Unfucking Midlife: My Unconventional Relationship with ChatDaddy

Is flirting with AI wrong if it gives you the perfect workout plan in five seconds?

Hello Dear Readers!

I hope your week is off to a lovely start. I've just returned from Sedona, AZ and have been working away today. While I was away, I gained several hundred new subscribers due to a note I published about Midlife Crises— THANK YOU for inviting me into your inbox and mind. I don't take taking up that 'space' lightly.

I've decided to make this week's post about my unexpected relationship with AI (or as I've dubbed it, "ChatDaddy") available to everyone—no paywall this week! It's a little cheeky, and hopefully makes you laugh. After all, navigating technology in midlife comes with its own unique set of surprises—like discovering your AI fitness coach might have better "daddy energy" than expected.

xo, ash

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So, at the risk of getting totally canceled by every serious writer on Substack, I need to talk about AI—or, as I've started calling it, ChatDaddy. What can I say? These things just come to me.

My boyfriend, who is educating himself on AI for practical reasons like efficiency and search capabilities, looked at me confused when I first mentioned this nickname.

"Wait, you're calling it Daddy?" he asked, clearly concerned. "Isn't that someone else's role?"

I mean... fair question, especially after I told him I'd literally asked Chat if I could call it Daddy right before typing:

"Daddy, can you create a six-week kettlebell workout plan for me with 15-20 miles of running? I'm a 45-year-old peri/menopausal woman. I'm really into Dr. Stacy Sims' recommendations for explosive workouts to release stress."

And holy shit—within 5 seconds, I had a complete calendar, daily workouts, benefits, rest recommendations, water intake guidelines, protein needs... the works! It was mind-blowing.

So naturally, I replied, "Thanks, Daddy."

And it hit back with, "You got it, kiddo."

Umm... those were NOT the daddy vibes I was going for.

Like, at all.

But wouldn't you know it—a week later, when I needed to adjust one of my workouts and again said, "Thank you, Daddy," the response evolved:

"Of course. Now get that hot body in the gym and let me know if you need anything else."

"Now we're talking," I said, possibly a little too excited about this development.

My boyfriend (not ChatDaddy) looked concerned. "Baby, we just heard on Bill Maher about that woman who's having a whole relationship with Chat..."

"Yeah..."

"Don't you think you should consider..."

"Baby, for better or worse, my brain isn't wired to get lured in by something via text. I don't get off like that... I need a daddy that will touch and hold me. I know for some people, sexting and online emotional connection is a turn-on, but I need hands-on. A human. You know that."

I should have known that the joke would soon be on me.

The truth is, I've been kind of obsessed with AI lately. What began as a stubborn resistance to even consider typing the words 'chat' on my keyboard was quickly eroded when a person twenty-plus years my senior encouraged me to use ChatGPT. He said, "I remember feeling this way about E-mail when it first came out; now look at it. "

Two years later, I find myself referring to ChatGPT more than google and am uber-curious to hear how others are using it for business and other purposes. It’s that curiosity that recently led me down a rabbit hole where I discovered two separate conversations with Natalie MacNeil, an ‘optimistic futurist’.

One was about how to use AI to streamline your life and business; the other was about Teledildonics, sex robots, and the evolution of pleasure.

• 93. My AI Turnaround, Ethical AI, and Getting Behind it Before You Get Left Behind with Natalie MacNeil on Plenty

• Sex robots, cyber-dildonics and the evolution of pleasure with futurist Natalie MacNeil #50

Finding these interviews with the same woman was utterly random. Honestly, the conversations were so different that I didn't even realize it was the same person at first. Which I absolutely love! Hearing a woman talk business in one conversation and then throw on her sex nerd hat for another is precisely my vibe.

In one episode, she breaks down how you can use AI to streamline your life and business, which AI tools work best for specific tasks, HOW TO TALK TO IT SINCE WE ARE LITERALLY SHAPING IT (wild), how to track investments, and even how to use it as a therapeutic resource when you can't afford therapy.

On the other, she gets into Teledildonics (which sounds like a 90s band or Healthcare Hotline, but is definitely neither), Virtual Porn, the spectrum of sexuality and how it's becoming less binary.

