Chapter 1: Seven Breakups and One Broken Heart

Natalie’s stepbrother—no blood relation—was throwing another tantrum, demanding she break up with me. She agreed. Again. I was gutted.

The pain hit hard, like I’d just been sucker-punched. I slouched deeper into the battered booth at Sullivan’s Bar, the neon beer sign buzzing over my head. My phone buzzed with group texts I didn’t want to read. Every part of me hurt; I couldn’t even tell if it was anger or just exhaustion in my bones.

This was our seventh breakup.

The scene kept looping in my mind: Natalie hugging me, her arms stiff and apologetic, her voice heartbreakingly sincere but already fading.

"Caleb, this is the last time. Tyler broke his leg. He’ll never dance on the street again like you. He’s miserable, and seeing me with you just crushes him. I’m his sister—I have to be there for him."

She said it like she was talking about a sick puppy, not a grown man. Her words stuck with me, sharp and impossible to shake off. Natalie’s eyes flickered away, and she looked so lost I almost reached out to comfort her, forgetting I was the one losing everything. My throat tightened. I twisted my bracelet, staring at the floor because I couldn’t bear to meet her eyes. My voice wavered when I tried to answer, but nothing came out.

"Just let me help Tyler get through this, okay? Then we’ll figure us out. I promise."

I wanted to believe her. God, I wanted to. Her promises dangled just out of reach, always the same warped carrot on a string.

I searched her face, desperate for something real. Five years together, seven breakups, always for the same reason. Even my own brain felt like it was glitching out:

What’s wrong with the main character? If she doesn’t marry you in a month, she’ll die.

Those words rattled around my head, cold and robotic, like a busted GPS in a car spinning off the road. Was I just a background player in Natalie and Tyler’s soap opera?

So I ended up here, in this dive, a cigarette smoldering between my fingers. The jukebox switched to Garth Brooks, and the bartender clattered a glass down the counter. I stared at my reflection in the amber, wishing I could pour myself out and start over. A friend leaned over, curious:

"So, when are you two getting back together this time?"

I watched the smoke swirl up into the stale air. I’d quit smoking for Natalie, but tonight, none of that counted. The bar buzzed with regulars—guys in Carhartt jackets, old-timers with Budweisers, someone cursing at the pool table.

I glanced across the room. Natalie and Tyler, surrounded by our friends, were celebrating the breakup like it was a birthday. I shook my head:

"This time, we’re not getting back together."

My voice came out flat. My friend snorted, totally unconvinced. I stared at the sweating shot glass on the sticky table, half hoping for a distraction, half wishing I could just vanish.

He followed my gaze. Natalie was pushing Tyler’s wheelchair, smiling like it was her job. An hour ago, Tyler was home, acting all helpless, begging us to break up. Now he was glowing, soaking up the attention. The transformation was wild.

Even in the dim bar light, I could see it—his face had gone from tragedy mask to class clown in a blink. Natalie hovered over him, fussing like a mom. The group loved it, buying Tyler sodas, laughing at his jokes like he was some sort of hero.

Today should have been our fifth anniversary. I’d planned to propose. I’ve loved her since we were kids. When the system found me and said, "Natalie is terminally ill. If you want to save her, you must marry her," I didn’t even hesitate.

I’d bought a ring—spent my whole paycheck. It’s still in my Camry’s glovebox, under gas receipts and an empty Tic Tac box. Five years. All those secrets, inside jokes, lazy Sundays. It felt like my heart was being unspooled.

But we’re always breaking up—six times already. Never making it to marriage. Today made seven.

I wondered if there was a world record for this—most breakups before an engagement. The idea made me want to laugh and scream all at once.

Sitting in that corner, half drunk, I caught Tyler looking at me. He raised his chin, smug, and leaned in close to Natalie on purpose:

"Sis, did you really break up with him? He’s just letting you go?"

He dragged out "Sis" so everyone could hear, his voice syrupy, almost taunting. I could feel the challenge in his stare.

"He knows I can’t leave you, so he tries to keep you to himself. He knows my health is bad, but he just wants to push me over the edge."

Natalie just smiled, not denying a thing. She didn’t bother to smooth things over anymore. She softened her voice for Tyler, comforting him.

