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Pick Me Up (When I'm Feeling Down)

Summary:

At last, it was going to be a relaxing Friday evening for Penelope. Except the moment she settled onto the couch, adjusted her glasses, and pulled a blanket over her legs, her phone rang.

OR

Penelope is the Bridgerton's designated driver and Anthony needs someone to pick him up from the bar.

Notes:

My little late entry for the "May'de You Look" Penthony Parlor challenge.

Hope you have fun with these idiots ❤️

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

Work Text:

At last, it was going to be a relaxing Friday evening for Penelope.

She had left work, survived hot Pilates, returned home, and arrived at the part of the day she had been looking forward to most: stepping out of the shower, slipping into her silky blue robe and fuzzy slippers, and curling up on the couch with reading material that was decidedly not a peer-reviewed article.

Sometimes, she allowed herself a small reprieve from the all-consuming beast that was her PhD. She had only a year left before defending her dissertation—though, admittedly, she felt she had been saying that for the last 18 months or so. Sleepless nights, endless revisions, and the constant balancing act of rewriting old chapters while drafting the final one had become her normal.

But tonight was supposed to be one of those rare evenings—simple, quiet, easy.

Except the moment she settled onto the couch, adjusted her glasses, and pulled a blanket over her legs, her phone rang.

That alone was unusual. Almost too disruptive for the type of evening she was going for. No one called anymore unless they were her mother or spam, which most times they felt like they belonged in the same category.

But instead of Mother Dearest or an unknown number, her screen read Letter A.

It made a strange sort of sense. Anthony Bridgerton absolutely seemed like the kind of man who preferred calling over texting. 

What didn’t make sense was why he was calling her out of the blue.

Penelope arrived at Mondrich’s Bar & Lounge around 9:30 p.m. The valet tried to take her car to park, but she managed to convince him she would only be a few minutes.

The moment she walked in, her eyes searched for Anthony.

It didn’t take long to spot him—a man in a designer suit and a watch that cost more than her car.

She started striding in his direction when an apologetic Will Mondrich stepped in front of her.

“I’m so sorry I called,” he said quickly. Lowering his voice, he added, “But it’s bad.”

He leaned in closer.

“Like the media will have a field day kind of bad, if I had called the wrong person.”

Penelope shook her head in confusion. Certainly Will had to be exaggerating, Anthony wasn’t one to get drunk—least of all in public. He stuck to one glass. A Scotch, if he was feeling adventurous. That’s how predictable his drinking habits were. 

But when she glanced over at him, she began to understand the urgency in Will’s tone.

Anthony was sitting at the bar, absently playing with two toothpicks that had, not too long ago, belonged to a martini. He tapped them against the counter angrily, making them fight each other while mumbling under his breath.

“I guess you may have a point. Why me, though?” Penelope almost huffed like a petulant child, though she still aggressively crossed her arms like one. “It’s not like he doesn’t have enough siblings.”

“I know, I know… I just called the number labeled Designated Driver on his phone. Didn’t know it was you until you picked up.” Will raised both hands in surrender.

She looked at Anthony again. Now one toothpick was violently stabbing the olive off the other.

“Okay…” Penelope sighed. “What about his fiancée? Have you tried her?”

Will clicked his tongue and let out a low whistle. “I highly suspect she may be behind all of…That.” He gestured vaguely toward Anthony. 

Penelope felt uneasy at the thought. She didn’t exactly believe Anthony and Kate were a perfect match, but they were both the kind of stubborn that would stay together just to prove everyone wrong. Seeing him like this, defeated, hurt more than she cared to admit.

“Look, I tried putting him in the back office,” Will continued, still feeling bad about dragging her to this, “but that somehow made it worse. He started singing and pounding on the door. Someone was about to call the cops.”

Penelope closed her eyes and took a deep breath.

She was going to have a very long conversation with Eloise about how, exactly, her phone number was saved in the Bridgerton family’s devices. Colin too for that measure. 

But first, she needed to get Anthony away from the toothpicks—and the public eye.

“Just help me get him in the car.”

