Charles Bass is a brilliant businessman, a playboy billionaire…and a jewel thief? Insurance investigator Blair Waldorf is determined to get her man before he pulls off his most daring caper yet: stealing her heart. Inspired by The Thomas Crown Affair film.

Therapists weren't supposed to have favorite clients, but Dr. Isabelle Cerra was only human.

When she'd seen the name "Charles Bass" in the 3 o'clock slot on her patient schedule for the day, her lips had curved into a subtle smile. Now, sitting across from him, that smile had been subdued and she was all business.

"Do you still feel as though you are suffering from ennui, Mr. Bass?"

The gentleman in question shrugged.

Ah, he was going to make this difficult. A session with him was bit like playing a game of chess: one had to focus on the current move and also anticipate several moves ahead. While mentally stimulating, it could also border on the frustrating.

"You realize this is most unlikely from a man in your position?"

"In my position?" He did appear curious at that, and she was taking it as a minor victory.

"Yes, you're young and you're healthy." He was about thirty years of age, toned and fit but without the look of someone obsessed with those goals.

"Most would consider you physically attractive." He had a jawline that might've been sharpened on a whetstone, a strong chin, high cheekbones and a proud forehead. The most startling features, however, were his eyes – a mysterious color that was a kaleidoscope of shades from amber to bronze to mocha. They were set at an exotic slant in his face and accented by bold, dark brows that seemed to express as much as the eyes themselves.

Right now, the brows were raised in surprise. "Only most? You wound me, Dr. Cerra." His voice was deep and he knew exactly how to use it to charm and persuade.

"You're well dressed," she continued, undeterred.

He did smile a bit at that, as he was rather proud of his reputation as an international trendsetter in men's fashion. He never looked less than his best, often wearing styles and color that would appear clownish on another man.

"Intelligent, successful."

"Define 'success'."

She gestured out the window. "How much of Manhattan do you own, Charles?"

"Not enough," came the swift reply.

"A substantial chunk of it, if gossip is to be believed."

"Oh, come now, Dr. Cerra, please tell me you don't believe the fiction that passes for gossip?"

"What about the Wall Street Journal? The Forbes 500? Should I doubt those sources? They all classify you as a financial wizard who's greatly multiplied the empire his father left him."

He snorted. "No one would be more surprised by that than him."

"The front page of today's New York Times says you've just pulled off another successful merger. You don't feel he'd be proud of that? Proud of you?"

"I think the only thing Bart Bass was ever proud of was himself. He found the rest of the world…disappointing."

She frowned. "But how do you see yourself? Are you satisfied with your achievements?"

"Satisfaction is…an elusive concept."

"Complete satisfaction, yes, but there should be a certain degree of restlessness in one's life to encourage one to reach for more, to try new things. It's how I came into my career."

"And what did you do before?" It was something he had always wondered about her.

"I was a high school teacher. And I loved it, don't get me wrong. But I found I loved the students and talking with them about their lives was far more fulfilling than standardized tests and lesson plans and the like. I think the human psyche is fascinating."

"Do you?" The brows went up again.

"Don't you?" she countered.

"I find most people and situations all too predictable," he frowned.

"You feel…unchallenged?"

"I feel there's something missing."

"Maybe it's intimacy, a woman?" She dared to bring it up.

"Only one woman?" he chuckled. "Women aren't intimacy." He sounded confident of that. "They're…entertainment."

"I'm sure you've found a number of them entertaining. Have you ever been in love?"

He outright laughed at the idea. "That's for poets and songwriters and schoolchildren."

"Do you feel it's possible you could meet someone who is your equal, a partner? Someone you could trust who trusts you? Someone who makes you happy?"

He grew serious then. "If life has taught me anything, it's that happiness doesn't seem to be on the menu."

If it were any other patient, Dr. Cerra would encourage them to take steps to reclaim their power over their life, but none of them was the enigmatic playboy billionaire sitting in front of her. There was something heartbreakingly tragic about a lost man in his prime, who had the whole world at his feet and yet felt empty. No, control was not Charles Bass's problem; what he needed was someone or something to make him lose that control. And finding that, unfortunately, was a matter of timing and luck.

When her client had left and she was alone again, she picked up her newspaper from earlier in the day. The story below the fold detailed the latest merger acquisition of Bass Industries and its effect on the Bass empire. Isabelle flipped the paper over to see what could possibly top the business coup.

The lead story was a jewel heist, one of the biggest ever, from a special exhibit at the Metropolitan Museum of Art. A flawless diamond of unusual size called The Empress had vanished. The article went on to detail that New York police were investigating and the company who had insured the pendant was sending a recovery specialist to aid in the search. They were optimistic that the necklace could be recovered, or certainly very hopeful they could avoid a one hundred million dollar payout. The main stone in the necklace, The Empress, was said to be a lucky gem, and whoever had taken it would need luck indeed to avoid capture.

Possibly as much luck as Charles Bass needed to find what was missing in his charmed life.

To Be Continued in Chapter 2

Author's Note

Welcome to my new story, y'all! The Thomas Crown Affair (the 1999 version with Pierce Brosnan and Rene Russo) is one of my all-time favorite films. Who can resist a good heist film combined with a love story? It's all about the chase. Will love win out? We shall see.

The chapters in this story will be shorter than my usual length, or, as Almaloney33 said, "fun size, yeah, baby!"

I hope this installment brought a smile to your face. As always, I love to hear from my readers, so don't be shy with the review button. I like knowing that people out there still love Chuck and Blair like I do.

Special thanks to Chrys1130, Almaloney33 and Shrk22 (sly wink).