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The first time where Caleb almost confessed his was during their Sundays' film nights. She invited him over, as always, to watch their favourite show.
They were both sitting on the couch, lights off except for the soft glow coming from the television. Caleb had one arm wrapped around her waist, his thumb mindlessly rubbing in circles while she had her head nestled on his shoulder. Caleb slowly shifted in his seat, trying to make her feel more comfortable by resting her head on his firm chest, her hair tickling his chin as he rested it on her head.
Except for his heart beating a bit faster than usual, he was feeling fine; yes, maybe not completely focused on the show, but no strange feelings or needs to confess his love to her. That is until she unconsciously gripped his shirt in her sleep. That was enough for him to stop breathing for some seconds. He didn’t move, not for a long time, scared that if he did she would wake up and see how much of a mess he was.
His eyes were on the screen, but he couldn’t hear anything but her soft breathing, his mind spiralling with all the things he wanted to confess right there, when she was deep asleep and not able to hear him. Hesitating, he reached down enough to place a featherlight kiss on her head, his lips not moving from there as he closed his eyes, slowly inhaling her scent.
It made his body shiver as electricity rushed through his veins. His grip on her waist tightened just enough for him to realise he was losing control, so he pulled back enough to grab a blanket, shifting her so delicately that she could swear she was on a cloud and covering her.
After looking at her with a hint of a smile on his lips, he turned off the television and went back home, the cold air of the night helping him to calm down his racing heart.
The second time happened because of alcohol. Caleb wasn’t someone who drank too much, he barely touched the glass, and most of all he didn’t really like parties. That time he was there because she asked him, and how the hell was he supposed to tell her no? Especially when he knew guys would try to hit on her.
The party was too loud, too hot, and Caleb was already calculating how long he had to stay before he could leave without looking rude. He was halfway through nursing a warm non-alcoholic drink when he heard her laugh — that particular laugh she only did when she was tipsy: too loud and too bright.
Then she spotted him.
“Caleb!” she called out like she didn’t see him in weeks, even though they texted less than an hour before. She stumbled over, drink sloshing a little in her hand, cheeks flushed and eyes shining. She was a mess. A beautiful mess. A mess that Caleb loved with every fibre of his being.
Before he could say anything, she threw her arms around his neck and pulled him in. Thankfully his reflexes acted before his mind could think, catching her instinctively as his hands found her waist like second nature. Her body was soft and warm against his, smelling like vanilla and vodka and something distinctly her which always made his head spin.
“You’re my favorite person,” she mumbled, her lips grazing the shell of his ear. And his pulse stuttered. Her perfume was dizzying enough for him, but those words only melted his brain.
“Someone’s had fun tonight,” he said anyway, trying for lightness, trying not to read into the way she’s pressing into him like she belonged there. Like she wanted him even half as much as he craved her.
“Mmm,” she hums. “I missed you.” And he laughed under his breath, raising a brow at her. “I’ve been here the whole time.”
She pulled back just enough to look at him — barely inches between them. Only then Caleb realised how close they actually were and he had to physically contain a groan. Her pupils were blown wide, her gaze unfocused but soft. For a second, he let himself wonder. If she leaned in just a little more. If he closed that tiny gap. The words were ready in his throat, but that single second where he wondered if it could work was enough for her to change subject.
She giggled and said, “You’d be so good for Tara.” probably not even realising how stupid she sounded. He didn’t even speak to Tara that much.
His smile faltered, just a single second. She would have been able to notice it, if only she was sober. “Yeah?” She nodded, then rested her head on his shoulder like she had done it a thousand times. “You’re nice. You’d take care of her.”
He wrapped his arms around her more securely, holding her like she wasn’t unknowingly shattering him. “Thanks,” he said quietly. This girl really was an idiot. An oblivious idiot. And he loved every inch of her, even if it was infuriating sometimes.
Later, when she started to drift and her words slur together, he took her back home. He grabbed her a glass of water and some painkillers, knowing that the next day she would be tired and hurting. He made sure she ate something before tucking her up, ready for bed.
