If the Shoe Fits

Courtney Dailey

I’m confronting him. Tonight. I just need to muster a little courage first. 

The building is dark. My feet ache, but I’m taking my time anyway, carefully vacuuming every inch of these office cubicles while saving my favorite office for last. His office. 

I glance down the dark hallway where his door stands ajar, a yellow rectangle of light spilling onto the carpet. We’re always the last two here. Always. Does he do that on purpose?

I run my sweaty palms down my pant legs. He’s the reason I come in 45 minutes early to clean. It’s his smile and the sincere encouragement he pours on my parched self-esteem.

Charles Prince may be the COO of this company, but he certainly doesn’t act like it. He doesn’t just see numbers and profits. He sees people.

He sees me.

My first night working here three months ago, I was a nervous wreck. Yes, I’m an entrepreneur and yes, I’m my own boss. But it’s still unnerving taking on new clients. Especially big ones like Prince Financials.

I was a clumsy mess that night. I carelessly bumped the vacuum into a plant stand and it crashed, sending potting soil five feet in every direction. I scrambled to clean up the dirt, certain I would be fired. Then I’d startled when I heard his voice. 

Charles Prince, in the flesh. Standing over me.

“I can’t thank you enough.” He grinned when I looked up. “That was the ugliest plant I’ve ever seen. About time someone put it out of its misery.” His eyes sparkled with amusement. 

That night was the beginning. Now Charles visits with me every night I clean here. He stays late and walks me to my car, claiming the downtown district is too dangerous for a lady walking alone. If he’s only concerned for my safety, why all the personal questions about my Cindy-rella Cleaning Service, single mom life, and the toys my kindergartener likes?

That’s what I’m figuring out. Tonight. My stomach is in knots.

The last few weeks, Amazon has delivered anonymous packages to my door every few days. First, it was a box of our favorite snacks. Then a monster truck for my son. But yesterday tipped the scales. I opened a pair of $150 Nike tennis shoes. Just my size. And I’d recently mentioned to Charles about my feet hurting… 

Suddenly my chores are done. No more stalling. I take a deep breath and head for Charles’ office door. I glance down at the box of Nikes with the envelope on top. I must be losing my mind. Why did I decide this was a good idea?

I mean, realistically. What are the odds a guy like Charles Prince would be interested in the cleaning lady? This might be social suicide.

I’m three steps from his door when I stop. Charles is on the phone.

“You always make me laugh, Olivia. I love you,” he says, affection echoing through the open door. 

His words yank the floor out from under me. I cover my mouth. Olivia? He’s with someone? Well of course he is! Why would I assume he’s still single? She’s probably some six-foot, blonde supermodel who doesn’t own her own toilet brush.

Charles appears in his office doorway, off the phone. He smiles when our eyes meet. My mouth hangs open. I’m mute. This is a terrible mistake. I panic, twirling an about-face and running for the elevator at full speed.

“Cindy? Cindy! What’s wrong? Wait!” Charles calls after me.

I trip on my sprint into the elevator. The box of Nikes hits the ground behind me. As does the envelope with my letter. But it’s too late. The elevator doors are closing. Charles studies me, then the box of shoes. 

And I’m gone.

Fifteen minutes later I’m driving slowly, smacking my forehead with my palm, when the phone rings. It’s him.

I swipe right. “Hello?”

“Hi.” Charles’ soothing voice fills my car.

“Hi.” Can I please melt into my seat and disappear forever?

“Check your rear-view mirror.” Charles is behind me. He waves. How did he catch me so fast?

“Oh, hi.” I try to sound cool like I didn’t just embarrass myself into dorkdom 2.0.

“So, I have a pair of shoes here. And I think they’re yours.”

“I’m sorry. I didn’t know…”

“Didn’t know what?”

“Did you read my letter?”

Charles exhales. “Yes.”

“You have uh… Olivia. I’m ridiculous. I’m so sorry.”

“Will you please pull over?”

I sigh and turn right into the library parking lot. It’s deserted. Charles parks behind me and is out of his car before I can open my door. He’s carrying the Nike box.

I lower my window, wishing I could die. 

“I think you dropped these,” he says, grinning.

“Oh. Right. Thanks.”

“Did they fit okay?” 

“Yes… These shoes were from you?”

“Duh.” He winks. It’s starting to drizzle. “Do you mind if I get in?”

“Oh. Sure. Yeah. Of course.”

Charles slides into the passenger side and his scent unravels me—spicy citrus.

“I owe you an apology,” he starts. “I should’ve been talking to you tonight instead of calling my little sister, Olivia, for advice.”

“Advice?”

“Yeah. See, I’ve been trying to get up the nerve to ask my dream girl to dinner.”

“Oh.”

Charles lifts my hand from the console between us. His lips graze my knuckles and my stomach turns to hot jelly. “It’s you, Cindy. You’re my dream girl.”

“I am?” I’m having trouble forming complete sentences right now.

Charles laughs, and then his voice grows quieter. “So. Will you?”

“Will I what?”

“Have dinner with me?”

I sigh, sinking my teeth into my lower lip. This is really happening. Cindy-rella and Charles Prince.

“I’d love to.” 

“And Cindy?” Charles leans over to my side of the car, taking my face in his warm hand.

“Yes?”

“I’m glad the shoes fit.”


Courtney Dailey
Courtney Dailey is an award-winning author of contemporary Christian stories with quirky characters and laughable plotlines. She loves a good clean romance. After placing in three categories in the Foundations contests at BRMCWC in 2023, Courtney was also named a finalist in the 2023 ACFW Genesis awards.

When Courtney isn’t pecking away on her keyboard, you can find her chasing entrepreneurial dreams with her lead-man-inspiring husband, chaperoning a field trip for one of her kiddos, or speaking for ladies’ groups at various churches.

Courtney is represented by Blythe Daniel of the Blythe Daniel Agency.

Connect with her through Facebook, Instagram, YouTube, or her website.