What if's with Caleb

What it's like if you started dating?

Dating Caleb was like stepping into a world where reality blurred with something almost dreamlike.

At first, it didn't feel real. You had spent so much time by his side as a friend that transitioning into something more felt natural and terrifying. The first time he held your hand as something more than just your best friend, your heart nearly leaped out of your chest. You could still remember how his fingers had curled around yours, firm yet hesitant as if he was afraid of breaking whatever fragile thing had just begun between you two.

Caleb was an enigma of contradictions. He was confident and composed in public, a quiet storm that turned heads with nothing more than a glance. But in private, he was something else entirely. He was thoughtful, soft-spoken in moments that mattered, and fiercely protective in a way that made your heart ache.

Dating him meant stepping into that duality.

Mornings with Caleb were slow and peaceful. He wasn't a morning person, often groggy and unwilling to leave the warmth of the bed. If you stayed over, he'd wrap an arm around you and bury his face into your shoulder, mumbling something unintelligible as he refused to let you move. It took effort to get him up, but once he was awake, he'd be the one making coffee, handing you a cup with a sleepy half-smile.

"Drink," he'd say simply, voice still thick with sleep. "You'll need it to deal with me today."

You'd roll your eyes, but the warmth in your chest never faded.

Afternoons were different. Caleb was focused, and intense when he worked, whether it was training, studying, or anything else that demanded his attention. But he always made time for you. Even when he was busy, he'd pull you into his world, whether it was letting you sit beside him while he worked or stealing moments to text you between tasks. He wasn't the type to send constant messages, but when he did, they were always meaningful.

[Are you eating?] [Be careful on your way home.]
[Miss you.]

Simple. Direct. But every word carried weight.

Evenings with Caleb were where he truly came alive. He had a magnetic energy, drawing you in whether it was through playful teasing, deep conversations, or moments of quiet companionship. He loved to test your patience, poking fun at you just to see you react, but there was never any real malice behind it.

"You make it too easy," he'd smirk after successfully flustering you, eyes gleaming with amusement.

But for every teasing remark, there was an equal measure of tenderness. Caleb wasn't one to express his feelings with grand speeches, but he showed them in his actions. The way he'd walk on the side closest to the road when you went out. The way he'd notice when you were tired and wordlessly offered his shoulder for you to lean on. The way he'd pull you closer when he thought you weren't paying attention, pressing his forehead against yours like it was the only way he could express what he felt.

And then there were the nights.

Nights with Caleb were quiet, filled with whispered conversations and the comfort of simply existing beside each other. Some nights, he'd lay beside you, staring at the ceiling, sharing pieces of himself he didn't let anyone else see. His past, his fears, his dreams, all unraveling in the space between your heartbeats.

"Sometimes, I don't know what I'm doing," he'd admit, voice barely above a whisper. "Like I'm supposed to have everything figured out, but I don't."

You'd squeeze his hand, grounding him. "No one has it all figured out. You're not alone in this."

His fingers would tighten around yours, and for a moment, he'd say nothing. Then, he'd exhale, the tension in his shoulders easing just a little.

"Yeah," he'd murmur. "I guess I'm not."

Dating Caleb wasn't a fairytale. There were arguments, moments where his temper flared and your patience wore thin. He could be stubborn, unwilling to talk when something weighed on his mind. But he was also someone who never walked away from a fight unfinished. Even when the arguments were difficult, he'd always come back, always try to mend what had been cracked.

"I don't want to lose you over something stupid," he'd say after the dust had settled, his voice raw with honesty. "You matter too much to me."

But one night, after an especially heated argument, Caleb had stormed off, only for you to find him later, curled up on the couch, looking pale and drained. His body was warm to the touch, his usual sharpness dulled by exhaustion and fever. The stress had taken a toll on him, and you felt a pang of guilt as you knelt beside him, pressing a cool cloth to his forehead.

"You're burning up," you murmured, brushing his damp hair back.

He blinked up at you, his stubbornness flickering for a moment before giving way to vulnerability. "I didn't want to bother you."

You sighed, shaking your head. "You don't have to handle everything alone, Caleb."

For once, he didn't argue. Instead, he let you take care of him, leaning into your touch as you ran your fingers through his hair, offering quiet reassurance. It was a rare moment, one that reminded you just how human he was beneath all that strength.

And that was the thing about Caleb. When he loved, he loved with everything he had. He wasn't someone who did things halfway. If you were his, you were his completely.

So even on the hard days, even when things weren't perfect, you never once doubted that you were loved.

Because with Caleb, love wasn't just words.

It was in the way he looked at you like you were his entire world.

It was in the way he held you like he was afraid to let go.

It was every little moment that made up the life you were building together.

And you wouldn't trade it for anything.