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Published:
2026-02-16
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Valentine's Day - Past & Present

Summary:

Tobias is happily planning for his "first" Valentine's Day with Casey, when someone from his past appears and casts doubt in his mind.

Notes:

I'm a day late - but surprised I was able to finish at all. Life's been busy. I miss Tobias and Casey so much. I still write for them all the time, but not to the "post it" level. But on Valentine's Day, I wanted to make sure I did.

I'm participating in @choicesholidays Valentine's event - this prompt is reconnection, but in a unique way. If anyone is still here to read this - hope you enjoy it! :)

I'm not sure if anyone is around to remember the artwork in the header, but it's from the "Delaying the Inevitable" Days and it was created by the incredible @/artbyainna (IG). I didn't have time for any commissions this year, so I'm borrowing it from myself! :)

Work Text:

 

Tobias had never spent this long choosing a card in his life.

In fact, it wasn’t all that long ago when he wouldn’t have stepped foot into the little gift shop he found himself in, much less spend an inordinate amount of time inside it trying to find the perfect card.

He’d already been through rows of pink and red cards, but none of them were right. Some tried too hard – coming off like a Hallmark movie. Others were too glittery or downright corny. None of them felt like Casey.

Casey. He smiled softly just thinking of her. She wasn’t a woman defined by roses and clichés. No, to him, she was the warmth that brought him through the cold Boston winter. The laugh that could make him smile on his darkest days. She was the light who changed his life, and he loved her. God, he loved her. This Hallmark holiday paled compared to what they shared.

Still, she deserved to feel special on Cupid’s holiday, and Tobias was going all out. He had already ordered the roses – two dozen to be delivered to her at the hospital where they both worked, and another two to their home – well, his home, but she really spent all her time there. He already secured chocolate-covered strawberries in a heart-shaped box – her absolute favorite. And, for good measure, he bought her favorite perfume.

There were still three days until the holiday, but he had it choreographed better than a Tony award-winning play. They’d start with a couple’s spa day at a spot they both loved. That would be followed by a candlelit dinner at Yvonne’s, and afterward, let’s just say what he had planned for her back home made even him blush as he meandered through the rows of red teddy bears and overpriced sweets.

His fingers finally closed around a simple card - ivory paper with a delicate gold script. Its inscription was simple: With you, everything feels like home.

He smiled to himself. “Yeah, this is it,” he said – when a voice pulled him from his thoughts.

“Tobias?”

He turned and came face to face with someone from another lifetime. It had been years since he had seen Rachel Graham, but now she stood just a few feet away. She wasn’t hard to recognize – she looked mostly the same, polished and composed - her delicate features framed by wavy brunette hair that was a few inches shorter than he recalled. And her perfectly arched brows lifted in mild surprise.

“It is you,” she smirked.

“Rachel,” he said carefully. “Hi. It’s been...”

“A very long time,” she replied.

They exchanged the brief, polite pleasantries expected from people who once knew each other in ways that now felt distant. It was an awkward exchange, but not unkind. Then her gaze dropped to the card in his hand, and a soft chuckle escaped her.

“So, who’s this year’s victim?”

The words hit Tobias harder than they should have, his own eyes widening in response.

“Victim?” He said quickly. “There’s no... victim. This is for Casey, my girlfriend, I love her, and...”

He paused because something in her expression caught him off guard. Leaving him feeling cold and defensive in a way he didn’t quite understand.

Rachel folded her arms. “Oh, come on, T. Valentine’s Day? It was always your favorite holiday. Wine, dine, impress… and then some poor woman wakes up in your very expensive sheets, honestly believing you might call again. I’m sure there was a local support group or two back in the day.”  

Tobias’s jaw tightened. “That’s not fair, Rachel.”

“Isn’t it?”

“I was always honest back then,” he said, more firmly. “I never promised anything serious. The women I dated - they knew what I could and could not give. I never gave anyone false illusions.”

She tilted her head, not quite believing. “Maybe. But you also knew when they cared about you a lot more than you did in return – and you were more than happy to let them hope anyway – as long as you got what you wanted.”

The silence fell thick between them. He could hear the words she didn’t say, “including me.” His defences fell. He knew he had never meant to harm her, but he also knew that we don’t get to tell others if we hurt them, so he softened.

“I’m...I’m really sorry if I hurt you,” he said quietly. “That was never my intention.”

Rachel shook her head, raising a hand protectively. “It’s ancient history, now,” she replied, sternly, but not unkind. “Trust me, I’m fine, Tobias. You did no permanent damage here.”

