Updated Feb 24, 2026 • ~8 min read
POV: Cal
Cal had a plan. Perfect proposal. He’d been planning for weeks. Nash was helping. This was going to be amazing.
The plan: sunset dinner cruise. Private boat. Vancouver harbor. String lights. Champagne. Violinist. Propose as the sun sets. Romantic. Instagram-worthy. Perfect. Blair would love it.
Except the day of the proposal, everything went wrong.
Morning started badly. Cal woke up sick. Food poisoning from last night’s questionable sushi. He was in the bathroom, miserable.
“Are you okay?” Blair asked through the door.
“Fine! Just… stomach thing.”
“Do you need anything?”
“No! I’m good!”
He wasn’t good. He was dying.
By noon, Cal had recovered enough to move. Shaky. Pale. But determined. Blair was at work. Perfect timing. He had six hours to prepare. Nash arrived with supplies.
“You look terrible.”
“I’m fine. Let’s do this.”
“If you puke on the boat, she’s saying no.”
“Not helping.”
Three PM: picking up the ring from the jeweler. Traffic was a nightmare. Accident on the bridge. Cal was stuck, panicking. “Come on come on come on.” Finally moved. Got to the jeweler with minutes to spare.
“Cutting it close, Mr. Montgomery.”
“You have no idea.”
Four PM: setting up the boat. String lights weren’t working. Half the bulbs were dead.
“Did you test these??” Cal asked Nash.
“I thought you tested them!”
“Why would I test them?!”
“Why would I?!”
They scrambled. Found replacement bulbs. Half-working lights better than nothing.
Five PM: Violinist canceled. Text message: Sorry, family emergency. Can’t make it.
Cal was going to scream.
“It’s fine. We’ll use a speaker. Playlist.”
“It’s not the same—”
“It’s fine. She won’t care.”
Cal hoped that was true.
Five-thirty: Cal went home to change. Shower. Suit. Cologne. Looking good. Feeling terrible. Stomach still queasy. “You’ve got this,” he told his reflection. “You’re going to propose. She’ll say yes. Everything’s fine.”
Six PM: picking up Blair from work.
“Where are we going?”
“Surprise.”
“I’m not dressed for fancy—”
“You’re perfect. Trust me.”
She was in work clothes. Slightly rumpled. Not the elegant dress he imagined. But beautiful. Always beautiful.
They arrived at the marina. Blair was confused. “Are we… boating?”
“Dinner cruise. Surprise.”
“Cal, I get seasick—”
His stomach dropped. “What?”
“I get seasick. I thought you knew?”
He didn’t know. How did he not know this?
“We don’t have to go—”
“No, it’s sweet. You planned this. I’ll take Dramamine.”
She didn’t have Dramamine. This was a disaster.
They boarded. The boat was nice. String lights working (mostly). Champagne chilling. Catered dinner waiting. Blair looked impressed.
“Cal, this is beautiful.”
“Yeah?”
“Yeah. What’s the occasion?”
“Just… wanted to do something special.”
“Mission accomplished.”
Okay. Maybe this was salvageable.
The boat departed, cruising Vancouver harbor. Sunset starting. Perfect timing. Cal had rehearsed his speech. Got the ring in his pocket. Ready. Then the boat’s engine sputtered and died. They were dead in the water.
Captain announced: “Folks, we’re having a small mechanical issue. Nothing to worry about. We’ll have it fixed shortly.”
Blair looked at Cal. “Did you know about this?”
“No. This is… unexpected.”
Understatement.
They waited. Fifteen minutes. Thirty. Sunset was happening without them moving. Perfect photo op ruined. Cal was stressed. Blair was oblivious, enjoying the champagne.
“This is nice. Peaceful.”
“Yeah. Peaceful.” Panicked. But peaceful.
Engine started again. Finally. They started moving. Cal was relieved. Okay. New plan. Propose during dinner. Not sunset. But still romantic.
Dinner was served. Looked amazing. Salmon. Asparagus. Fancy presentation. Blair took a bite. Choked.
“Is there shellfish in this?”
“I don’t know. Why?”
“I’m allergic to shellfish.”
SHE’S WHAT.
“Since when?!”
“Since always! Cal, you know this!”
He didn’t know this. How does he not know basic things about his girlfriend?
They called the caterer. Yes. There was shellfish. Cross-contamination. Blair couldn’t eat any of it. She wasn’t in danger. Just couldn’t eat.
“I’m so sorry. I thought I told them—”
“It’s okay. I’m not that hungry anyway.”
She was being kind. This was a nightmare.
Cal’s plan was falling apart. No violinist. Broken engine. Inedible food. Blair was seasick and hungry. This was the opposite of perfect.
He should wait. Reschedule. Try again when things were better. But looking at Blair, smiling despite everything, laughing about the disasters. “This is very on-brand for us. Nothing ever goes smoothly.”
She was right. Their relationship had never been smooth. Why should the proposal be different?