Anthony was a large man. All of the Bridgerton men were, but Penelope hadn’t fully realized just how large until he was folded into the passenger seat of her vintage car. With Will’s help, Anthony was eventually settled and buckled in—mercifully free of any sharp objects.

For someone who had been carrying on a lively conversation with himself moments ago, he went eerily quiet as soon as the car door closed. She’d expected more resistance, too. They weren’t exactly close, after all. 

But strangely, he complied.

“Am I taking you home?” Penelope asked as she started the car.

“No, no. I can’t go home.” He answered much faster than she expected for someone who looked moments away from passing out.

“Bridgerton House, then?”

“Hell no. No, no, no.” He shook his head and hands dramatically. “No.”

“Okay, okay.” Penelope exhaled slowly. “I don’t know what other homes you own in town, and I’m not driving you to your country house at this hour, so you need to give me something.”

As she waited for him to decide, she checked her phone again.

Still no reply from Eloise or Colin.

“Your place.”

“My what?

“Take me to your place.” He smiled.

A bright, wide smile.

She didn’t know he had that many teeth. That anyone had that many teeth, honestly.

Penelope scoffed out a laugh. “Oh lordy, you are drunk.”

Lordy?” Anthony perked up, leaning back in his seat. “That’s a new nickname. I. Like. It.”

He pointed between them.

“I can be Lordy, and you can be Pen…ny.” He squinted, concentrating. “Lucky Penny. Luckily Pen. Penne!” His eyes widened. “I love penne pasta. Penne with carbonara sauce. Yum.” He gasped softly. “Can you be penne and I’ll be carbonara?”

Penelope didn’t know whether to laugh, cry, or both. And somehow in that confusion, the thought of being covered in his sauce made her cheeks hotter than it should have.

“Goodness,” he muttered. “I’m starving.”

She checked her phone one last time.

Nothing.

With a sigh, she decided taking Anthony to her flat. At least there, she’d have better control of both him and the situation.

She shifted gears and finally pulled away from the curb.

“You’ve got good vibration going on in this thing.” He let out a low whistle, motioning to the seats. “No wonder you like driving it.”

Penelope chuckled to herself. “You tell me if you feel sick, alright? I just got it detailed.”

“A woman after my own heart.” He pressed a hand dramatically to his chest. “I appreciate that, Penne. I admire it, even.”

He let out a soft hum.

“You seem like someone who cares, who pays attention to the details. Meticulous. Someone who values the little things in life.”

“Or…” Penelope glanced over briefly. “This car has been in my family for three generations, and I’m just trying to keep it alive a little longer until I finish my PhD.”

Family legacy!” Anthony exclaimed, swinging a finger in her direction. “You understand the importance of tradition. Keeping things alive.”

“Well…” she shrugged. “I am thinking of getting a new one once I have a job that doesn’t have the word assistant in the title.”

“Change is good.” He nodded solemnly, as if delivering wisdom from the top of a mountain. “Change is necessary sometimes.”

Apparently, no matter what Penelope said, Anthony agreed with her. She knew he was drunk, but it still felt oddly satisfying.

“If we want to be better, we need to change, right?” He continued. “Change is…”

“Anthony,” she said softly.

But he kept rambling.

“Why are we so resistant to change? Why? Change is what moves the world. It’s how we evolve, and—”

“Carbonara,” she interrupted.

That immediately got his attention, so she carried on.

“You want to talk about what happened tonight?” 

“What is tonight?

“I’ve known you for fifteen years, more or less. I’ve been to more Bridgerton parties, galas, birthdays, and game nights than some of your siblings have. I’ve never seen you like this.”

“Hm.” He loosened his tie and ran a hand through his hair. “You mean handsome like this?”

She bit back a chuckle. Of course was distinctively attractive—the kind of man who belonged on the cover of magazines. Realistically, he could have had an entire career posing in nothing but swim trunks or expensive underwear, but instead he spent his days in three-piece suits and boardrooms. 

But she refused to give him the satisfaction of knowing she agreed he was handsome—especially when he was being this inconvenient.

