Updated Nov 23, 2025 • ~9 min read
Monday morning, I arrived at Morrison Creative to find my desk covered in coffee cups.
Not random coffee. Specific coffee.
Seven different orders from seven different shops across Chicago, each with a note card.
Monday: Dark roast, double shot, oat milk, one pump vanilla – The Original
Tuesday: Iced americano, blonde roast – The Backup
Wednesday: Cappuccino, extra foam – The Safe Choice
Thursday: Pour-over, single origin Ethiopian – The Sophisticated Option
Friday: Cold brew, no sugar – The Practical Selection
Saturday: Honey lavender latte – The Indulgent Treat
Sunday: Regular black coffee – The Honest Truth
At the bottom of the display, one final card:
I don’t know which you prefer now. So I got them all. You’ve changed in five years. I want to learn everything again. – J
“Jesus Christ,” Hayley said from behind me. “That’s either creepy or the most romantic thing I’ve ever seen.”
“It’s both,” I muttered.
My phone buzzed.
Did you find them? Please tell me security didn’t throw them away.
How did you get into the building?
I know people. Also I may have told reception I was dropping off client materials. Which is technically true—the coffee is material for winning you back.
This is excessive
This is Monday. Wait until you see what I have planned for the rest of the week.
I should be annoyed. Should tell him to stop with the grand gestures.
Instead, I tried the honey lavender latte. It was perfect.
The Saturday option. In case you were wondering.
Noted. I’ll remember.
Eric called an all-hands meeting at ten. I walked into the conference room to find Jeremy already there, sitting in on the presentation like he belonged.
Which, technically, he did now as a consultant.
“Morning, Roselyn,” he said, eyes warm.
“Jeremy.”
The meeting covered the Henderson campaign rollout. Jeremy contributed insights that made the entire strategy tighter. Everyone hung on his words.
Halfway through, his foot brushed mine under the table.
I looked up sharply. He was focused on the presentation, face neutral.
It happened again. Deliberate.
I shifted away.
His lips quirked.
After the meeting, I cornered him in the hallway. “What was that?”
“What was what?”
“The foot thing.”
“Sorry. Cramped space. Accidental contact.” His expression was perfectly innocent. “Why? Did it bother you?”
“It was unprofessional.”
“You’re right. I should be more careful.” He leaned closer, voice dropping. “Wouldn’t want people to think we’re involved. Even though we’re married. And dating. And I spent all last night thinking about how you looked in that green dress.”
“Jeremy—”
“Lunch?” he asked. “There’s a Thai place around the corner. Your favorite, if I remember correctly.”
“I have work.”
“You have to eat. Bring your laptop. We can multitask.” He checked his watch. “Noon? I’ll meet you in the lobby.”
Then he walked away before I could refuse.
At noon, I told myself I was only going because I was hungry.
The Thai place was busy, noisy, perfect for a working lunch. Jeremy had already ordered—pad thai, no peanuts, extra lime. My exact order.
“How are you doing this?” I asked.
“Doing what?”
“Remembering everything. The coffee, the food, the pottery class. It’s like you have a file on me.”
“I do have a file on you.” At my expression, he laughed. “I’m kidding. Mostly. Rose, I was married to you for three years. I paid attention. I just didn’t show it well enough.”
We ate and worked. He reviewed my Henderson presentation, suggesting tweaks that made it stronger. We fell into an easy rhythm—me designing, him consulting, both of us building something better together.
It felt like it had in the beginning. Before the company consumed him. When we’d been a team.
“I miss this,” he said quietly.
“Miss what?”
“Working with you. You see things I don’t. Make connections I miss.” He turned his laptop to show me something. “Like this client—they need rebranding, but they don’t know it yet. You’d figure it out in five minutes.”
“Are you offering me a job?”
“I’m offering you partnership. Professional or personal, your choice. Preferably both.”
“Jeremy—”
My phone rang. Charlie.
The easy atmosphere shattered.
“Take it,” Jeremy said, face carefully neutral.
I stepped outside.
“Hey,” I said.
“Hey.” Charlie’s voice was strained. “How are you?”
“I’m… okay. You?”
“Been better.” He paused. “Look, I called because I need to know. Are we really done? Or is this just a break while you figure things out with him?”
Guilt twisted my stomach. “Charlie, I don’t know. I’m sorry. I just need time—”
“How much time? Because I can’t put my life on hold indefinitely while you date your husband.”
“I know. And I’m not asking you to.”
“Then what are you asking?”
“I don’t know!” The admission hurt. “I’m confused and I’m sorry and I never meant to hurt you.”
