My mom called me three times last Tuesday. The first was to ask how to “log into the ChatGPT.” The second, twenty minutes later, was to report that “it’s broken.” The third call came an hour after that—she wanted to know if I’d seen the poem it wrote about our dog.

Watching boomers discover ChatGPT has become its own genre of family entertainment. Only 20% of baby boomers use AI weekly, compared to 70% of Gen Z, but when they do finally try it? It’s a journey. Not the smooth, intuitive kind you see in Apple commercials, but something more entertaining—equal parts confusion, wonder, and the absolute certainty that they’re doing it wrong.

1. The search engine approach

They type into ChatGPT exactly like they’re Googling something. “Weather today.” “Best restaurants near me.” “How to remove red wine stain.”

Older generations treat AI as an advanced search engine, which makes sense—they spent decades training themselves to communicate with technology through keywords. Now you’re telling them the robot wants full sentences? Politeness? Context?

My dad’s first ChatGPT query was literally “Italian restaurant.” Not a question. Not a request. Just those two words, sitting there like he’d dropped them into a suggestion box and walked away.

2. The over-explanation phase

Once they realize ChatGPT responds to conversation, the pendulum swings hard in the other direction. Suddenly they’re writing novellas.

“Dear ChatGPT, I hope this message finds you well. I am writing to inquire about Italian restaurants in my area. I live in Portland, Oregon—not Portland, Maine, there are two of them you see—and I’m looking for something nice but not too expensive because we’re on a fixed income since retiring…”

They’re providing their medical history to ask about pasta recommendations. About half of ChatGPT usage involves “asking”—treating it as an advisor rather than a task-completion tool—but boomers take this further. They’re not just asking; they’re establishing rapport. Offering their life story as credentials.

3. The suspicion

Right around message three, doubt creeps in. It’s working too well. The responses are too helpful, too immediate, too knowledgeable.

“How does it know all this?” my mom asked, squinting at the screen like ChatGPT might be reading her emails. “Is someone typing this? Is this a person in India?”

There’s real distrust of anything that seems magical—they lived through enough “revolutionary” technologies that turned out to be garbage. The suspicion phase involves testing, asking the same question different ways, trying to catch it in a contradiction. They’re doing quality assurance like they’re about to write a Consumer Reports review.

4. The excessive courtesy

Once they accept it’s real, they become extremely polite. Aggressively polite. “Please,” “thank you,” “if it’s not too much trouble” appear in every message.

I watched my uncle type “Thank you so much for your help” after ChatGPT explained how to reset his router. Then he added, “I really appreciate your patience with me.” He was genuinely worried about being rude to the algorithm.

This isn’t just quirky—it’s kind of lovely. Nearly half of boomers who use AI say they’d use it more if it were integrated into familiar technology. The courtesy is their way of bridging that gap, treating new technology with the same social contract they apply to everything else.

5. The evangelical phase

After three successful interactions, they’re convinced they’ve discovered fire.

“You HAVE to try this,” my mom told me about ChatGPT. I’d literally sent her the link. I’d walked her through setting it up. But now she was forwarding me ChatGPT’s recipe for lemon bars like she’d unearthed a Dead Sea Scroll.

They start using it for everything. Grocery lists. Greeting card messages. Explaining the plot of “Succession” because they fell asleep during season two. Younger users increasingly rely on memory-enabled ChatGPT for major life decisions, but boomers are out here asking it to settle decades-old arguments about whether “irregardless” is a word.

6. The oversharing

Somewhere between wonder and dependency, they forget they’re talking to an AI and start treating it like a therapist.

My friend’s dad asked ChatGPT to help him write a sympathy card, then spent 45 minutes telling it about his own father’s death in 1987, his complicated feelings about funerals, and whether he should mention the casserole he’s bringing.

The AI doesn’t judge, doesn’t interrupt, and apparently that’s exactly what some people need. It’s weirdly wholesome until you remember every conversation potentially becomes training data.

7. The feature creep

Final stage: they discover capabilities you didn’t know existed because they’re clicking every button, trying every feature, absolutely refusing to just use the basic chat function like a normal person.

My mom somehow got ChatGPT to generate a meal plan, cross-referenced it with her grocery store’s weekly circular, then had it write a complaint email to said grocery store about their produce quality. She’s using it like a personal assistant, life coach, and consumer advocacy service rolled into one.

Three-quarters of ChatGPT conversations focus on practical guidance, seeking information, and writing, but boomers have cracked some kind of code. They’re not bounded by how it’s “supposed” to work—they’re just asking it to do stuff and seeing what happens.

Final thoughts

Watching boomers learn ChatGPT is like watching someone taste tomatoes for the first time and immediately start planning a garden. There’s no chill, no playing it cool. Just pure, unfiltered reaction—skepticism to wonder to dependency at speeds that would make adoption specialists’ heads spin.

Maybe that’s what happens when you’ve spent your life being told technology would make things easier, then watched it consistently make things harder. The technology that actually delivers feels like magic, even when you’re pretty sure it’s also stealing your data.

My mom’s latest ChatGPT project? Having it write a letter to her local representative about crosswalk timing. She’s treating artificial intelligence like a very patient intern who happens to work 24/7 and never judges her for not understanding cryptocurrency.

And honestly? That might be the healthiest relationship with AI any of us have figured out yet.

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