“I mean drunk like this,” she said, clearing her throat.

“I will have you know…” He swirled a finger in the air. “I’m the sexiest man alive.”

He paused dramatically. “In capital letters. Sexiest. Man. Alive.

“I'll have to add some ‘Anthony Bridgerton affirmations’ to my daily routine,” Penelope joked, while simultaneously considering that it could be true. “Do you usually do it in front of the mirror?”

He snorted. Twice, then he laughed.

“The biggest mirror you can find, Penne mia. The longest too. One where you can see everything.” He gestured with his hands. “Every single thing. I’m thinking of having one in the ceiling too, right above the bed.”

Penelope frowned in confusion for a moment, then it registered.

“Oh, that is not what I—” she tried correcting, but he kept going.

“You would look so pretty,” he murmured, almost dreamy. “I just know. Me standing behind you while I bend you over and…”

The rest came out nearly inaudible. It did not matter, it still had an effect on her she much preferred to ignore.

“Okay, moving on now,” Penelope interrupted quickly, before this somehow got even worse. “What’s going on with you?”

“Nothing,” he replied with a hiccup.

“I don’t believe it. You’re, like… the responsible one.” 

He let out a dry laugh. "I am, aren’t I? Responsible. Reliable. The one they come to when they need bailing out," he started counting with his fingers. "Money. Ergonomic chairs. A yacht. Korean skincare. Flights. Tacos. Pink pony with wings.”

“Well, damn. If I’m your designated driver, consider yourself my direct supplier of skincare and tacos.” Penelope glanced over at him. “Do you fly them in fresh from Korea and Mexico too?”

Penelope tried to tease to lighten up his mood, but he was too far gone in his self-pity to take the bait.

Pony with wings,” he huffed, shaking his head and completely ignoring her question. “It’s called a Pegasus, for goodness’ sake. I paid for the best education for that?

He crossed his arms with justifiable indignation.

“They ask me for everything under the sun, except for a job.

“So…” Penelope glanced over at him. “You’re telling me you got drunk because of your demanding siblings? That doesn’t check out. Your liver would be at risk by now if you drank every time they asked for something ridiculous.”

Anthony went quiet.

He turned toward the window, resting his head against the glass—only to accidentally hit it harder than intended.

He cursed under his breath.

Penelope bit back a laugh. They were almost at her place, so she decided not to push for now.

Anthony grew quieter during the last stretch of the drive, which Penelope was okay with. Still, every now and then, she glanced over to make sure he was still awake. When they arrived, she helped him out of the car, and together they stumbled up the steps of her building.

Eventually, they made it to her floor.

The moment she unlocked the door, Anthony headed straight for the couch and threw himself onto it. Inevitably, he was too big for it. 

Penelope tugged at the sleeve of his jacket, prompting him to stand again as she gently redirected him toward her bedroom. His steps were wobbly, uneven. The second he walked in, he launched himself belly-down onto the bed, much like he had with the sofa.

Suddenly Penelope became very aware of the fact that Anthony carried a great deal in the back. And none of it had anything to do with responsibility.

She swallowed hard, instantly feeling awful for noticing.

He was her friend’s older brother–drunk, vulnerable, and possibly still engaged. The situation was morally complicated enough without her actively appreciating the view.

His eyes were closed, though he clearly wasn’t asleep. He kept mumbling to himself, words blending together into complete nonsense.

She forced herself to look away and regroup. But first, maybe she could appreciate the view for one second. After all, it wasn’t every day Anthony Bridgerton ended up sprawled in her bed.

Her phone vibrated in her pocket as if reprimanding her for the thought.

Finally Colin and Eloise had replied to her texts, but they were no help. Apparently, the entire family was already at Aubrey Hall for Benedict’s engagement party the following weekend.

Penelope let out a dry chuckle, thinking it must be nice having an entire week off to celebrate. They both told Penelope to let Anthony sleep it off and that he would be better in the morning. It didn’t sound terrible, but it also didn’t feel right. He was clearly in pain, physically and otherwise.

