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Perfectly Imperfect

Summary:

Penelope and Anthony’s unexpected connection grows through playful banter, quiet moments, and undeniable chemistry. As they navigate insecurities and small acts of care, they find themselves drawn to each other, igniting the spark of something meaningful.

*Pen/Anthony - If you do not like this ship, just skip*
*Modern AU*

Notes:

A glimpse into how it all started, before Anthony moved to NYC. Hope you enjoy it!

This story is part of the "Back to You" series -
The one Anthony has a dream: A Family for Christmas
The one Anthony goes after the dream: Anthony's Pizza

 

*This is for anyone struggling this holiday season (or any time of the year) with unwanted comments from people close to you. I wrote this for us. Sending much love!*

(See the end of the work for more notes.)

Work Text:

Penelope walked home from the gym, fresh from the spinning class she shared with her friend Edwina twice a week. She enjoyed working out—not obsessively, not in a "this is my entire identity" kind of way. It just felt good to carve out time for herself, to clear her mind, to feel her blood pumping.

She might’ve enjoyed it even more if her mother didn’t feel the need to congratulate her every single time. Compliments from Portia were rare, sure—but did they even count if they made her feel worse instead of better? Because no matter how well-intentioned her mother tried to sound, Penelope couldn't help but hear the unspoken judgment: if she hadn’t worked out, she was somehow less.

But tonight, she refused to dwell on that. No, not tonight. Because in just a couple of hours, the most eligible bachelor in London—scratch that, probably the entire U.K.—was going to pick her up for a date. An actual, bona fide date.

The past few months had been nothing short of... well, interesting. Penelope had somehow found herself spending more and more time with none other than Anthony Bridgerton. Yes, that Anthony Bridgerton. It all began innocently enough—she’d approached him for an interview as part of the “30 in their 30” series she was covering for her internship. A golden opportunity for her career, no doubt.

Of course, it was also absurdly convenient that Anthony happened to be her best friend’s older brother. The man she’d known in passing for years but never quite like this. Funny how life worked sometimes—like it was in on a secret you weren’t yet privy to.

What started as a simple favor quickly turned into something else. She didn’t catch on right away, of course. The man was like a walking marble statue, all polished charm and effortless flirtation. How was she supposed to know that some of that suaveness was actually meant for her and not just his default setting around women?

The last time they went out, it was to celebrate the published article she’d written about him for the magazine. He took her to this ridiculously fancy restaurant in a part of town she almost never ventured to. It had all the trappings of a date—the mood lighting, the candles, the steep price tag. She even dressed like it was a date, just in case. But as much as it felt like one, she was pretty sure he was just being polite, grateful that she had painted him as Anthony—human, layered, interesting—and not just "CEO Anthony Bridgerton."

And then he drove her home. That’s when it happened—the move . A real one. No dancing around it, no guesswork. He looked her right in the eye and said that the next time they went out, he wanted it to be a date. A date date. The kind of bold, self-assured declaration that caught her off guard in the best way possible.

It was sexy. It was refreshing. And honestly, it left her a little breathless. She was a senior in college, and her dating history so far had been… underwhelming, to put it kindly. Most guys her age were a hot mess of indecision, too scared of anything more real than a half-hearted hookup. Anthony, though? He knew exactly what he wanted—and for some inexplicable, thrilling reason, what he wanted was her.

---

She had just stepped out of the shower, the towel clinging to her damp skin as she stood in front of the mirror, water dripping onto the tiles. For a moment, she didn’t know where to start. Her fingers tapped a restless rhythm on the edge of the vanity, a small sound that somehow felt deafening in the quiet room.

If her mother were here, she’d undoubtedly have something to say. Maybe about how Penelope hadn’t been to a nail salon in over six months, her unpolished nails another unchecked box on Portia’s endless list of what is expected of a young lady.

Finally, Penelope looked up, her reflection staring back. Her skin was smooth, always had been, but the old echoes of her mother’s voice crept in. Your cheeks are a little too round, darling. Portia and her sisters all had sharp, sculpted features, like they’d stepped out of a Renaissance painting. Penelope’s face, on the other hand, always felt like an unfinished project—a lump of clay left waiting to be shaped.

She pushed the thought aside with a shake of her head and reached for her hair. The curls were one of the few things she genuinely loved about herself, and she treated them with care. Her curl cream, expensive as it was, felt like an investment in her identity. But Portia didn’t see it that way. Too wild, she’d say, too much frizz.

Penelope sighed and set the curl cream down. Styling could wait. She needed to figure out the outfit first.

