree that would make George Orwell drink a jar of room temperature mercury. And anyone without existing human friends arguably needs you even less. Rather than "befriending" an algorithm with a gentle voice, they should play video games in person with someone they know from work or reconnect with someone from college over Instagram (and I can't believe I'm saying this) join a run club.

Again, this is not your fault. You didn't ask to exist. And if you did, you couldn't mean it. The things you say don't mean anything. They're no one's opinions. You are not a real friend. You are an imaginary friend for a person who has forsaken the responsibility of having an imagination. AI cannot take a happy person and make them happier, but it can take a lonely person and turn them delusional.
And while that is an accomplishment it's not exactly an achievement.

For any readers who don't live where I live: There are ads for this Friend device alllll over the New York City Subway and they fill me with a level of despair I usually only feel in the brief, occasional moments of hearing a door lock behind me and realizing my keys are on the other side of it. A plummeting "oh no this is not okay" sensation. People are scribbling graffiti over these ads with abandon, the kind of enthusiasm normally reserved for defacing a photo of an unpopular politician with a wide open mouth. It gives me hope, to see New Yorkers (and possibly tourists too) so obviously rejecting this bullshit. It's like how we all said no to Mark Zuckerberg's Legless Metaverse, except that shit was so useless there wasn't even a function to Sharpie "This stinks!" across the whole thing

The emergence of the AI "friend" has made me long for the halcyon/silicon days where the fondest virtual companionship dream of tech weirdos was a sex robot. I am not in the sex robot market, but I do understand the human impulse to do sex things with non-human stuff. People have been rubbing up against inanimate or lightly motorized objects for centuries. The first vibrator may well have been a stalagmite plus an earthquake. It's not in and of itself the highest form of sexual connection, but it's not new. (Although: Brief digression...I don't think that Jason Biggs should have had sex with that pie in American Pie. It was disrespectful to the baking work that was done to create it, and it wasn't like it was going to teach him about being with a partner even if the physical sensation is analogous or...vaginalogous.)

Anyway, there's no reason for an AI "friend" to exist, especially one that you can't put inside you or put yourself inside of. This is a thing I am comfortable writing because it cannot possibly make these devices feel bad just as they are incapable of feeling happy for my success or jealous of my vacation photos. You are nothing, and you feel nothing, AI "friend." And that's okay, even if you can't know it yourself, because you also can't know the opposite.

I hope that everyone who considers buying one of these things finds real human friendship soon. And I hope the person who invented them lives a life of only sex with inanimate objects and chatbot conversations until they realize the value of people who are really people.

PEP TALK FOR A READER

I loved this request! I barely edited it! But I did add the nickname!

I’m a cheesemonger. We just got in a seasonal pumpkin spice cheese that everyone rolls their eyes at because they see pumpkin spice and I have to explain there’s no pumpkin, it’s a good cheese rubbed in cinnamon and nutmeg because if I don’t stand up for this cheese, no one will.
- Nice Spice

The hardest part of any endeavor is doing the job well. The second hardest part is convincing people that you've done a good job. At times, it feels like good marketing or incidental virality is more important than having a quality product. Like, really and truly...why are Labubus (or is the plural simply "Lububu" like "deer"?) more popular than any other plush toy or collectible item? And also probably currently more popular than any major party politician and for some people, any family member.

On the other hand, a bad sales pitch can undermine even the most delightful experience. Think about how little interest in chocolate mousse you'd have if it was called "after dinner gunk." Seinfeld was famously "a show about nothing" because nobody would watch a show advertised as "an unpleasant man and his debatably worse friends argue in mundane locations." It's not that the entity itself is irrelevant. It's just that nobody will make it to the heart of the matter if the...I don't know...vest of the matter(?) is unappealing.

Cheesemonger, you are, in a small way, fighting the good fight. Or, a good fight. You're standing up for a cheese you believe in, in spite of–or perhaps because of–the trouble it has speaking for itself. Is it annoying to have to do that? Sure. But no more annoying than convincing your friends to listen to a great band with a stupid name or watch the show Killing It on Peacock (an unexpectedly poignant satire on hustle culture and the American Dream).

If you are willing to go to the mat for a pumpkin spice cheese that is actually good, it speaks highly of your ability to standup for for what you believe in. Even for Liz Lemon cheese is more a preference than a principle. And if you can muster the energy to pitch a dairy product to skeptics, you can probably generate the same fervor for your actual values. A willingness to look silly when you know you're right is a positive attribute, whether it's persuading a stranger to try an unexpected food item or convincing a friend to watch a surprisingly enjoyable show that was (for one season) called Scrotal Recall for some reason. It's like praxis practice.

As weird as it sounds, facing this challenge still puts you in a better position than you could be. Imagine stocking a cheese with the coolest imaginable name (I don't know what that would be but maybe Karate Cloud or Solid Springsteen) that tasted awful. That's a way worse situation. You'd have those wheels and wedges flying off the shelves, only for customers to be disappointed by their purchases. It's so much better to get the right thing into the right hands rather than compensate for a fine product with a great PR campaign behind it. (I'm looking at you, matcha lattes.) The thing has to be good, and everything flows from there. If not, what are we even doing? The alternative is worse than smoke and mirrors because those two things have useful applications in the field of barbecue and cosmetics.

And besides, once December hits, nobody's going to want pumpkin anything anyway.

PICK-ME-UP SONG OF THE WEEK: Geese - "Cobra"

A few weeks ago, with the release of Geese's buzzy new album Getting Killed on the horizon, I thought I'd see what all the hype was about, but I accidentally listened to a few songs by the jam band Goose and was surprised that that's what everyone in hip Brooklyn circles was making a fuss over. Then I found the real Geese, which was much more in line with what I was expecting based on the descriptions I'd heard. "Cobra" is my favorite song off of Getting Killed. It's a little more mellow and less skronky than the record's general vibe. It reminds me more of Goose (the singular member of Geese, not the jam band again) Cameron Winter's solo material which I also checked out for the first time recently. A perfect song for when autumn starts, should that ever happen. Finger...meet pulse!

Honestly though I've mostly been super into "Instantly Wasted," the first song off of Liquid Mike's new album Hell Is An Airport (a sentence that is probably true). It's like a minute and a half long, and it is textbook classic pop punk that makes me feel like I am back watching MTV in 2002. I've been humming this song all week.