“But you did. You are.” His voice broke. “I love you, Rose. But I can’t compete with whatever you two have. This pull between you—it’s bigger than anything we built.”
“That’s not true—”
“Isn’t it? Be honest. When you’re with him, do you think about me?”
I couldn’t answer. Because the truth was no. When I was with Jeremy, everything else faded.
“That’s what I thought,” Charlie said quietly. “I’m not going to wait, Rose. I deserve someone who chooses me first. Who doesn’t need six months to figure out if I’m enough.”
“Charlie—”
“Be happy. Whatever that looks like. I really mean that.” He hung up.
I stood on the sidewalk, phone in hand, feeling like the worst person alive.
Jeremy appeared beside me. “You okay?”
“No. I just hurt someone who didn’t deserve it.”
“Charlie?”
I nodded. “He’s not waiting. Not that I blame him.”
“Do you want him to wait?”
The question hit hard. “I don’t know. Maybe? No.” I looked up at Jeremy. “This is your fault. Before you showed up, my life was simple. Planned. Safe.”
“And were you happy?”
“I was content.”
“That’s not the same thing.” He stepped closer. “Content is settling. Happy is actually living.”
“Maybe I like settling! Maybe I’m tired of living dangerously and getting hurt!”
“Are you? Because the woman I had lunch with—the one who lit up talking about design work and laughed at my terrible jokes—she didn’t look like someone who wants to settle.”
“You don’t know what I want.”
“Don’t I?” He cupped my face, thumb brushing my cheek. “You want someone who sees you. Really sees you, not some perfect version. Someone who challenges you, pushes you, makes you feel alive. You want passion and partnership and someone who fights for you.”
“That’s not—”
“You want me.” His eyes held mine. “You’re just terrified to admit it because last time you wanted me, I let you down. But Rose, I swear to you—I’m not that man anymore.”
“How do I know that?”
“You don’t. Not yet. That’s why we have six months.” He dropped his hand. “But I’m going to prove it. Every single day.”
We walked back to the office in silence.
That night, Julie came over with wine and interrogation.
“So you’re really doing this. Dating Jeremy while Charlie walks away.”
“Charlie deserves better than someone who can’t choose him without a six-month trial period.”
“And what do you deserve?”
I sipped wine. “I don’t know anymore.”
“Do you love Jeremy?”
“I loved who he was. I don’t know who he is now.”
“Then find out. But Rose?” Julie’s expression turned serious. “Protect yourself this time. Don’t just give him everything and hope he doesn’t break you again.”
“I’m trying.”
“I know. I just don’t want to watch you fall apart again like you did five years ago.”
After Julie left, I found myself looking through old photos. Me and Jeremy from before everything fell apart.
Young. Stupid. Completely in love.
In one photo, we were dancing in our tiny apartment kitchen. He was spinning me, both of us laughing. I could still remember that moment—the song, the way he’d pulled me close after, the way everything felt possible.
My phone buzzed.
Thinking about you
It’s Monday night. Don’t you have work?
I left early. Turns out running a company takes less time when you have something more important to prioritize.
Jeremy—
I know. Taking it slow. But you should know—every night I don’t get to fall asleep next to you is a night I regret how badly I screwed this up the first time.
You can’t just say things like that
Why not? Complete honesty, remember? That’s the deal.
The deal is dating. Not emotional manipulation.
Is it manipulation if it’s true?
I stared at my phone, not knowing how to answer.
Tell me one true thing, Rose. Something you haven’t said out loud.
I shouldn’t. Should maintain boundaries. But the wine and the photos and his relentless pursuit had cracked something open.
I’m scared
Of what?
Of wanting this. Of letting myself believe you’ve changed and being wrong. Of trying and failing again.
Those are all valid fears
So what do I do?
You be scared. But you try anyway. Because the only thing scarier than trying and failing is not trying and always wondering.
I sat with that. With the truth that I was already in this. Already trying. Already hoping despite my better judgment.
Wednesday’s date. Where are we going?
It’s a surprise. Wear comfortable shoes.
I hate surprises
No you don’t. You hate bad surprises. I promise this will be good.
How can you be sure?
Because I know you. And I know what you love. Trust me.
That was the problem, wasn’t it? Trust.
He’d broken it once. Could I really give him the chance to do it again?
Goodnight, Jeremy
Goodnight, Rose. Day three down. 179 to go.
I fell asleep thinking about coffee shops and Thai food and the way he looked at me like I was the only thing that mattered.
And wondering if six months would be enough to know if we could actually make it work.
Or if six months would just be prolonging the inevitable heartbreak.
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