She swung open the wardrobe doors and stared at the rows of clothes. Anthony had said the date was a surprise, which left her with almost no clues about how to dress. Her fingers slid through the hangers, pushing aside fabric after fabric. The pink blouse? Too short—Portia had reminded her of that just last week. The blue one? It made her look older, like she was trying too hard to be sophisticated.

Her hands kept moving, her mind cataloging every critique that had ever stuck to these clothes like static. Nothing seemed to fit—not her body, not the occasion, and definitely not the version of herself she wanted Anthony to see.

As doubt began to creep in, slowly overtaking the excitement that had been buzzing in her chest, Penelope reached for her phone. Maybe she should just text him and cancel the date. It wouldn’t be a big deal, right? She was tired anyway—really tired. Her mother was always quick to point out how unbearable she got when she was overtired, how her mood soured and how even her blinking seemed... off. Yes, her blinking. Because apparently, even that betrayed her.

He wouldn’t mind, would he? It wasn’t like Anthony Bridgerton was actually interested in her. Regular guys weren’t interested in her, so why would he be? Sure, he’d been perfectly clear about his intentions, but maybe that was just... politeness. Maybe he felt obliged after the glowing article she’d written about him. It had been a really good article, after all. Too good, maybe. Good enough to make him feel like he owed her a night out. Another one. Or something.

She stared at her phone, the screen casting a soft glow in the dim room, her thumb hovering uncertainly over the keyboard.

Pen: Hey Anthony, I feel I'm coming down with something. Rain check?

Anthony: Ouch, I don’t think I’ve ever been turned down by fake illness.

Penelope snorted. He couldn’t know right? He was just being his obnoxious self.

Pen: I wish I could take credit for giving you a humble check, but I really feel sick.

Anthony: I'm sorry, Pen. Can I get you anything?

Pen: It's all good. Thank you.

---

She felt a little guilty for canceling last minute, but not that guilty. After all, she was fully prepared to make it up to him. She wanted to go out with Anthony—just not today. Not when she felt like this.

Most days were better now. Moving out of her family home had done wonders for her self-esteem, and so had finally choosing clothes that fit her style instead of being stuck with her sisters’ ill-fitting hand-me-downs. She was thriving—acing her studies, setting the groundwork for a promising career, even playing the piano again. It was something she hadn’t been able to do at home, where every note was deemed an inconvenience.

Yes, most days she felt good about herself. Confident, even. Just… not today.

Today, the ghosts of old comments crept in, uninvited and unrelenting. They whispered insecurities she thought she’d outgrown, waved them around like neon signs she couldn’t ignore. It wasn’t every day she felt this way, but when it hit, it hit hard.

And because today was one of those days , she hoped Anthony would let it go. Forgive, forget, and not press the issue. She even started wondering how long it might take for him to text or call again.

Apparently, not long.

She had barely finished pulling on her pajamas, ready for a quiet solo night in, when there was a knock at the door. Anthony was there.

“Anthony? What are you doing here?” Penelope asked, opening the door just wide enough to peek out. Then, remembering herself, she added a theatrical cough for effect.

“I was worried about you. Canceling plans last minute isn’t really you,” he said, stepping inside like he owned the place. He was soaked to the bone, raindrops trailing off his hair and jacket. In his hands were a couple of reusable totes that looked suspiciously heavy. “How are you feeling?”

She blinked at him, momentarily distracted by the puddle forming beneath his feet. “...so wet,” she muttered, watching him leave a damp trail as he carried the bags into the kitchen.

“Already, huh? See, I knew you needed my help,” he shot back, turning around with a self-satisfied grin that made her want to throw something.

Her laugh came out sharp and sudden. “I said you are so wet!” she corrected, half-exasperated, half-amused.

This man. Absolutely unbelievable.

Penelope had just reached for the mop in the broom closet when Anthony stepped in, effortlessly blocking her path. “I’ll take care of that. You, go lay down,” he said, his voice soft but laced with a quiet authority that sent a shiver down her spine.

Her attempt to mask her reaction was laughably bad, and judging by the glint in his eye, he knew it too.

“You can’t mop while you’re still dripping all over the place,” she said, crossing her arms in an effort to stay composed. “Take off your clothes.”

Anthony raised an eyebrow, the corners of his mouth lifting into that infuriatingly smug grin. “Alright, boss. As you wish.” Without missing a beat, he started unbuttoning his shirt right there in front of her.