She patted his shoulder, all motherly. I felt like a ghost, invisible, fading into the background.

"Should I make it official? Tell our parents I broke up with Caleb?"

She tapped at her phone, thumb flying over Facebook, changing her status to single and letting the whole world see. The message was out: Caleb’s out, Tyler’s number one again.

Tyler watched her finish and planted a gleeful kiss on her cheek:

"I knew Sis loved me most."

He shot me a look like I was nothing. My fists clenched under the table.

It took every ounce of willpower not to jump up and say something I’d regret. I gripped my glass tighter, knuckles turning white. The jukebox crooned a sappy country tune. Life’s little joke.

Honestly, this breakup was a farce. Tyler found out Natalie was going on a trip with me for our anniversary and lost it—right in front of me. But with her, he put on the waterworks, red eyes, actual tears. He even left his wheelchair and crawled across the floor, sobbing:

"Sis, don’t go, I need you… If I weren’t your stepbrother, could we be together?"

It was like a bad high school play, except we were way too old for this. People stared, but Natalie didn’t care. Her whole world shrank to Tyler, right there on the carpet.

Natalie, who’d been brushing it off, suddenly looked shattered. She turned to me and said:

"Let’s break up, Caleb. Tyler’s health is fragile. He can’t take any stress. You’re healthy—just give in to Tyler."

She couldn’t meet my eyes. Her voice was small but final. My jaw locked so hard it hurt.

Right then, I was just… tired. Even if I spent a lifetime with Natalie, I’d never matter as much as her stepbrother.

It was like swimming against the tide. No matter how hard I tried, I always ended up back on the shore—without her.

I knocked back my drink. My friend teased:

"Given your track record, you two will get back together again."

His voice was light, but it felt like salt in a wound. I managed a brittle laugh, praying he couldn’t see how close I was to breaking.

I forced a bitter smile. The cigarette burned my finger, but I let it.

That pain was something real. I let the ash drop, crushing it out with my palm. The scent of burned skin mixed with stale beer and peanuts.

Five years. So many breakups and makeups, and every time, I caved first. I was terrified her illness would steal her away. I wanted to save her. So I did everything I could to hold on.

Love made me a fool, over and over. My friends joked about it, but I wore their laughter like armor, hoping it’d make me less vulnerable. It never did.

After every makeup, Natalie would come to me just like now—gently holding my burned hand, lowering her eyes the way obedient kids do when they’ve learned not to talk back, blowing on my skin.

"How’d you burn yourself, Caleb? I just saw you and couldn’t believe it. You show up and don’t even tell me?"

Her voice would turn soft, her thumb tracing circles on my hand. She always made it feel like I was the one who needed her, not the other way around.

I just stared at her, letting her fuss. My friend noticed, shook his head, and slipped away, like he already knew how this story ended.

He patted my back, mumbling something about tacos before last call. The air in the bar pressed in around me.

"Why aren’t you talking, Caleb? Let’s go home, okay? Tyler’s calmed down now. Let’s go back and talk."

I wanted to ask: Do I even have a home anymore? But I just nodded, numb and following the script.

As soon as she finished, sure I’d be fine, she turned and pushed Tyler out of the bar. I followed, out of habit, watching as she and the driver helped Tyler into the car. She slid in next to him. Only when the door was about to close did she remember I was still there. She hesitated, then told me to get in too.

But Tyler tugged her sleeve:

"Caleb, you and Natalie aren’t a couple anymore. That seat’s mine now."

He gave her that wide-eyed look, all innocent and hurt. If I didn’t know better, I might’ve bought it too.

"And didn’t you two already break up? If people see you together, it’ll look bad for Natalie’s reputation. So, Caleb, don’t ride in the same car as Natalie anymore."

I looked at Natalie, begging for a sign. She seemed relieved, nodded, her hesitation melting away:

"Tyler’s right, Caleb. You take another car home."

Her tone was gentle, but it slammed shut like a door in my face.

My nails dug into my palm. My stomach twisted. By the time I looked up, their car was already gone, exhaust hanging in the air. She knew I hated riding in strangers’ cars. Typical.

I watched the taillights fade, streetlights flickering overhead. I stood there, shivering, the night biting through my jacket. It felt like the universe was telling me to get lost.