Her eyes flicked back to the card in his hands.

“But, I’ve hoped you’ve changed – for this Casey’s sake. Otherwise – best of luck to her - she’s going to need it.”

And with that, she was gone.

~~~~~

Tobias didn’t want to admit it as he walked home on the cold city streets, but Rachel had gotten to him. No matter how hard he pushed the thoughts away, they kept returning.

Was I that bad? He thought. But the question that haunted him the most was -  and have I honestly changed?

The thought terrified him. His past reputation was colorful, for sure. Even those who loved him most had him painted as an eternal bachelor – his mother and aunties had long given up on expecting more from him. But that wasn’t him anymore, he thought. He loved Casey with all his heart. What they shared was real, deeper than anything he’d ever known in his life. He was confident of that, but Rachel’s voice lingered in his mind, chipping away at that confidence bit by bit - which upset him more than he wanted to admit.

~~~~~

Casey was in the kitchen when he stepped inside. The sleeves of her blue sweatshirt pushed up, long blonde hair pulled into a ponytail atop her head as she stirred something that made his former bachelor pad smell like something he had only recently come to know. Her face lit up the second she saw him.

“Hey, you!” She beamed. “You’re early! I tried a new recipe, and I’m not sure if it’s going to work, it’s...”

She stopped mid-sentence when she saw his face. Because she could read him better than anyone in the world, and one glance told her that all was not right. She placed the spoon on its rest and wiped her hands with a towel, stepping toward him.

“What’s wrong?” she asked softly.

He hesitated, choked on his own words when he started to speak. Then the truth tumbled out without a second thought.

“Are you happy with me? Because I’m… I’m not sure I deserve you.”

Her brow knitted together. “Tobias, don’t be ridiculous,” she replied. “You know how happy I am, and we both deserve each other. Where is this coming from?”

So he told her – about Rachel, about his past, of which Casey was already well aware. But Rachel’s words wouldn’t release him, nor the fear they ignited in his heart – fear that maybe, deep down, he was still the cad people once believed him to be – and Casey deserved so much better than that.  

Casey listened without interruption, and when he finished, she took his hands in hers.

“T,” she said gently, “we’ve all made mistakes. We all look back at things and wish we had made different choices. That’s part of being human. The fact that you’re even reflecting on this says something. People grow, we change – if we do it right – and I think you are.”

She gave him a small, crooked smile. “And if I remember correctly, Boston’s former Casanova did the impossible. He spent months at my side as I walked through the worst time of my life -  celibate as a monk – even though neither of us knew if I’d ever be more than your friend. That doesn’t sound like a shallow, careless man to me.”

She watched him swallow.

“And, besides,” she added softly, “We’re already time-tested. I mean, our relationship is relatively new… but new-new. It may be our first Valentine’s Day...”

He huffed a quiet laugh at their ongoing argument, recalling last year’s freezing Valentine’s trip to an alpaca farm. They were two idiots hopelessly in love, but pretending they weren’t.

“That was our first Valentine’s Day,” he insisted.

“It absolutely was not,” she said, with a smile that melted his heart.

“You were never a bad person, Tobias. Sure - you liked your freedom and weren’t ready to settle down. Maybe you misjudged some situations, but at least you were honest. And... you’re not that man anymore.”

Her eyes were shining brightly as she gazed up at him.“You’re the most loving partner I could have asked for. I think I’m the lucky one in this scenario.”

He felt something inside him break loose. Warmth and love rushed in to fill the crevices where guilt and doubt had started to settle.

“So,” he smiled faintly. “You don’t mind being stuck with me?”

Her smile answered him before a word was spoken.

“I plan on being stuck with you as long as you’ll have me.”

“Then we’ll have to keep loving each other when we’re old and gray,” he murmured, brushing a lock of hair from her face. “Because I never plan on letting you go.”

“Good,” she said, jumping into his arms.  

This kiss that followed was soft and slow – filled with the comfortable familiarity between them, but never devoid of the fire that burned underneath. When they parted, she reached into a small bag on the counter and handed him a tiny chocolate heart.

“Happy Valentine’s Day, baby.”

He let out a little laugh. “But it’s three days away.”

She shrugged, playfulness in her eyes. “When do we play by the rules? We can start celebrating early.”

He stepped toward her, letting out a little groan when his hands found her hips. Dinner sat forgotten on the stove.

“Then I say we start right now...”

And they did – right there and then. And for the remainder of their lives together, Valentine’s Day would always be a multi-day event filled with the playfulness and love that defined who they were. And one thing was for sure: the two of them? They were forever. ❤️