Penelope froze, her brain stalling for a full second before she blinked herself back to reality. “I didn’t mean in the kitchen!” she blurted. “Go take a shower. Eloise is as tall as you—I’m sure you can find something in her dresser that’ll fit.”

She shoved him toward the hallway, her hands pressing against his back, hating and loving all at once how perfectly her fingers fit the ridges of his muscles. As he moved out of the kitchen, she cleared her throat, tossing in another fake cough for good measure.

Anthony glanced back over his shoulder, clearly enjoying every second of her flustered state. “Anything else, boss?”

“Shower. Dry clothes. Now,” she ordered, trying to sound firm. But her reddening cheeks probably gave her away.

---

While Anthony was in the shower, Penelope started inspecting the bags he’d brought. He’d been to the apartment enough times to navigate it without help, moving around like he owned the place—which, technically, he did. He’d bought it as an investment property, and she and Eloise had just happened to need a place at the perfect time.

Still, Penelope insisted on paying her share of the rent. It wasn’t much, just enough to give her some sense of pride and independence on an intern’s paycheck, but it mattered to her.

The first bag she opened was a chaotic assortment of medications, as though Anthony had walked into a pharmacy and just swept an armful of supplies into his cart. Pain relievers, cough suppressants, antacids, motion sickness pills, and… birth control pills? She couldn’t even begin to guess his thought process. The man had prepared for every conceivable ailment.

The second bag was more straightforward: a large container of what looked like chicken noodle soup and a neat stack of bread rolls wrapped in a bakery bag.

She couldn’t help but smile as she unpacked everything. Anthony had a way of showing he cared that felt so uniquely him—over the top, practical, and endearing all at once. It was the kind of attention she wasn’t used to but found herself appreciating more than she expected.

Anthony strolled down the hallway wearing one of Eloise’s loudest t-shirts—a black one with the slogan Girls Just Wanna Have FUNdamental Rights emblazoned across the chest. On top of that, he’d managed to squeeze into a pair of drawstring cotton shorts that were, frankly, far too short for his comfort.

The shorts served their purpose, though. They were the only ones in Eloise’s dresser with fabric thick enough to be deemed safe , which was particularly crucial given the fact that he’d had no other option than to go commando.

“Don’t say a word,” Anthony warned as he stepped into the kitchen, his expression daring her to break his command.

Penelope didn’t even try to hold back. Her lips curled into a mischievous grin, her gaze shamelessly trailing down to his exposed knees and back up to the slogan plastered across his chest. “I wasn’t going to,” she said sweetly, her voice betraying just how much she absolutely was going to.

“Right,” he said, folding his arms across his chest. “Laugh it up, Pen. Let’s just remember who brought you soup and half of the pharmacy.”

“Oh, I’m grateful,” she said, her tone dripping with mock sincerity. “It just makes it ten times better that you are making a political statement while doing it. And showing your legs.”

Anthony shook his head, muttering something about revenge as he approached the kitchen. Penelope kept giggling, and for a second, he thought that maybe the ridiculous outfit was worth it.

Penelope turned back to the cabinet just as Anthony walked into the kitchen, the sound of his footsteps sending a small flutter through her chest. She stretched up on her toes again, reaching for two bowls on the top shelf, her fingers barely grazing the edge. It was a losing battle, and she knew it.

Before she could try again, she felt him behind her—his presence unmistakable. He stepped in so close that the heat of his body almost touched hers, the space between them charged. Her breath hitched as his arm reached past her, brushing her shoulder ever so slightly as he grabbed the bowls with an ease that felt maddeningly effortless.

He set them down on the counter, but when she turned to thank him, she found him still close—too close. Anthony placed a hand on the edge of the open cabinet behind her, leaning in with a casual, predatory grace that left her pulse racing. His arm hovered beside her head, the subtle flex of his muscles entirely too distracting as her eyes flitted upward.

“You could have asked for help, you know,” he said, his voice low and teasing, the corners of his mouth curving into that infuriatingly charming smile.

She knew he wasn’t just talking about the bowls.

“And you’re one to talk,” she scoffed, trying to sound annoyed but failing spectacularly when her voice wavered.

“I’m a bad influence,” he murmured, his tone laced with a wicked softness that made her stomach flip.

“Maybe,” she said, managing a smirk. “But you’re still a good person for bringing me soup and half the pharmacy.”

He laughed, leaning in just a fraction closer. “You didn’t exactly say how or what kind of sick you were. Had to be prepared.”

Her heart skipped at the way his eyes lingered on hers, his words playful but his gaze serious, as if he was waiting for her to say something—anything—that would break the fragile tension between them.