She tossed her phone onto the nightstand and planted her hands on her hips, trying to decide what exactly one did in this situation. She had never been drunk a day in her life, which was probably how she had ended up with the title of designated driver in the first place. 

Penelope approached the bed and gently rolled him onto his back so she could see his face.

“Hey,” she said softly. “Are you alright?”

“I’m really hot,” he muttered. “Need to get out of these clothes.”

He blinked his eyes open and attempted to prop himself up on his elbows first. He then sat up on the bed, and immediately started fumbling with his jacket. Penelope stepped in to help slide it off his arms, wincing when his elbow accidentally bumped into her chest.

His hands moved to the buttons of his shirt, but his coordination had clearly abandoned him. After several failed attempts, he groaned in frustration. Without warning, he ripped his shirt open.

Penelope gasped. That was one way to solve the problem, she thought, unable to move.

He shrugged the ruined shirt off and stood, already fumbling distractedly with his belt. Any effort she made to politely avert her eyes before was long gone.

And judging by the way his mouth twitched, he noticed.

“Well?” He asked, sounding more confident than he looked. “Are you going to help me or just stand there and drool?”

“I’m not drooling,” she shot back quickly. “I’ll be in the living room to give you space.”

“Wait,” he frowned in exaggerated offense. “You can’t leave your own room. This is your room, right?”

“Yes,” she said carefully. “And it’s fine. You need to rest, and I’ll just… work.”

It was a lie of course, she had no intention of working. But it sounded like the kind of argument Anthony might accept.

“Pretty Penne,” he said, lips puckering dramatically, “please don’t go. I don’t want to be alone.”

Penelope exhaled slowly, trying very hard to focus on the practical facts of the situation—not that he was standing in her bedroom looking unfairly attractive and unexpectedly vulnerable.

“I guess I can stay until you fall asleep,” she said finally.

The smile that spread across his face was immediate. 

“You’re perfect. Perfect Penne.” He said, looking at her as if he actually meant it.

She swallowed, trying to not think too much of it. He was clearly drunk, and would probably attempt pairing her new nickname with every adjective that started with the letter P. 

“Would you be so darling and help me with my pants?” He asked in his tipsy voice that gave him a country accent.

Penelope should have said no. But the quicker she put him to bed, the faster he would recover and leave. So she simply nodded and stepped closer, focusing on his belt as she tried to not let her hands shake. She unfastened it carefully, then reached for the button of his slacks.

Anthony shifted his hips slightly, and for a second she felt some of him. Which felt like a lot of him. She wet her lips and shook her head as if that would somehow toss the thought away.

She had never looked at Anthony that way before. 

And it wasn't just because of his current state of undress.

He had always existed in a completely different orbit. Their lives only really overlapped through his family, so it never felt like there was a lot more to explore just between the two of them. 

But now–standing this close, sharing the same warm air, and having spent the last hour alone with him– she wondered if that had actually been true at all.

Thankfully, after helping Anthony get to bed, it didn’t take long for him to fall asleep. 

She was surprised by how quickly he went from chatty, to flirty, to sleepy. Other Bridgertons she had picked up from bars had always been exaggerated versions of themselves—Eloise became extra chatty, Benedict extra flirty, and Colin extra sleepy.

Anthony had been all of them and interestingly, it felt very telling.

Penelope tried to go back to her original plans for the night, but she couldn’t relax. She was too agitated to sleep, so inevitably, she ended up on her laptop doing the one thing she had specifically said she did not want to do on a Friday–work.

Being surprised seemed to be the theme of the night, considering she was suddenly more productive than she had been in weeks.

She barely noticed the hours passing, her fingers moved nonstop across the keyboard. The likelihood that she would later edit, rewrite, and second-guess everything was very real, but for now, she was content to occupy her mind with something other than the entirely new set of mental images she had of Anthony after removing his clothes.

She was deep in concentration when she heard a sleepy voice from the hallway.

“Penelope?”

She looked up from her laptop to find Anthony was standing there, scratching his head and wearing her robe.

It was so short on him it looked more like an oversized silk blazer, doing very little to cover anything—if covering anything had been the intention.

