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Naomi Blackwood: Toronto’s Most Intriguing Evening

The First Encounter: A Collision at the St. Regis Bar

The clink of crystal glasses filled the St. Regis Bar when our worlds collided—literally.

Him: Spilled Macallan M whiskey soaking into his Tom Ford suit.
Me: Steady hands catching the falling glass before it shattered.

“Those cost more than your watch,” I remarked, setting the glass upright.

*Private equity. Mid-50s. The kind of man who hadn’t been challenged in years.* His eyes flashed—first anger, then intrigue.

“Naomi Blackwood,” I extended my untouched martini. “Let me replace that drink… and perhaps your evening.”


The Crisis: 

Dinner at Canoe took an unexpected turn when his phone erupted.

I watched his facade crack—just for a second. Most companions would offer empty comfort. I pulled out my phone.

Four calls later: The sketch was safely stored under his daughter’s name at a private Zurich vault.

“How the hell—?”

“You mentioned her art history thesis last week,” I sipped my Château d’Yquem. “Sentimentality always leaves traces.”

His exhale of relief was more intoxicating than the wine.


The Midnight Walk: Truths by the Waterfront

Later, along the darkened Harbourfront, he asked the inevitable:

“Why does someone like you do this?”

The lake wind carried my answer:

“Because kings and CEOs all want the same thing—one person who doesn’t want anything from them.”

For the first time all night, he had no reply.


The Penthouse Dawn: Where Time Stopped

What began as dinner became:

  • 4 AM piano duet (his surprisingly deft Chopin)

  • An accidental solution to his Singapore merger deadlock

  • That electric moment when professionalism almost slipped

As sunrise gilded the CN Tower, we stood in silence. This is real luxury—**not the price tags, but the priceless moments between them.*


The Morning After: A Note on Montblanc Paper

Left on the Steinway:

“N—
For the first time in a decade, I didn’t check my phone for 8 hours.
Until Monaco. —E”

I tucked the note into my Hermès KellyAnother perfect night archived.

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