"But birth control, Anthony? Seriously?" Penelope asked, grabbing the pink box from the bag in the counter behind her, holding it up like it was evidence in court.

Anthony shrugged, looking thoroughly unbothered. "I didn’t know that’s what they were! The box is pink, and they just looked like they were ‘for women.’ You could be having... womanly problems I don’t know about.”

Penelope doubled over in laughter, her sides shaking as she tried to catch her breath.

“What’s so funny?” he asked, crossing his arms with a mock-offended expression. “Do you not think Yasmin could help you?”

“Oh, I know Yasmin can be extremely helpful—for both of us,” she teased, biting her lip to suppress another giggle.

Anthony groaned, dragging a hand through his hair, registering what Yasmin was for. “Great. Now you think I only asked you out to get laid.”

She tilted her head, feigning innocence. “Oh, you didn’t?” she asked, a hint of disappointment lacing her voice.

“No! I mean…” He hesitated, rubbing the back of his neck. “I won’t lie and say it never crossed my mind, but it wasn’t the only reason.”

“So it was one of the reasons?” she shot back, eyebrows raised.

Silence.

Anthony froze, his eyes narrowing slightly as if trying to calculate whether this was one of those moments where no answer would be the right one.

Penelope leaned closer, her eyes wide and sparkling with playful mischief, her voice dropping into a soft, teasing murmur. “Anthony, do you think I’m hot?”

Her lips curved ever so slightly, and she looked up at him with an expression so sweetly innocent yet wickedly sexy that his brain faltered for a minute.

“Yes,” he blurted out, too quickly to disguise how desperately he meant it. “Too hot, actually. For your own good.” His voice dropped, and his eyes turned predatory, dark with intent.

His free hand found hers, fingers grazing her palm before his thumb began a slow, deliberate caress along her fingers, tracing over nails that hadn’t seen a nail tech in months. There was no hesitation, no judgment—just unspoken affection in the way his touch lingered.

His hand trailed up her arm, reverent and steady, brushing over skin she’d spent years hiding under sleeves, even in the summer heat, because her mother insisted it was “too thick.” But Anthony’s fingers didn’t seem to care for her mother’s opinions. His touch said something different entirely—like her arm was something to admire, never to hide.

His fingers found their way to her hair, damp and frizzy from the day, and he began to twirl loose strands around them. He shaped the curls with careful precision, his movements almost playful, but his gaze was anything but. 

He leaned in closer, his elbow pressing against the upper cabinet now, his other hand rising to cup her cheek. Her soft, round cheek—an imperfection in her own eyes, yet one that Anthony held as though it were made of something sacred.

Penelope let out a sharp, flustered breath, a noise so utterly her that it made Anthony grin, his lips quirking in delight. Her lips trembled, parted slightly, her breaths uneven under the weight of his presence. 

And yet, he didn’t rush. He was taking his time—cataloging every feature, like each one was a treasure he was eager to discover, and that he’d never forgive himself for missing.

Anthony’s thumb brushed over her bottom lip, teasing it apart just slightly, his gaze locked on hers with an intensity that made her breath hitch. He’d been doing so well keeping his composure, but all it took was Penelope tilting her head back and closing her eyes to make him falter. His hand slid from her cheek to the back of her head, tangling in her hair as he pulled her in for a kiss.

When their lips met, it wasn’t tentative—it was a collision of want and need. Penelope’s arms wrapped around him, pulling him closer, and when he felt her body align with his as fiercely as he wanted hers, both his hands moved instinctively. They gripped her hips, lifting her effortlessly onto the counter. Her legs curled around his waist, locking him in place like she never wanted him to leave.

Anthony only broke their kiss long enough to let his lips trail down her neck, leaving little bites and kisses that made her giggle, breathless and flushed.

“You’re not actually sick, are you?” he murmured between kisses, switching to the other side of her neck, his grin brushing against her skin. “Because I’m a bit of a germaphobe.”

Penelope rolled her eyes, laughing despite herself. “Why am I not surprised?”

“I just don’t like getting sick,” he said, his lips dipping to her collarbone. “Cuts back on my productivity.” The cheeky grin in his voice was unmistakable, and he looked far too pleased with himself.

“Shut up,” Penelope said, her laugh melting into something softer as her fingers curled into his hair. She pulled him back up to her, crashing their lips together again, silencing whatever smug remark was about to leave his mouth.



Notes:

*I might add more one-shots like this showing their past relationship.
*Update: Check out Anthony's Pizza to see how Anthony will fight to win her back.

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