“Hey, you’re awake. How are you feeling?”

“Like I was run over by a truck.” He rubbed his face with both hands.

“Well, considering you’re calling me by name, I can safely say you sound a lot better than when I picked you up.”

He frowned, then winced. “I’m scared to ask what I called you before.”

“Nothing so bad that it couldn’t have been worse,” she teased.

“Mm,” Anthony hummed with a slow smile followed by a yawn. “Reassuring.”

“You don’t seem surprised you’re here,” Penelope observed.

“I already had my five minutes of panic when I woke up,” he admitted, running a hand through his hair. “I’m mostly situated now.”

Penelope chuckled then narrowed her eyes. “What gave away you were in my bedroom?”

“The… pictures on the wall, of course,” he said, clearing his throat as if there was more to it. “Did a…. Did anything happen between us?”

She snorted and denied it quickly. “Obviously not.”

“Obviously? Ouch,” he placed a hand over his chest, pretending she had hurt him.

“Sorry, I don’t sleep with drunk men. I have some standards.” 

“That’s a shame,” he said teasingly. “About us not sleeping together, not your standards.”

She widened her eyes and her thoughts went straight back to his very detailed ramblings of what he wanted to do with her in front of a mirror. The difference being he was drunk then, and now he was mostly sober. And somehow, still flirting with her. So naturally, she had to push it.

“Is that why you got drunk?” she teased. “So I would pick you up and bring you here for us to be alone?”

He smirked at her conclusion. “Now I wish I would have thought of that.”

She shook her head, laughing softly. “I see your flirty mood hasn’t worn off with the alcohol.”

“Because it’s not a mood.” He winked, crossing his arms and leaning his shoulder against the wall. 

Penelope’s breath hitched. Sure, she knew he was what half of her literary references would call a rake, but that was before being in a committed relationship. Unless that was no longer the case as she had suspected.

As much as she liked asking questions, she found a strange peace in not dissecting the situation—just letting him talk if he wanted to.

“If you say so, Sexiest Man Alive.” 

Anthony went pale at her words.

“How did you—” He stopped. “I told you, didn’t I?” He exhaled. 

“Yeah,” she said, trying not to laugh. “You joked about it.” 

“Right, I was joking.” He smiled a little too forcefully, then suspiciously changed the subject. “Do you know what time it is?”

She glanced at the corner of her screen and replied with a sigh. “4:13 a.m.”

He blinked. “You always wake up this early to… work?”

“Not really. I’m not exactly an early riser.”

His brows furrowed. “So you haven’t slept at all?”

“I was feeling inspired,” she defended. “Which doesn’t happen often when I already have two hundred pages written, so I had to seize the moment.”

“Really?” he asked, settling into the chair across from her at the small round dining table. “I thought you would never run out of things to say about female authorship, anonymity, and social constraint in nineteenth-century British literature.”

He said it casually. Far too casually.

Penelope opened her mouth, dumbfounded.

“How do you even know what my dissertation is about?”

“You’ve been writing it for the last two years,” he shrugged. “And talking about it for the last four. Give or take.”

She covered her mouth with one hand, laughing nervously at the realization that he had apparently been paying attention all along. Maybe now that she was 28 and he was pushing 40, their lives no longer belonged on opposite ends of the universe.

And as he looked at her with sleepy eyes and quiet admiration, the distance between them felt smaller than ever.



Notes:

🍸Anthony down bad at the bar fighting olives was almost a better visual than him ripping his shirt off (it wasn't, but you know. Close second)

🍸Penne & Carbonara is a delicious combo 😏🔥

🍸Remember when JB drunkenly told his friends he was Sexiest Man Alive before it came out and they didn't believe him? It was too perfect not to allude to it 🤭 (Pen of course somewhat believes it...)

🍸One of my favorite Penthony micro tropes is when she has no idea he's paying attention to her 🥹

🍸What do you think? I'm kind of curious to see where they could go from here...

🍸Rare Pair Week will be August 2-8, 2026!! Check out the collection for prompts and join us 💜 - 2026 Rare Pair Week