Cal made a decision. Screw the plan. Perfect is overrated. He got down on one knee. Right there. Boat still rocking. Broken lights flickering. No food. No violinist. Blair’s eyes went wide.
“Cal? What are you—”
“Blair Sutton. This proposal is a disaster. Everything went wrong. You’re seasick, hungry, and I forgot you’re allergic to shellfish. The violinist canceled. The engine died. The lights are broken. This is objectively terrible.”
She was laughing and crying.
“But that’s us. We’re disasters. Our entire relationship has been one disaster after another. Getting fired. Getting benched. Breaking up. Twice. Long-distance. Medical crises. Policy battles. None of it was smooth. Or easy. Or perfect.”
He pulled out the ring.
“But it was ours. And I wouldn’t change any of it. Because every disaster led us here. To this moment. Where I’m asking you—on a broken boat, with no food, and terrible mood lighting—to marry me.”
Blair was full-crying now. “You’re insane.”
“About you. So… will you? Marry me? Deal with more disasters? Build a chaotic, imperfect, beautiful life together?”
Blair dropped to her knees. Face to face with him. “Yes. Obviously yes. A thousand times yes.”
He slid the ring on. Perfect fit. She kissed him. Hard. Desperate. Happy. Behind them, the captain started clapping. Boat crew joined in. A random couple on the boat they didn’t know was there: also clapping. It was perfect. In the most imperfect way.
“I’m sorry the proposal was a disaster,” Cal said.
“Are you kidding? It was perfect. So perfectly us.”
“The violinist canceled—”
“I don’t need a violinist. I need you.”
“The dinner was inedible—”
“We’ll get pizza after.”
“Nothing went according to plan—”
“Good. Our best moments never do.”
They sat on the deck. Engaged. Blair was staring at her ring.
“It’s beautiful.”
“You like it?”
“I love it. I love you.”
“I love you too. Future Mrs. Montgomery.”
“Oh god. Am I taking your name?”
“You don’t have to—”
“No, I want to. Blair Montgomery. Has a nice ring.”
“Pun intended?”
“Always.”
The boat returned to harbor. They disembarked. Found a pizza place. Grabbed slices. Ate on the pier. Most un-romantic engagement dinner ever. Perfect.
Blair posted a photo. Her ring. Pizza in background. Caption: He proposed on a broken boat with no food. I said yes because he’s perfect even when everything else isn’t.
Comments exploded immediately. CONGRATULATIONS!! THIS IS SO ON BRAND FOR YOU TWO. Couple goals!! When’s the wedding?!
They called their people. Sienna first. She screamed. “FINALLY! I’ve been waiting for this!”
“It just happened an hour ago—”
“I’ve been waiting since the day you met. Tell me everything.”
Blair did. The disasters. The proposal. The yes. Sienna was dying laughing. “Of course nothing went right. That’s so you two.”
“Everyone keeps saying that.”
“Because it’s true. You’re chaos personified. But happy chaos.”
Cal called Nash. “She said yes.”
“YES! Congrats, man!”
“Everything went wrong. Every single thing.”
“But she still said yes?”
“She said yes.”
“Then it was perfect. Congrats. I’m happy for you.”
They walked home. Hand in hand. Engaged.
“I can’t believe we’re getting married,” Blair said.
“Believe it. You’re stuck with me now.”
“Forever.”
“Forever.”
That night, lying in bed, Blair asked: “When should we get married?”
“I don’t know. When do you want to?”
“Tomorrow?”
Cal laughed. “Your mom would kill us.”
“True. She’ll want to plan everything.”
“Big wedding or small?”
“Small. Intimate. Just people we love.”
“I can do small.”
“Good. Because I’m not doing this for show. Just for us.”
“Us. Always us.”
They planned in the dark. Imagining. Dreaming. Who they’d invite. Where they’d do it. What it’ll look like.
“I want it outside,” Blair said.
“Vancouver or Seattle?”
“Here. Vancouver. This is home now.”
“Agreed.”
“Spring wedding?”
“Or fall. Cooler weather. Better for a suit.”
“Fall. October. Perfect.”
They were engaged. After everything. All the fighting. Breaking up. Distance. They made it. To this. Forever. Official. Ring and all.
Blair touched the ring. Still couldn’t believe it was real.
“I’m going to be your wife.”
“I’m going to be your husband.”
“That’s so weird.”
“Good weird?”
“Best weird.”
Cal kissed her. His fiancée. Future wife. Forever person.
“I love you.”
“I love you too.”
“No more disasters?”
“Oh, there’ll definitely be more disasters. But we’ll survive them.”
“Together.”
“Always together.”
Blair fell asleep smiling. Engaged. To Cal Montgomery. The man who chose her. Repeatedly. Through every disaster. Every obstacle. Every doubt. He chose her. And she chose him. Forever. Imperfect. Chaotic. Perfectly them. And she couldn’t wait to marry him.
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