The Best Trade

Fiction Romance

Written in response to: "Write about a character who can’t stop checking something." as part of What Keeps You Up at Night.

It began when Dillon’s Grandpa gave him a thousand dollars for his eighteenth birthday. Dillon immediately opened a Robinhood investing account. A wise move for such a young man. However, it quickly became a huge problem.

His friends first noticed Dillon constantly checking his stock's performance. Then he began obsessively talking about them, anxiously trying to decide whether to sell or hold them. The turmoil inside Dillon rose to an unhealthy level. He couldn’t stop checking his Robinhood app.

Clara decided to intervene. Friends since grade school, she knew him best and cared the most.

“The season opener is tomorrow. You coming over?” Clara asked.

Dillon nodded.

“I only ask one thing,” Clara said. “No checking your app. Let’s…watch…the game. Got it?”

“I will, as soon as the after-market ends.”

“No! No after-market.”

“No after-market? Are you crazy? The biggest swings happen after hours.”

“You’ll live. I mean it. No checking at all. You need a break.”

“You sound like the guys. I need a break as much as the Chiefs need a better quarterback.”

“Funny. But I’m serious. You need help. For just one night, live in the real world.”

“We’ll see.”

The next night, Clara watched her beloved Chiefs win while her beloved friend lost. He never stopped checking. As a matter of fact, Dillon sunk even deeper into the world of investing after gaining fifteen percent in only four months.

High school graduation came and went, leading them both to the same university to major in accounting. Through freshman, sophomore, and junior year, Dillon remained glued to his screen. Even in their senior year, when Clara suddenly started wearing hats to class every day, Dillon was too absorbed in market trends to even ask why.

“You ready for Mr. Frimmer’s killer final? We should have studied together,” Clara said as she slid into a chair next to Dillon.

“You know, busy, busy, busy.”

“Yeah, I know, stocks, stocks, stocks.”

“You know me so well,” Dillon laughed. “I could use your help in Auditing and Attestation. I suck at it.”

“Um, well,” Clara stuttered. “I would if I could, but I have a thing I have to do tomorrow and I already took the final.”

“How? Frimmer is a butthole.”

“Not with everything.”

“Whatever, I’ll get Adam to help.”

Dillon’s self-absorption stung Clara, but she hid it well. She was very good at hiding things from him, although it wasn’t difficult.

The next day, Adam and Dillon crammed for Frimmer’s final, feeling out of their league. They both sucked at Auditing and Attestation.

“No, that’s not it, not even close,” Adam said.

Dillon smothered himself with his pillow while lying down on his bed.

“Just kill me now. I’m never going to pass this. What was Clara thinking? She knows we suck.”

“Give her a break, man. She’s got more than tests to fight right now. You know?” Adam looked at Dillon and shook his head in astonishment while Dillon stared at his phone, tapping the screen. “Seriously, man!”

“Sorry, things just got real. The S&P 500 fell two points.” Dillon frantically tapped his phone. His eyes widened, and his anxiety level rose way more than two points.

“You loser! Don’t you even care? Clara needs all the support she can get.”

“What are you talking about? She already took the test.”

“You know that’s not what I’m talking about.”

“Then what are you talking about?”

“Are you going to make me say it? You know Clara would die if she heard me say it.”

Dillon lowered his phone and stared at Adam. “Say what?”

Adam closed the dorm room door and whispered, “Cancer.”

Dillon’s phone fell along with his jaw and his spirit. He picked up his phone and saw a crack going from top to bottom, splitting his screen in two and distorting his S&P 500 chart. In this moment, he realized Clara meant more to him than two points.

“I figured it out a few weeks ago, but you know Clara. She’s the most private person I’ve ever known,” Adam said.

“Wait... how could you possibly know that?”

“I don’t split my attention.”

Dillon drove to University Hospital, not knowing if Clara was there. He raced to the front desk.

“Are you family?” A kind elderly woman asked.

“Her brother,” Dillon said.

She smiled sympathetically and pointed to a map of the hospital indicating Clara's location.

He made it in time to see two nurses wheeling Clara in a bed to a private room. He lightly knocked on the open door and one of the two nurses asked who he was.

“Her brother.”

The nurse looked down at Clara, who nodded. “He’s a butthole, but still my brother.”

The nurses left.

“Who told you?” Clara couldn’t raise her voice or her temper. The radiation drained her energy.

“Adam.”

“I knew he’d be difficult. He notices too much.”

“Well, didn’t you think I’d notice?”

“No,” Clara smiled, pulling back her punch.

“Ouch.”

“I know you don’t mean to be so unobservant. Don’t worry. I’m used to competing with Robinhood."

Hot tears filled his eyes. He blinked, trying to hide them. He saw her bald head reflecting the lamplight. The hats made sense now. He never asked why she started wearing them—too busy asking why the market turned. He remembered his cracked phone. Suddenly, a fierce rage took over. He wanted to shatter the cursed thing into a million pieces. It stole so much, demanding everything from him. He refocused on her head again.

“Don’t look,” Clara covered her head with both hands. “It’s hideous.”

“The only hideous thing in this room is me.”

Clara searched Dillon’s eyes, not sure where this came from.

“Why did you put up with me? I only focused on gaining points, so wrapped up in charts that I never saw you. I knew the market was sick, but I didn’t know you were.”

Hot tears flowed unbidden. Charts filled his mind. They sprouted hands and grabbed Clara, trying to drag her from his sight. He shook the thought from himself. No more.

“Forgive me,” Dillon said.

Clara teared up. She smiled through her tears and said, “I've always been an invest-and-hold kind of girl.”

He stayed with Clara until a nurse kicked him out. After that night, he asked Adam to sell every stock and cancel his account. He didn’t quit investing; he just moved all his capital into Clara, and never sold. Years later, he’d tell people it was the best trade he ever made.

Posted Sep 19, 2026
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13 likes 9 comments

Heather Rogers
September 20, 2026 13:35

This is s sweet story. I guess I’m an invest-and-hold kind of girl too. Otherwise, you would drive me crazy when and the Robinhood talk! 🤣 Love you, babe!

Reply

Daniel Rogers
September 23, 2026 02:41

I'm glad you are. Love you too

Reply

Marjolein Greebe
September 19, 2026 12:59

I loved how the investing metaphor carried all the way through to the ending. “I’ve always been an invest-and-hold kind of girl” was a lovely line, and the final “best trade” landed perfectly.

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Daniel Rogers
September 23, 2026 02:45

I'm happy you enjoyed those lines, I didn't find them until the third or fourth draft.

Reply

Marjolein Greebe
September 23, 2026 18:44

Yeah, sometimes the best sentence doesn’t show up until a later — or even the final — version. Funny, isn’t it?

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The Old Izbushka
September 23, 2026 15:21

Loved the ending!! The most important asset we will ever have is the people who love us. So happy he finally saw what was truly worth investing in!! Great story.

Reply

Daniel Rogers
September 27, 2026 00:15

Well said 😀 You couldn't be more correct. Our loved ones are our greatest investment.

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Red Herring
September 22, 2026 02:07

Well done weaving a reality check into the obsessive checking prompt, smart take. Definitely tugged at the heart strings. Great last lines too!

Reply

Daniel Rogers
September 23, 2026 02:40

Thank you 😀

Reply

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