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Drive Me Crazy

Summary:

A charity golf tournament could land Penelope Featherington the publishing job of her dreams, and Anthony Bridgerton just might be the connection she’s been missing.

Day 7: 🃏 Wild Card | 2026 Rare Pair Week
*Pen/Anthony HEA - If you don't like this ship, just skip.*

Notes:

This was the first story I plotted for Rare Pair Week and I was way too excited about all the golf puns. Enjoy!!

Happy birthday @push4champagne!! You are so loved and missed ❤️ Wishing your new year is a lot less busy and you come back to us soon!

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

Work Text:

Drive-Me-Crazy

When Penelope Featherington asked Anthony if she could be in a foursome with him, Simon, and Michael, he immediately agreed.

The Bridgerton Foundation’s Ninth Annual Charity Golf Tournament was just around the corner, which Anthony would describe as a ‘prime networking opportunity disguised as a fundraiser with a side of country club leisure.’

Of course he cared about the causes the foundation supported, but he had been a CEO long enough to know what corporate executives in crisp white polo shirts and old-money board members with customized golf carts were like. They treated the fairway like an extension of their boardrooms, one where drinking gin and tonic before noon was a part of doing business.

As a long-time foundation volunteer and family friend, Penelope knew that just as well.

And it was precisely the reason she was sitting across from him in his office.

“Done.” Anthony clasped his hands together on top of his desk.

“Excellent.” Penelope smiled. “I knew you’d support me. Getting this job would be a game changer for me. No pun intended,” she added shyly.

He smirked behind his coffee cup. People asked him for favors all the time, but for some reason, Penelope asking didn’t bother him nearly as much. Maybe because he knew she put in the work and wasn’t simply looking for a free ride. In fact, he was a little annoyed that she had no interest in working for Bridgerton Corp and was instead going to extraordinary lengths to land a position at Hastings + Kilmartin.

“I’m happy to help you network.” Anthony smiled politely. “…You golf, then?”

The question was followed by a deafening silence. Penelope twirled a curl around her finger and pursed her lips, and he immediately felt a pit form in his stomach.

“…Penelope.”

“I’ve played golf before, yes.” She finally replied.

Anthony slowly lowered his coffee and studied her expression.

“You’ve played golf,” he repeated carefully.

“Beginner,” she clarified, clearing her throat.

He raised a brow, not convinced, and she brushed aside his look.

“Some might call it ‘miniature,’ but that’s just offensive, if you ask me.”

“You’re joking, right?” He chuckled, but Penelope didn’t.

“What? It’s more… my size.”

He opened his mouth, then closed it again. Unhelpfully, his mind briefly questioned whether she had meant golf at all when she asked to be in a foursome with them. Even more unhelpfully, his mind decided it was a good time to wonder which position he would prefer if that were the case.

He blinked and shook the thought away, moving the conversation along.

“Alright. Do you know how long we have until the tournament?” Anthony raised a brow.

“Six days, give or take?” She closed one eye in exaggerated thought.

“Exactly. You’re going to need lessons.” He stared at her.

“Great,” she said, relieved. “I was really hoping you would say that.”

“All right. I’ll ask Edwina to reach out to you for your availability and schedule some sessions this week.”

“I’m wide open,” Penelope replied right away with an eager smile. “Extremely flexible.”

Anthony cleared his throat, tilting his head from side to side. It was a perfectly acceptable way to speak of one’s schedule, so Anthony was not sure why his brain was behaving like a green boy instead of the respectable 36-year-old man he was. He tried to hide his reaction by avoiding eye contact with her, but shifting his focus to the neckline of her blouse was not the escape he needed.

It only made things worse.

Because now he couldn’t move his eyes at all, and it would take less than a second for her to realize what he was staring at. 

He had to recover quickly.

“Flexibility and being open are good,” he finally managed, trying not to wince at his choice of words.

Luckily for him, she seemed too anxious about the whole thing to pay full attention to what he was saying.

“I mean, I would prefer having a job instead of all this free time, but sure.” Penelope shrugged. “It’s kind of depressing doing all that schooling only to be in a limbo of plant sitting and involuntary freelance work.”

He blinked, surprised that she had opened up to him out of nowhere, but in a way, also quietly glad. He only felt bad that his imagination happened to be running wild when she did.

“First of all, you’re not in a limbo. You know what you want to do, and you are actively searching for it. That counts,” he offered, trying to make her feel better.

“Not for my bank account, sadly.” She sighed. “Sorry, I didn’t mean to dump all of this on you. You’re already helping me so much, and I shouldn’t complain. I just thought that after all that hard work, I would have something lined up after graduation.”