My phone buzzed. A message from Natalie:

"Pat pat, Caleb, Tyler’s just being willful. I’ll scold him when we get home. Don’t mind him."

Her texts always came with those silly stickers—this time a kitten, tail curled, fake-pouting. I could almost hear her voice, teasing but always just out of reach.

"When he feels better, let’s get back together, okay? Let’s get married."

It sounded so easy in a text. I stared at the message until the screen went dark.

She even attached a cute sticker of a kitten acting spoiled.

The cartoon face reminded me of all the times she’d pouted in real life, coaxing me into forgiving her. I almost smiled. Almost.

I didn’t reply. She’d said the same thing six times before. Every breakup, she’d coax me like this. That’s how she always got me back. But it was always the same cycle.

My thumb hovered over the keyboard, but what was left to say? I tossed the phone onto the passenger seat, the silence in my car pressing in.

The first breakup? Tyler saw a dance video and bawled until she stayed with him. The second, he got hit by a car on the way to a concert—remembered his old injury, had nightmares, begged her to break up and stay with him. The third, Tyler got a fever—same thing. He wanted her there.

I remembered every excuse, every tearful scene, every time I sat on the sidelines while Natalie rushed to him. My love became a waiting room, and Tyler always got called in first.

Every time, Natalie would look at him with those worried eyes and give him whatever he wanted. Every time, she could let go of me.

Sometimes, I thought I could change things—if I was just more patient, more understanding. But Natalie’s world always tilted toward Tyler, and I was left chasing her shadow.

The system screamed in my head:

Don’t worry, the main character’s just confused. You two will have a happy family, and a super sweet daughter—your favorite little princess. Don’t give up, Caleb! You’ve loved Natalie for so many years. You’ve broken up so many times—one more won’t matter. Just try a little harder this last month. Get her to marry you.

Even my own mind sounded desperate, clutching at fairy tales. Happy endings were for other people. I was starting to see that.

All these years, I stubbornly tried to save Natalie. Even if she left me for a thousand reasons, I never lost hope. But this is a one-man show—I can’t do it alone.

I gripped the steering wheel until my knuckles went white, the hum of the engine my only company. The world outside felt colder, emptier. It was just me and my regrets, driving through the dark.

I dragged myself home. The porch light flickered above me, bugs dancing in the yellow glow. I shoved my keys in my pocket, pretending I wasn’t hoping for a different welcome. The warm light from the second-floor window showed Natalie’s silhouette, bent over, playing some face-to-face game with Tyler. But she’s always been protective of her face—never let anyone touch it, afraid of breakouts. Before, if I even tried, she’d pull away instantly, her voice cold:

"Don’t touch my face."

That automatic rejection stung. But now, she’d forgotten all about it—pressing her face close to Tyler’s, no sign of discomfort.

I lingered in the driveway, headlights still on, watching the shapes on the curtain. It was like seeing my life through a window I wasn’t allowed to enter.

Maybe my footsteps on the stairs were too loud. I interrupted them. Natalie’s smile faded. Tyler went silent. The feeling of being shut out was suffocating.

It was like I’d walked in on a secret I was never meant to know. My chest squeezed tight, and for a second, I thought about leaving for good.

After a while, Natalie seemed to remember herself and came to greet me:

"Caleb, you’re back? Have you eaten?"

Her voice was polite—almost formal. Like I was a guest, not the guy paying the mortgage.

I shook my head.

My stomach growled, but the idea of food made me sick. I looked at my shoes, the scuffed floorboards I’d refinished last summer—anywhere but her face.

"Mrs. Parker made dinner. Make sure you eat, Caleb. By the way, Tyler wants to stay in your bedroom. Caleb, move out and let Tyler have your room."

Her words knocked the breath out of me. Like she was asking me to change TV channels, not give up my bed. I stared at her, stunned.

I stared at her in disbelief.

"This is my house. Why should I move out?"

"How thick-skinned do you have to be to say something like that?"

Her words came out sharper than I expected. The hallway felt electric, like every old fight replayed at once.

The system and Natalie’s voices crashed over me at once:

"Caleb!"

"Caleb!"