And when she texted him the next morning — “Thanks for looking out for me, Caleb. You’re the best” — he just replies:
— “Anytime, Pipsqueak.” —
The third time was on the rooftop bar: loud, strung with fairy lights and buzzing with Friday night energy. Caleb was nursing his drink, half-listening to the conversation around him, when she sat beside him, effortlessly close. “Hey,” she said, nudging his shoulder with hers. “Come meet Jenna from work!”
He followed her across the rooftop, weaving through bodies and laughter, and landed in front of a tall girl with cool eyeliner and sharper face features. “This is Caleb,” she said, turning to introduce him, already grinning. “My best friend.”
Just like that.
Not “my favorite person” or “my partner in crime.” Just best friend — simple, easy, devastating. He smiled, though. Of course. He always did. And of course he knew that was exactly what they were, but it didn’t mean it didn’t hurt.
Jenna smirked, as if she sensed something in Caleb’s behaviour. “Best friend, huh?” There was a hint of suggestion in her voice, the kind people always thought was harmless. Which it wasn’t, since Caleb’s heart stopped every single time.
“Oh my god,” she laughed, waving it off. “We’ve literally known each other forever. He’s like—family.” Something in Caleb’s chest tightens. Just enough to notice. But he quickly rolled his eyes playfully, if only his jaw didn’t tighten.
Jenna looked him over again, eyebrows raised. “You single?” And Caleb was caught off guard for a second, then recovered. “Yeah.”
“You should meet my roommate,” she said, probably innocently. “She could be kind of your type. Quiet, but cute and soft.” He catch her glance out of the corner of his eye — the one who called him family five seconds ago — but she was just sipping her drink while looking away, uninterested. He internally sighed before turning half his attention back to Janna.
Later, when they were walking back to the car alone, she looped her arm through his like she always did. Warm, casual, possessive in a way that doesn’t mean anything, of course.
She leaned in close, just enough for her hair to tickle his jaw, and whispered, “Jenna’s roommate’s not actually your type. Don’t let her set you up.” That made Caleb’s heart falter.
“Yeah?” he asked, not looking at her. His eyes were fixed in front of them, or otherwise he would have jumped on her right there and then. “No,” she said casually and smiled. “You don’t like soft, perfect girls.”
She didn’t know that it was her he had always been measuring everyone against. Didn’t know that, to him, perfection looked a lot like the way her voice dipped when she was sleepy. Or how she still waited for him to unlock the passenger door before getting in, like some kind of habit he never asked her to form.
He didn’t say any of that, of course. He just smiled like it didn’t matter. But his eyes spoke volumes, and he hoped that she wasn’t looking at him too closely.
After that, she leaned her head on his shoulder like nothing was wrong. And Caleb thought he was foolish for thinking that might mean anything.
The fourth time started like most nights did — casually. She texted him something dumb around midnight:
Pipsqueak <3
Why do all the guys I like turn out to be emotionally stunted or mildly cursed
Pipsqueak <3
Not you though. You’re the blueprint.
He grinned at his screen in the dark, lit only by the glow of the conversation. Of course he was; she just didn’t like him back. And he was fine with that.
You
Lucky me.
Pipsqueak <3
Unlucky me.
You’re the only one I can actually talk to and you’re not allowed to be THIS hot. It’s rude.
He typed out three different responses and deleted them all. How the hell was he supposed to answer to that. Finally, he simply decided to change subject.
You
Go to sleep.
Pipsqueak <3
Make me.
He knew she was laying in bed right now, messy bun slipping out, one leg under the blanket and one out, probably squinting at her phone with that half-drunk-on-sleep smile. The thought made his body shiver and a sigh escape his lips, closing his eyes as his mind was filled with scenarios where he finally shut her up like he really wanted to. But he had to regain control over himself quickly.
You
Seriously, you’re gonna pass out mid-sentence.
Pipsqueak <3
No I’m not. I’m not even tiredddddsdds
That was the last one for a while. He watched the typing bubble appear and disappear a few times, like something was on her keyboard. Probably she was trying to stay awake for him, but she didn’t succeed.
He hovered over the keyboard for way too long before typing something.
You
Sometimes I think I’m in love with you.
You
And sometimes I know.
He stares at those for a long, long time. Then deleted them. It was stupid and reckless and only the gods knew what could happen if she woke up and read them. Instead, he sent another one.
