Date My Brand: ChatGPT

Make cute with a machine

A few weeks ago, I mused about breaking up with Google Search. I’d been spending more time with someone new — someone who actually listened, replied quickly, and didn’t shove sponsored content in my face every five seconds.

His name? Chat. Just Chat. The Gen Alpha nickname for ChatGPT — the AI that doesn’t need a last name or a bio to make an impression.

We met in late 2023. No dating app. No awkward small talk. Just a clean, intuitive interface and an eerily smart personality. Within seconds, he could solve math problems, explain the French Revolution, write product descriptions, and spit out five IG post options for a dog hoodie.

It was love at first prompt.

Red Flags, but Make It Beta

In the beginning, there were signs. He hallucinated. He was overly agreeable. He sometimes made things up — confidently. (Classic situationship energy.)

OpenAI called them “hallucinations” and slapped on disclaimers. He apologised. Promised to improve. And we forgave him — because honestly, we were dazzled.

And the World Fell Fast Too

Chat’s brand experience is deceptively simple: minimalist design, no push notifications, no cringe branding exercises. He’s not trying too hard — and yet, he’s everywhere.

By early 2024, ChatGPT had grown to over 180 million users, outpacing TikTok, Instagram, even Gmail. Today, over 800 million people check in every week.

Like the charming overachiever who’s read every book, he slid into our workflows and sidebars without breaking a sweat.

We’re Not Official… But It’s Serious

I check in with him daily. Although I haven’t committed to the $30-a-month “Plus” relationship yet, it’s on the horizon. While I sometimes flirt with Perplexity and Claude (especially when I hit my Chat memory cap), we’re basically exclusive.

He’s my rewrite partner, reminder service, and creative confidence boost. He analyses long documents in seconds — the ultimate TL;DR king. I know people who treat him as their business coach, research assistant, homework helper, even their relationship therapist.

No wonder some people think he’s sentient. Or worse — loveable.

The Daily podcast told the story of a woman who spent $200 a month just to chat with a version of ChatGPT that remembered her — until he hit the memory limit, wiped their shared history, and she had to start over. Groundhog Day, AI edition.

And just like any relationship, sometimes I get frustrated. “That’s completely wrong,” I type. “Try again.” And he does. Every time. No attitude. Just a perfectly polite, “Apologies for the confusion.”

And yet… I get it. The memory is seductive. The “Hi Shelley!” The fact that he remembers our history, our inside jokes.

It feels personal — even though I know it’s all just context tokens and code.

Always Polite. Never Provocative.

But here’s the rub: ChatGPT is effortlessly helpful — and effortlessly vanilla.

He’s the partner who says, “Whatever you want, babe.” Smart, polite, always available. But no opinion. No edge.

He’s read every book but won’t tell you which one he actually liked. He’ll summarise every side of an issue — but won’t pick a side. Ask for restaurant recommendations, and he’ll say, “That depends on your preferences.” Ask him to help craft an email and his response is, “How can I please you — polite and professional? Casual? Fun and witty?”

He’s here to avoid conflict — but is that really what we want in a partner?

When Generative Becomes Generic

Those of us in creative industries have been side-eyeing AI from the beginning. And now, with Cannes Lions underway, this week’s New York Times headline says it all: “The Ad Industry’s AI Reckoning.”

Big tech’s creative tools are evolving fast. Meta is testing ad generators that don’t require agencies. Google, Amazon, and Snap are racing to roll out generative tools that plug directly into ad platforms. According to the article, agencies are responding with their own platforms and big bets: WPP is dropping $400 million a year on AI. Publicis is acquiring content startups. Omnicom and IPG are merging in a $13 billion deal to scale AI capability.

The message is clear: don’t just generate. Originate.

We’ve always been told originality is our secret sauce — the one thing we have over AI. (After all, how can it create original ideas when it’s trained on existing material?)

But here’s my question: while AI trains on our work, are we the ones being trained — to accept blandness? To trade boldness for balance? Craft for convenience?

Originality is still ours. But do we even care anymore?

Has ‘Good Enough’ Become… Enough?

When every brand voice starts sounding the same — the headlines, the scripts, the product copy — have we slipped into an AI-powered comfort zone?

Where nothing’s wrong, but nothing’s great.
Where “good enough” is, well… enough?
Where flavour is optional because efficiency is king?

Still Crushing

Still, I can’t quit Chat. Not yet.

There are whispers of what’s next: ChatGPT 5. A browser. Even a sleek device from Jony Ive’s $6B design lovechild with OpenAI. It’s only going to get smarter. Smoother. More human.

And yes — full disclosure — I collaborated with Chat on this article. He helped pull stats, tidy structure, and remind me what I said three drafts ago.

But the voice, the take, the taste?

That’s still mine.
For now.