My temples throbbed. I felt stuck between my own desperation and her coldness, with Tyler waiting to take center stage.

Natalie’s face shifted instantly:

"What are you talking about! It’s just moving to another room—not like I’m kicking you out. Can’t you give in to Tyler? His leg is broken. Every time he sees you dance, it makes him feel worse."

She pleaded with her eyes, but there was an edge to her voice. Like she expected me to cave, as always.

I was shaking with anger, the taste of blood in my mouth, staring at Natalie. She thought I was just being stubborn and frowned even deeper.

"Caleb, you can’t compare to Tyler. He’s not healthy, you’re perfectly fine. Just seeing you makes him feel worse."

My jaw clenched. Years of resentment boiled up. I wanted to shout that I was hurting too—but what would be the point?

Tyler nodded along:

"Caleb, is it because you hate me that you won’t switch rooms? Don’t you like my sister? If you can’t even do this, how could you ever be my brother-in-law? Dream on!"

His voice was sing-song, childish and cruel. He leaned forward in his wheelchair, eyes sparkling with satisfaction.

After that, I saw Natalie glance at me—disappointment flashing in her eyes. She shook her head, then stormed into my room. Without mercy, she tossed all my bedding and belongings out like trash—including the ring I’d bought with my first paycheck as a dance instructor, our token of love. The ring rolled twice, fell from the upstairs landing to the first floor, and vanished. My heart clenched. I leaned over the railing, searching, but the ring was gone.

I scrambled down the stairs, hands shaking, sifting through laundry and old mail. Nothing. The ring—our ring—gone, like everything else I’d tried to hold on to.

Natalie pushed Tyler into my room. The door slammed shut. Instantly, I heard their cheerful voices inside.

Their laughter cut through the wall, too loud, too bright. I pressed my forehead to the door, wondering if they’d even notice if I left for good.

Tyler laughed: "Sis, what’s this? Your wedding photo with him? So ugly—I want to throw it away."

Natalie doted on him: "Sure, toss it if you want."

I heard the crumple of paper, the careless toss into the trash. A piece of my life, discarded like a used napkin.

Half an hour later, Natalie came out with a garbage bag. Seeing my lost expression, she sighed:

Her shoulders slumped for a second, just a flicker, before her mask slipped back into place. She held out the bag, like she was offering a favor.

"Caleb, you’re Tyler’s brother-in-law. Why can’t you be more understanding? It’s just changing rooms."

She shoved the garbage bag into my hands, like ordering a dog:

The plastic crinkled in my hands, heavy with old memories and the faint smell of her vanilla lotion.

I stared at the bag, the weight of it almost comical. I wondered if she could see the heartbreak in my eyes—or if she even cared.

"Go on, help us throw out the trash."

My chest squeezed so tight it hurt. I heard my breath hitch, but I couldn’t let her see me break.

I forced myself to stand tall, looking down at the face I’d loved for so many years:

I spoke quietly, but every word burned. "We’ve already broken up. Natalie, you two should move out. Don’t take over my things."

Surprise flickered in her eyes. She clearly hadn’t expected me to take this seriously. She compromised, stepping forward and burrowing into my arms:

She smelled like her favorite vanilla body spray, the one she always wore when she wanted something. For a second, I almost caved.

"You know, Tyler used to dance street like you. If he hadn’t saved me, his leg wouldn’t have been broken. I can’t abandon him—I have to take care of him. Didn’t we agree? After I comfort Tyler, we’ll get back together. It’s just switching rooms—it’s not a big deal."

Her voice was syrupy, almost pleading, but I could feel the distance between us like a canyon. I closed my eyes, breathing her in, wishing things could be different.

The system piped up in my mind, voice soft and warning:

It sounded like a whisper behind my ear, promising happy endings that never seemed to come. I’d heard it all before.

"That’s right. As long as you work hard, you’ll be together in the end. The main character’s life is at stake—can you really give up? Besides, you’ve been childhood sweethearts. You’ve loved her since you were little. It’s just a small thing—endure it, and it’ll be over."

I stood in the hallway, clutching the trash bag, wondering when I’d finally run out of forgiveness—or if I ever would.

The hallway felt colder than outside. I told myself I could leave, but my feet wouldn’t move. Not yet.