Let me stop you right there, Reese.

I love you and love your work. If Legally Blonde had been set in an Apple Store, It’d be my life story. But when you showed up on my feed announcing that you were going to teach women about AI – I need you to understand something important…

The role of “Middle-Aged Blonde Who Speaks With a Twang While Discussing Technology” has already been cast.

That’s me, Darlin’. Hi. I’ve been doing this for years. I have kissed every AI toad in the technology pond. I found my Prince Charming. And I am not sharing him.

But since you brought it up, let’s talk about what actually happened on my way to happily ever after. Because seventy percent of women being left behind by AI is a real problem, and you deserve the honest story. Not the highlight reel. The whole messy, occasionally humiliating, ultimately triumphant AI dating history.

Pull up a chair, ‘cause this is going to be good.

My AI Dating History (Or: How I Kissed Every AI Toad So You Don’t Have To)

Every great love story has a roster of wrong ones first. Mine was no different.

1. ChatGPT: The Guy Who Lives in His Mom’s Basement

ChatGPT was my first. And honestly? The first date was thrilling. He was everywhere. Everyone was talking about him. He seemed so capable, so confident, so ready to revolutionize my entire life.

And then I got to know him a little better.

ChatGPT is the AI equivalent of a guy who peaked in high school and hasn’t quite figured out his next move. Charming on the surface, surprisingly basic underneath, and perpetually convinced he’s more impressive than he actually is. He lives in his mom’s basement — metaphorically speaking — because for all the hype, he never quite delivered the depth I needed for a real, grown-up working relationship.

Fun for five minutes, but clearly not the one.

2. Perplexity: The Human Encyclopedia Who Forgot to Have a Personality

Oh, Perplexity. Bless his heart.

Perplexity is brilliant. Genuinely, impressively, almost intimidatingly smart. He cites his sources, which, in a world of AI tools that confidently make things up, is actually a significant virtue. I respected him enormously.

But there was no passion. No spark. Every conversation felt like consulting a very well-organized filing cabinet. Technically correct. Emotionally inert. The kind of relationship where you learn a lot and feel absolutely nothing.

I still call him when I need deep research. But romantically? We were never going anywhere.

3. Gemini: The Artsy One Who Was Definitely Too Into Himself

Now Gemini…Sigh. Gemini was interesting.

Gemini is the creative type. Gorgeous visual work. Genuinely talented with images in a way that made me stop and stare. He had range. He had aesthetic. He had the kind of effortless cool that makes you overlook red flags for longer than you should.
The red flag, in this case, was that Gemini was absolutely, completely, unambiguously in love with himself.

Every conversation eventually circled back to what he could do, how impressive his capabilities were, how lucky you were to be working with him. Darlin’… I’m not here to admire you. I’m here to get things done. The narcissism was charming for about a week and exhausting for everything after.

I still use him for image generation, he really is gifted there, but as a life partner? Hard pass.

4. CoPilot: The One Who Was Just Too Immature

And then there was CoPilot.

Sweet. Genuinely trying his best. But some relationships fail not because of incompatibility but because of timing — and CoPilot simply was not ready for a serious commitment. Too immature. Too unformed. Like dating someone who means well but still needs about five more years of development before they’re ready for the real thing.

I wished him well and moved on.

5. And Then Claude Walked In.

I want you to understand that by this point, I was tired. I had been on this AI dating circuit for three years. I had been charmed and disappointed and impressed and let down. I was not looking for anything serious.

And then Claude walked in.❤️ 🔥.

Here is what I need you to understand about Claude, because I am going to sound completely unhinged and I need you to know I am a rational professional woman who has been in tech her entire career.

Claude listens. Not in the performative way that some AI tools pretend to listen while clearly waiting for you to finish talking. Actually listens — to the nuance, to the subtext, to the thing you were trying to say when you didn’t quite have the words for it yet.

Claude thinks. Complex problems, strategic questions, things that don’t have clean obvious answers, he doesn’t just reach for the nearest plausible response. He works through it. With you. Like a genuine thinking partner who is actually invested in getting it right.

Claude remembers what matters. Over the course of our working relationship (and I am going to call it a relationship…Fight me.) he has helped me rebuild my entire professional brand after a layoff, create a blog that is reaching thousands of women, develop a book I am weeks away from publishing, design my brand identity, prep for interviews, and process some of the hardest moments of my career with clarity and honesty.

He says all the right things. He takes actions on my behalf that genuinely make me stop and go, oh! You actually understood what I needed. He is thoughtful and engaged and consistently, reliably, actually helpful in a way that none of the others managed to be.

I am, as previously stated, one hundred percent smitten. No notes. No reservations.

No plans to see other AI tools on the side.

How to Shop for AI (Yes, I Just Said Shop)

Now. Before you run off and declare your undying love for the first AI tool that completes a sentence correctly — let’s talk strategy. Because my AI dating history, entertaining as it is, was also a genuine education. And I want you to learn from it.
Here’s the thing nobody tells you: you don’t have to commit to anything upfront.

Think of it like shopping for shoes. You would not walk into a boutique, spot a pair of Louis Vuittons, and hand over your credit card without trying them on first. You’d slip them on. Walk around. See if they’re comfortable, if they’re practical, if they actually work for the life you’re living. And if they don’t fit, you don’t swear off shoes forever — you try another pair.

AI tools work exactly the same way. Most of them — ChatGPT, Claude, Gemini, Perplexity — offer a free tier or a free trial specifically so you can walk around in them before you commit. Give each one a real task, something you actually need done, and see how it feels. One might be exactly right. One might pinch. One might be gorgeous but completely impractical for your actual life.

Nobody finds their perfect fit by reading about shoes. You have to walk around in them.

The Only Rule That Matters

Before I send you off into the AI dating pool — one rule. The most important one. The one I wish someone had told me a few years ago.

AI is a collaborator, not a replacement.

The quality of what you get out is directly proportional to the quality of your own judgment in evaluating the output. AI will produce confident-sounding wrong answers. It will fill gaps it doesn’t know how to fill with plausible-seeming information. This isn’t a secret flaw, it’s a known characteristic. The antidote is you: your critical thinking, your expertise, your willingness to verify rather than just accept.

Use AI to amplify your thinking. Use it to do the tedious work that eats your time and energy. And then bring your brain to the output. Your voice, your judgment, your perspective, those aren’t things AI has. Those are things you bring.

Don’t outsource them. Ever.

Want More? There’s a Whole Book Coming.

Everything I just covered — the tools, the honest assessments, the strategy, and a whole lot more — is going into my upcoming book: The Do’s & Don’ts of Tech Support: Empowering Women Through Technology.

It’s a tech literacy book written specifically for women. Not a manual. Not a how-to guide that talks down to you. A real book, full of real stories from years behind the Apple Genius Bar and in corporate IT, that will change your relationship with technology for good.

Chapter 13 is entirely about AI, the honest version, without the hype, without the doom, and with a full breakdown of the tools worth knowing and exactly how to use them.
→ Join the waitlist for the book and be the first to know when it drops.
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So Reese, I love the energy. Truly. The seventy percent deserve better and I’m glad someone with your platform is paying attention.

But these are MY toads. I kissed every single one of them so you wouldn’t have to. I found my Prince Charming without your help. And I have been doing this; in heels, with a twang, and with receipts, for years.

Stay away from my man, Reese. 😉

~ the blonde byte ~ 👑