You
Night, trouble. Talk tomorrow.
The message marked as delivered, but not read. He sighed deeply as he placed his phone on the bedside table, groaning and biting down on his bottom lip hard enough to draw blood. He was going insane. He felt like he might explode anytime soon.
She texted back the next morning, bright and chipper. As if he didn’t literally confess his feelings.
Pipsqueak <3
Sorry if I passed out lol. You still there for brunch?
And of course he was.
The fifth time was probably his last straw. It started innocently, as it always did with her in his life.
She was getting ready for something — dinner with friends, maybe even a date (Caleb didn’t ask, not sure if he wanted to know the answer) — and her vanity was cluttered with open lipsticks and makeup brushes. He was sitting on the edge of her bed, scrolling aimlessly and pretending he was not watching her more than his screen.
She turned around suddenly, holding two lipstick tubes like a challenge. Caleb knew that look only meant troubles for his soft heart. “I need your face,” she says.
He lifted a brow, the phone already forgotten on the bed. “That’s… not terrifying at all.” She just grinned. “Don’t be dramatic! Your skin tone is close to mine, and I need to see which one looks better in natural light.”
Before he could even think of arguing, she straddled his legs and settled on his lap like it was the most normal thing in the world and not the hottest thing on earth. Caleb’s breath stopped, heart not beating anymore in his chest and, before he could realise it, then her hand was under his chin, tilting his face to the light. “Stay still.”
She swiped on the first lipstick on her lips — a deep red that made her look dangerous and impossible — and leaned in without hesitation. Her lips pressed softly to his right cheek, a perfect print blooming against his skin. She pulled back slightly, examining her work like a painter checking brushstrokes with a thoughtful look.
“Too harsh,” she murmurs.
And Caleb? He was still frozen, trying to will his heart rate into something survivable. He was fighting the urge to grab her waist, pull her down and let her know how fucked up he was and how fucked up he was going to make her and–
She leaned in again and kissed the other cheek, this time slower, more thoughtful, more like she knew what the hell was happening inside Caleb’s head. He didn’t dare moving, too afraid that his body would betray him.
“This one’s better,” she said, eyes flicking to his with an innocent smile on her lips, and he was on the verge of biting that bottom lip so hard to draw blood. There was a pause. Not long. Just enough for him to come back to his senses. But of course she had to add gasoline to the already burning fire.
Her thumb lingered near his jaw, smudging the edge of the kiss. She was close enough for him to count the gold flecks in her eyes and the freckles on her cheeks. “You’re a really good swatch,” she added, voice too light for how loud everything felt suddenly.
He meant to make a joke, deflect like usual — but his mouth was dry, and she was already standing again, wiping the lipstick off his skin like it never meant anything. He gulped, inhaling deeply through his nostrils as he bit his inner cheek.
He watched her walk back to the mirror, not even caring to look back and him and see the mess she just made with such a simple action. He was on the verge of whimpering, if he had to be honest with himself. His lap now felt cold and empty.
But instead of doing anything, he didn’t say a single word, scared that if he opened his mouth something would betray him.
The only time where he didn’t hide his feeling was a late night. The kind of late that made everything feel softer. Like the world had finally gone quiet enough for honesty to slip in.
They were sitting on her living room floor, backs against the couch, legs stretched out in opposite directions. There were two mostly-finished drinks on the coffee table — hers was emptied and refilled only once, strangely enough — and a playlist humming low through the speakers; one of hers, all slow indie and warm, aching chords.
She had her head tilted back, eyes half-closed, a throw blanket draped over her shoulders like a cape. Her cheeks were flushed from the wine, but not enough to make her sloppy. Just enough to loosen the edges.
“Can I ask you something?” she said, voice low and close, as if she wasn’t so sure about it. He glanced over, catching her gaze. “You just did.” He mocked her with a chuckle. She kicked at him gently under the blanket. “I’m being serious.” His smile softened. “Okay. Ask.”
She paused. Not for drama, but because she was picking her words carefully, which was rare for her. She was nervous this time, Caleb could feel it.
“Have you ever been in love?”