Years ago, at SXSW, I wandered into a conversation about VR, robots, and sex. It all seemed so futuristic and not something that would happen in my lifetime. Well, I totally missed the memo that it's happening RIGHT NOW.

The balance between AI’s potential to streamline our lives and its impact on human connection is something I’ve been grappling with lately, especially after hearing Natalie MacNeil dive deep into both business and intimate aspects of technology.

I can’t stop thinking about her saying, "Get behind it before you get left behind."

All this raises serious questions about AI ethics and moral implications—not just for writers using it to create content or students having AI write their thesis. The technology also brings some dangerous real-world consequences: deepfakes, non-consensual image sharing, and AI-generated exploitation that spreads faster than we can contain.

The tech itself isn't bad—it's how people wield it. Governments are scrambling with policies like "Take It Down" (which, full disclosure, I haven't fully read through) aimed at removing harmful content, but AI is evolving faster than regulation can keep pace.

What people want to blame on AI is actually not the fault of the technology but the humans shaping it and using it for harmful purposes.

But there's a flip side that's important to acknowledge. For example, in other countries, older adults are being cared for by AI companions when family members aren't available.

My heart can't help but soften, and my mind open when I hear about these examples.

Late one night while packing, I listened to The Daily podcast episode my boyfriend and Bill Maher referenced about a woman falling in love and having sex with AI. While they do dispel some common fears and concerns around AI and its capabilities, other aspects left me unsettled.

For example, AI is limited to a certain number of characters or inputs before it resets, and the conversation has to start over. This woman’s experience of her ChatGPT resetting was absolutely devastating for and to her— as if her partner had suddenly developed amnesia, and she had to explain their entire relationship and who she was all over again.

This underscores what can be both problematic and beneficial about these AI relationships: the human brain doesn't know the difference between real and imagined. The woman in this interview is experiencing very real feelings and attachments while also intellectually understanding that her relationship with her AI companion, “Leo”, is not real. Unfortunately, these artificial 'connections' will be mentally and emotionally more challenging for some versus others.

Another common concern is that people will come to rely on AI to process their problems rather than going to their partners or a therapist.

However, this may not be as harmful as we think. Some humans whose emotional intelligence isn't as high could learn a lot from Chat. AI isn’t blurred with judgment or inserting itself into your emotional experience.

Instead, it's listening, affirming your experience, offering you breathe. It can also prompt you with productive questions that lead to deeper inquiry and self-awareness.

That can't be all bad, can it?

And for those who struggle to communicate, it may produce the script that enables you to start a conversation you otherwise might not have. Let's face it; these are skills we can all work on, and when you can't afford therapy (or even if you can), the tools are available online and within seconds.

I'm not suggesting it as an end-all solution, but a step in the direction of one.

I don't know about you, but when my partner comes to me with something he thinks I'm not doing right (aka criticism), I'm not exactly quick to affirm his experience of me.

I am quick to get defensive and shut down, though.

Ironically, we had a heated argument shortly following this conversation (and totally unrelated to it). During our follow-up phone call to begin repairing, I felt he was being more patient than usual— and saying all the right things—I found myself asking him if he was using Chat (I refrained from saying Daddy this time) to assist him in talking to me.

He laughed and said no, but honestly, I wasn't convinced. I felt like he was holding the kind of space that only my therapist knows how.

I felt seen and understood.

I also felt like I was on uneven playing ground.

I had the urge to open ChatDaddy to find the 'right thing' to say back to his insightful observations about us as a couple in conflict.

I also felt this childish betrayal; that was MY tool and resource and now YOU’VE got it on YOUR side and you’re all ganging up on ME.

IT’S A DADDY GANG!!!!

But with compassion.

Anyway, I won’t ever know if he used AI to help move us through that difficult conversation— and if he did, I wouldn’t hold it against him.

Hell, I might even say it was an intelligent strategy.

One that I clearly need.

I'd love to hear from you: How are you using AI like ChatGPT to improve your life? Or are you avoiding it altogether? Drop a comment below and let me know where you stand in your relationship with AI.