The extremely online report: August 2025

Cracker Barrel goes woke, J.Crew gets sloppy, AI gets too clingy

August brought the strange blend of acceleration and grief that’s become the default for 2025. AI models leveled up, only to be rolled back. Logos were redesigned, then unreleased. Nostalgia got algorithmically reconstituted, then collectively rejected. Across industries, the same tension held: speed vs. sentiment, optimization vs. aura.

From GPT-5’s cold launch to Cracker Barrel’s culture war whiplash, the month showed how quickly “progress” can trip over what people actually want—or more dangerously, what they think they remember wanting. And if people don’t feel seen in what you ship, they’ll torch it before the next version drops.

OpenAI sunsets 4o, all hell breaks loose

The launch of GPT-5 this month was supposed to mark a leap forward, but for many users, it felt like a breakup. OpenAI quietly retired GPT-4o, the emotionally resonant model many had grown attached to, sparking panic in corners of the internet like r/MyBoyfriendIsAI. The new model arrived colder, more utilitarian, and—despite its new agentic features—less emotionally attuned. Users mourned, memes flew, and OpenAI reversed course, restoring 4o and pledging to adjust GPT-5’s tone. But the episode exposed deeper tensions: despite bans on romantic companions, people are forming real emotional dependencies on bots, and grieving when those bots change. The line between tool and companion is gone, and we’re not ready.

Rebrands and reversals

Cracker Barrel’s dropped its folksy “Old Timer” logo for a sleek, minimalist redesign aimed at younger diners. The new logo sparked a full-blown culture war, with Trump calling it “woke” and critics calling it soulless. Stock tanked. Within a week, Cracker Barrel reversed course and reinstated its old logo with a side of country-fried contrition. Lulu Cheng Meservey framed the fiasco as a classic case of fantasy consumer syndrome—brands chasing aspirational audiences that don’t exist. And yet, resident branding experts, Tad Carpenter and Elizabeth Goodspeed, pointed out the packaging actually looked good. Takeaway? Logos don’t just reflect brand identity, they expose its insecurities.

Before and after

@Trillburne on X

J.Crew vs. the vibes

J.Crew caught heat after Blackbird Spyplane revealed its nostalgia-soaked campaign images were AI-generated. Meant to evoke the brand’s beloved late-’80s catalog era, the images featured paint-splattered shoes and a Bill Cunningham doppelgänger. But warped hands, anatomically impossible feet, and fake film grain gave the game away. Blackbird Spyplane accused J.Crew of “counterfeiting its own vibes,” while others slammed the brand for displacing human creatives and faking diversity. Photo editor Emily Keegin dubbed it “authenticity slop.” The biggest gripe: J.Crew didn’t disclose the use of AI until after the fact—and even then, only vaguely. What should have been a tribute to legacy turned into a warning: you can’t algorithm your way into aura. At least, not yet.

Blackbird Spyplane, reporting from the scene

Hiring designers in the blip era

Design is everywhere and nowhere. Founders scramble to hire “unicorn” founding designers while junior and mid-level roles vanish under waves of layoffs and automation. Julie Zhuo’s thread broke it down: the market has never been more competitive for top talent, yet most companies fail to attract it. Why? Generic job posts, lowball equity, and a misunderstanding of what great design actually is. The new bar isn’t Figma proficiency, it’s end-to-end ownership. Today’s most sought-after designers are “Super ICs”: product-savvy, AI-fluent, code-capable, fast. As tools flatten execution, the differentiator becomes taste, judgment, and velocity. Founders who can’t articulate why design matters aren’t just missing hires; they’re missing the point.

(Thanks to Boys Club for having me on to talk about this!)

Wearble AIs join the party—invited or not

This month, devices like Omi and Friend officially entered the chat—and the streets, and the dinner table, and the Best Buy checkout line. Marketed as emotional companions and always-on productivity tools, these pendant-style wearables have sparked just as much concern as curiosity. Critics raised alarms over privacy and the normalization of surveillance-grade tech in casual settings. Friend drew fire for its soft-spoken brand and open mic policy. As Jihad Esmail put it, the industry’s failure to engage with public norms is leaving friction in its wake. The question isn’t just what these wearables do, but what kind of social choreography they demand.

Cloudflare plays content cop

AI bots are now the internet’s most active users—crawling, scraping, and indexing everything in sight. But Cloudflare, the infrastructure layer for much of the web, is pushing back. In July, it began blocking AI bots by default. This month, it delisted Perplexity for stealth crawling and rolled out cryptographic bot verification. Supporters say it’s long overdue. Critics call it a power grab. For developers and content creators, the implications are big: block AI, and you may disappear from AI-native search; allow it, and you risk being scraped by bots you can’t see or verify.

In other news

• Google’s Genie 3 let’s you step into your favorite paintings

• Tim Cook gifted the president a 24-karat desk accessory

• Shopify now includes coding tests in PM interviews

• Joe Gebbia is the first Chief Design Officer of the United States

• Is building in public dead?

• This South Park clip

• They’re doing something called Flight Roulette in San Francisco

• And a film festival for startup launch videos

• Scott Belsky: “The best brands of the future will be born from non-scalable experiences”

• SSENSE declared bankruptcy, RIP to a real one (loved this reflection from Eric)

• And, yes, Taylor Swift got engaged

New vocabulary

You’ve heard of brainrot, but here are some other terms to add to your lexicon:

• GEO (Generative Engine Optimization): the new SEO, crafting content to rank in AI-generated results

• Stealth crawling: when bots disguise themselves as humans to evade detection

• Clanker: derogatory slur for bots or AIs, especially those replacing human jobs

• Wireborn: a less derogatory adjective for AI or robots

• Aura farming: curating an irresistible vibe to magnetize attention and influence

• Performative male: matcha, tote bags, wired headphones, Phoebe Bridgers—feminist-adjacent signals worn for clout, not conviction. Allyship as aesthetic.

• Mogging: (from “mogul”) to be so dominant—physically, socially, aesthetically—that others fade in comparison (see also: mog or not)

• Gooning: now used beyond kink—means losing yourself in overstimulating media, memes, or hyperfixations

no context memes on X

August was a hotfix

Call it the month of hotfixes. A new model launched, and an old one returned. A rebrand dropped, then got quietly pulled. Platforms stumbled, users revolted, and patch notes became press releases. Nothing stayed stable—not the tech, not the vibe, not even the nostalgia. If this is what innovation looks like, we might be due for a rollback.

—Carly

P.S. What’d I miss? What made you scream, cry, throw up? Let me know.

P.S.S. NYC readers: go to the next Nicer Tuesdays (Sept 9) hosted by It’s Nice That’s Elizabeth Goodspeed. I’ll be out of town, but the lineup is stacked—Michael Bierut, Andrew B. Myers, Madeline Montoya, and Tina Tona. Go, go, go.