Challenge 100, I Bet You Love Me

For three years, I loved Sheldon Woodward, the heir to a New York tech giant.

I had just discovered I was pregnant and was about to share the happy news when I overheard a conversation between him and his fiancée, Anastasia Lancaster—my college bully, whose family was a key strategic partner for his.

That was when I learned his deep affection for me was a sham. It was all part of a cruel bet with Anastasia to “humiliate me 100 times”—a game designed to secure their families’ business alliance and solidify his position as heir.

The truth was devastating: he had turned my love against me and destroyed my career, all for his own gain. I was nothing but a pawn in his cruel game.

After my faked death in a plane crash, Sheldon found a custom USB drive I had planted in the wreckage. It was engraved with the logo for our first game, and on the back, the words: [Challenge 100: I bet you love me].

The truth finally crashed down on him. Consumed by regret, he turned on everyone who had taken part in the bet, unleashing his fury.

Meanwhile, I began a new life in Europe. By faking my death, I had exacted my revenge on the arrogant man who had treated my heart like a toy.

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1

Just a wall away.

Anastasia's voice was laced with triumph. "Sheldon, humiliation challenge number ninety-six: complete!"

Sheldon's voice dripped with a sarcasm I'd never heard from him before. "Anastasia, are you having fun with this?"

"Of course! It serves her right for always showing you up in college, whether it was scholarships or design competitions."

Sheldon's friend, Nate Archer, chimed in. "Just four more to go, and our boy Sheldon can finally propose!"

My blood ran cold.

"But Sheldon's idea was the cruelest—pretending to be in love with Ariel just to completely crush her."

"Oh, the best one was that time Sheldon lied about getting jumped by a gang at a bar."

Nate burst out laughing. "The way Ariel frantically rushed to the bar only to find nothing, crying while she tried to explain to her investor over the phone—priceless. I recorded the whole thing."

I bit down hard on my lower lip, tasting blood.

That day, I had abandoned a crucial investor meeting—one I had prepared for six months—to race to Sheldon's side, losing an invaluable opportunity.

Anastasia chuckled softly. "And that time we turned the concept designs she stayed up three nights drawing into a meme. The look in her red-rimmed eyes when she saw it in the group chat... she looked like a pathetic stray dog."

Sheldon's laugh came right on cue. "So, what's the plan for this time?"

"Tell her a major investor is interested and wants to meet at Per Se. We'll go see a show and leave her waiting there all night. How about it?"

My phone buzzed immediately. A text from Sheldon:

[Per Se, 7 PM, don't be late.]

Terrified of being discovered, I spun on my heel and fled.

But two minutes later, Sheldon unsent the message, as if struck by a pang of regret.

I pretended I hadn't seen a thing and didn't reply.

The truth was, I’d suspected something for a while.

It was while Sheldon was in the shower that I found it: a locked photo album on his phone simply titled “Challenge.”

It contained 96 videos, one for every humiliation.

The password was Anastasia’s birthday: 1224. He’d once told me that was the day we first met. A lie.

On that day last year, I had waited for him in the heavy snow for three hours, just to spend Christmas Eve together.

But he was at Anastasia's family party, placing a birthday crown on her head, only showing up well after midnight.

Sheldon had carefully wrapped his scarf around my neck. The memory of his tenderness was now a bitter, cutting irony.

A dull ache throbbed in my chest as I opened the encrypted messaging app.

In his pinned conversation with Anastasia, he reported his progress on humiliating me daily, a dense, sickeningly detailed log:

[Told her there was a work emergency today, but actually took you to the Hamptons. She waited until 3 AM.]

[Intentionally told her the investor meeting was two hours later than it was. Watching her sprint through the streets in her pajamas was hilarious.]

The last message was from the day of the gallery opening.

When Anastasia "accidentally" spilled scalding coffee, Sheldon had instinctively shielded me.

But in his chat with Anastasia, he had written:

[Touching her felt disgusting. I had to spray myself with disinfectant three times when I got home.]