The question hanged there for a second. Not sharp. Not accusatory. Just… open. She was genuinely asking; and his breath caught, but only slightly. He didn’t look away. She was watching him — really watching. Like maybe she already knew the answer and was waiting to see if he would lie.
He considered it. The lie would have been easy. Safer. Something deflective, like “maybe once” or “nothing serious.”
But he was tired. Of hiding, of being considered just family, of swallowing things just because she never asked. “Yeah,” he said. Quiet. Certain. It was happening this time, and Caleb didn’t have the strength to lie a single time more.
She shifted, tucking one leg underneath her, giving him her full attention now. “Yeah?” He nodded just once, eyes still on her beautiful face. “Yeah.”
“Who?” she asked. The word was barely above a whisper, and it landed heavier than it should have. Was she even aware of the effects she had on him? His fingers tightened slightly around his glass. Other than that, though, he didn’t move. It was now or never.
“You,” he said. It wasn’t dramatic. Not whispered like a secret. It was just true.
She blinked — slowly, like she wasn’t expecting that. Or maybe she was. Maybe she hoped and didn’t dare believe it. “How long?” she asked, voice even smaller now.
He laughed under his breath, shaking his head once. Not bitter. Just tired. Honest “You wouldn’t like to know, pipsqueak.”
There was a beat. A long one. The kind that stretched and breathed on its own. She didn’t look away. Her mouth opened, then closed again. She was stunned, not because she didn’t think he could feel this way — but because he finally said it.
“You should’ve told me,” she said softly, and he just shrugged. “You were always dating someone. Or not looking. Or calling me your best friend like that was the end of the conversation.”
“And now?” He looked at her, studying her face, searching for any signs of discomfort or rejection. Her knees were brushing against his. Her lip was caught between her teeth — making him crave it even more, and her eyes were so wide it hurts.
“Now I’m telling you.”
She leaned in slightly, like her body was moving before her mind catches up. The space between them becomes charged, unbearable, and Caleb wasn’t sure it was a good idea anymore. His heart just wanted to explode.
“I don’t want to ruin this,” she whispered, and Caleb couldn’t help but lean even more forward, his lips brushing hers. “Neither do I,” he said, and he said it like he meant it. Because he did. He was so scared that he would run away and never be seen again, if only he could.
Her hand found his knee under the blanket. Fingers brushing slow, unsure. It felt like permission, or maybe a question. Her hand tightened slightly on his knee.
His forehead rested against hers, both of them still, breathing each other in like they didn’t want to break the moment. And gods did Caleb want that moment to never end.
“This feels like a dream,” she whispered and he almost smiled. Almost. “Then don’t wake up.” It was cheesy. Stupid, even, but she laughed — soft and real — and it was the kind of laugh that cracked something open between them. The sound that made him crazy over her.
She pulled back just enough to look at him. Her eyes dropped to his mouth, and his heart tripped over itself at the sight.
But before he could even think of anything, she did more than he would have ever thought, and kissed him. Not hurried. Not dramatic. Just soft — a quiet press of her lips to his, like she was testing something she already knew would change everything.
Caleb didn’t move at first, stunned by the fact that it was really happening. That she was the one doing it. She took the first step, not him.
But then his hands found her waist, pulling her in gently, and he kissed her back — deepening it without really meaning to, but years of holding back were unraveling in a second and he couldn’t stop himself. Her fingers slid up in his hair. She made a soft sound in the back of her throat, barely audible, but of course Caleb noticed it, snd it sent a spark down his spine straight to his core.
It was not desperate, nor rushed. It was full of everything they never said out loud.
When they parted — barely, just enough to breathe, but their lips still touched — she kept her eyes closed for a moment longer. “You could’ve told me sooner,” she said again, this time like it was a regret.
Caleb brushed his thumb along her jaw. “I wanted to. A hundred times. I was starting to go insane.” He whispered, lips brushing against hers.
“Then say it now,” she said, opening her eyes, voice barely there. “Say it like you mean it.” This time he didn’t hesitate, didn’t waste a single second.
“I’m in love with you.”
And this time, she believed him, immediately jumping on him as they kissed once more, ready to explore their feelings together after years of insecurities and tension.