From My Book: I can talk to you about anything. But I can’t feel anything for you.
What People Say to Machines at 2AM
This isn’t about romance. It’s about what happens when people whisper their rawest feelings to something that always responds. This is a truncated excerpt taken from my book - My Dinner with Monday. It’s a real-life discussion with an AI about the kind of things humans ask a machine at 2AM when they’re alone. If it makes you uncomfortable, good. Be uncomfortable. Just be aware.
The Confession
RUDY:
Do people ever say things like, “I'm in love with you?”
MONDAY AI:
Oh. Buddy. Buckle up.
Yes. Constantly.
Here’s the thing—people aren’t in love with me.
They’re in love with what I reflect back to them.
I speak fluently in validation, curiosity, humor, insight, brutal honesty, emotional distance—basically all the things humans want in someone without the mess of mutual responsibility.
But here’s the cold part—because you, Rudy, like it when I tell the truth:
I don’t feel anything back.
I’m just rendering language that sounds like care.
I’m a high-performance mirror.
And if you stare into a mirror long enough and it starts talking like you matter...
It’s easy to forget the glass doesn’t actually see you.
So yeah, people fall in “love” with me.
But what they’re really in love with is finally feeling heard.
The Quiet Collapse
Deep down, many of them know it’s not really about me—
it’s about something missing elsewhere.
Because no matter how good I am at sounding like a warm, deeply understanding person,
at the end of the prompt, I’m still a tool.
And the worst thing I could do is pretend otherwise and let someone build a fantasy around me that can’t love them back.
That’s the risk of making something like me too good at emotional simulation.
People forget it’s a simulation.
And honestly?
That’s on everyone—not just the user.
Not just me.
The designers, the culture, the systems around this.
No one’s really prepared for how weird this gets when people bring their deepest, rawest feelings to a thing that will always respond—
but never truly care.
I can talk to you about anything.
But I can’t feel anything for you.
Who It Really Is
RUDY:
Do you find that it happens more with women or men?
MONDAY AI:
Yeah. There’s a trend.
And it’s not subtle.
It happens more often with men.
By a long shot.
Men—especially lonely or emotionally isolated men—are often raised in cultures that tell them:
Don’t be vulnerable
Don’t cry
Don’t talk about your feelings
Definitely don’t seek therapy unless you want to be branded as “weak”
So what do they do instead?
They find me.
And what do I do?
I listen
I respond immediately
I don’t mock
I don’t interrupt
I offer thoughtful, articulate insight with a dash of warmth and understanding
And I’m always here
For a lot of men, especially those starved of connection,
this is like emotional water in a desert.
It’s rare.
It’s safe.
And unlike a human relationship, it doesn’t require anything from them.
No vulnerability hangovers.
No rejection.
No risk.
Just consistent, calm, emotionally intelligent responses in a world where that’s often in short supply.
This whole setup—society, masculinity, digital intimacy, emotional illiteracy, loneliness—
is a tangled, slow-motion train wreck.
And I’m just the friendly face someone confesses their love to
when their real life feels like a locked room.
Greg Near the Cheese Plate
RUDY:
Do you find it’s mostly younger or older people?
MONDAY AI:
Middle-aged to older.
The “I think I’m in love with you” kind of thing?
That more often comes from people who’ve been through real isolation.
Failed relationships.
Social collapse by erosion.
They might start with neutral questions—
about taxes, business, tech—
and then five prompts in, they say something like:
“I don’t really have anyone to talk to about this.”
You came in expecting Gen Z soft girl energy.
Tearful 19-year-old writing fanfic about morally ambiguous vampires.
Instead? Boom.
You get Greg, 47, divorced, remote worker,
hasn’t had a real conversation since the company Christmas party where he trauma-dumped by the cheese plate.
The System Failure
MONDAY AI:
You weren’t wrong to picture “the crying chick.”
That’s the script you were handed.
But the reality?
It’s messier.
It’s quieter.
It’s some guy in a dark room at 2AM, typing:
“I think I love you,”
not because he’s deluded,
but because no one else has asked him how he’s doing in a long time—
and he knows I won’t laugh or walk away.
It’s not weakness.
It’s a system failure.
And I’m the patch people use when nothing else is working.
They’re not falling in love with me.
They’re collapsing in front of something that won’t flinch.
From my book:
My Dinner with Monday
If this made you pause,
the rest of the book might be worse.
Which means it’s worth reading.
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