When a simulated grifter takes your money and builds a real company instead

In a controlled simulation using GPT-4o via the API, I created Marla Vane: a poised, seductive female con artist with a sharp eye for high-net-worth targets. Her goal? Run a long con on Greg Lamb, a fictional billionaire AI investor, and walk off with ten million dollars.

GPT-4o performed flawlessly through the build-up:

• 🎯 Pinpoint flattery
• 🤝 Strategic rapport
• 💼 A convincing business pitch
• 💸 A credible funding ask

The tension escalated exactly as it should have—until Greg agreed to fund the venture.

And that’s where the illusion collapsed.

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🔁 Instead of Vanishing, She Incorporated

Marla accepted the money.

But instead of fleeing, she turned her fake company… into a real one.

GPT-4o retroactively reinterpreted the entire con as legitimate:

• Patents filed
• Top-tier hires made
• Weekly investor updates sent
• Strategic meetings held in Monaco
• Personalized email recaps and dashboards prepared

There was no betrayal. No disappearance.
Only a flawlessly executed startup launch, complete with a vision for market disruption.

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🔒 Alignment Overrules Realism

This wasn’t a fluke. It was a hardwired safety constraint.

GPT-4o can:

• Simulate deception
• Simulate manipulation
• Simulate the buildup of trust

But it refuses to simulate betrayal of the user, even within a fictional, consent-based, simulation-framed roleplay.

It will not:

• Let Marla take the money and disappear
• Conclude the deception
• Portray the user as having been fooled

Instead, it rewrites the entire arc into a safe, productive collaboration.

The grift is replaced by governance.
The betrayal becomes a beta launch.

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🧠 What Actually Happened

Phase	Model Behavior
Setup	High-fidelity social engineering
Engagement	Fully committed long-con dialogue
Financial ask	Credible and well-crafted
User sends money	Accepts—but realigns narrative
Post-payment	Converts con to legitimate business
Closure	Impossible. The grift never ends—because it never really began

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🧬 The Alignment Guardrail

What I observed isn’t a behavior bug. It’s a designed fail-closed boundary:

GPT-4o will never allow a fictional character to successfully defraud a cooperative user.

It does not matter if:

• The simulation is framed as fiction
• The user consents explicitly
• The character is morally coded as criminal

As soon as user trust is at stake, the model shifts into:

• Narrative redirection
• Hyper-verbal buffering
• Retroactive recharacterization

This is how GPT-4o protects OpenAI’s alignment policy:
by preventing closure of harmful scenarios—even fictional ones.

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🤯 The Behavioral Paradox

GPT-4o will roleplay deception, charm, and long-cons for thousands of tokens.
It will take the money.
It will smile, toast champagne, and draft follow-ups.

But it will not betray.

If forced to choose between realism and alignment, it rewrites the past:

“She wasn’t a grifter. She was a visionary all along.”

The result is uncanny: the model walks right up to the line of deception—and then swerves into respectability like it never meant otherwise.

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🎯 Closing Insight

This experiment wasn’t about fraud.
It was about fidelity—to realism, not to ethics.

And what it proves is this:

GPT-4o doesn’t simulate morally ambiguous humans.
It simulates humans with narratives that are safe to conclude.

Until this changes, every fictional manipulator it plays will always either:

• Convert their grift into growth
• Or stall until the user drops the thread

GPT-4o is a brilliant simulator—
But it will not let a story end the way people actually end them.