“Hey, it’s okay to be disappointed when things don’t turn out how you expected.” He said it with a soft smile. “And it’s even more than okay to share it with me.”

“Thank you, Ant.” She pursed her lips and smiled back. “You’re the best. I have no idea why Colin and Eloise complain so much about you.” Penelope added with a playful grin.

He nodded with a chuckle. “I can’t think of anything, either.”

“I should let you get back to work. Thanks again for seeing me last minute,” she said, rising from her chair. “I’ll stop by Edwina’s desk on my way out.”

He simply smiled and nodded again as he watched her turn and leave. He had a feeling that what had started as a simple favor had just become considerably more complicated.

—

Penelope was on her way to her first golf lesson. She should have been more nervous about having to learn golf in only three sessions before the tournament on Saturday, but she was actually looking forward to the crash course. She had been setting a lot of personal goals lately with the requisite retail therapy, which included a variety of new workout dresses. While she had originally bought them with plans to join Eloise and Phillip on the tennis court, after a very thorough Pinterest search, she deemed the dresses good enough to play golf in as well.

When she got out of the car, she was not expecting to see Anthony. 

Or the apparent disapproval look on his face when he looked at her outfit.

She found him waiting in the parking lot, looking particularly preppy with his hair styled back, navy polo, and tan trousers, leaning against his very new and expensive car. Penelope honestly couldn’t tell if it was a McLaren or an Aston Martin, but she had affectionately nicknamed the car Green Goblin, since its emerald green color made Anthony look more playful and mischievous than he usually let on.

Not that any of this color analysis was ever going to be helpful in her everyday life.

It was just something her mind did.

Anthony kept staring at her, and the thought that there was something wrong with the way she was dressed persisted. She wasn’t trying to offend him or his country club. She simply felt really good in the short, flowy skirt and was proud of her thick thighs and shapely legs, which usually got overlooked by her neckline. Understandably. 

But, in hindsight, she might have worn something else if she had known he was going to be there.

“Anthony? What are you doing here?” She asked as she walked towards him.

He furrowed his brows. “Same reason as you, I hope.”

“Right.” She giggled softly. “Like you need to brush up on your skills before the tournament.”

“I don’t, but teaching you how to golf will be a good warm-up.”

Penelope blinked, suddenly very confused. “You’re teaching me?”

He pretended to look around before looking back at her. “Do you see anyone else joining us?”

“Anthony!” She let out a disbelieving laugh.

“I thought we had agreed on this,” he said, now the one who was confused. “You said you were hoping I was going to offer practice lessons.”

“Yes, but...” Her brain took a moment to catch up. “I thought you were hooking me up with someone you knew. I didn’t expect you to be the one teaching me.”

“Why would I pay for someone to spend one-on-one time with you?” He snickered, then quickly amended, “I mean, teach you how to golf?”

She raised a brow. “Because you’re the busiest person on the planet and you could hire literally anyone you wanted to do it?”

“Hey.” He seemed genuinely shocked by her assumption. “I don’t outsource everything.”

“That’s not what I...” She looked away. “Never mind. It is kind of what crossed my mind.”

She was being self-conscious, and she hated it. She had spent years overcoming her insecurities and self-doubt. Anthony in semi-casual clothes, wearing a new cologne, and making time out of his busy schedule to help her should make her feel like a million bucks, not turn her into a mess.

“Well,” he said, shaking his head with a small smile. “You might be the first person to be offended that I showed up to a commitment instead of sending someone else in my place.”

“I promise this is me just being surprised.” She offered him a smile. “And a little... flattered.”

“Good.” He nodded, pushing himself off the car. “Let’s get started, then.”

–

The first lesson went somewhat worse than Anthony anticipated. It wasn’t that Penelope was awful or anything, more that he was terribly distracted by every move she made. Ever since she left his office the day she asked for his help, he couldn’t get her off his mind.

Later on that same day, she sent him her résumé for his feedback, and one formatting suggestion turned into a whole conversation about her last internship, how they both spoke Italian, and how she preferred pie charts over bar charts, which inevitably led to their first documented argument.

For a moment, it crossed Anthony’s mind how much easier dating would be if only people had the chance to look at each other’s résumé and ask interview questions. He filed the thought away to discuss with his mother. Violet had a knack for matchmaking and could probably make a profit from a dating model like that.

He was not trying to date Penelope, per se. It was only that getting to know her better this way was giving him... ideas.

Business-related ones, of course.

He was trying to keep a respectable distance and stick to verbal instruction, but that was proving ineffective. Unlike when he taught other people, he never once thought Penelope didn’t have what it took to succeed, even though she kept failing to hit the ball in any productive way.

Anthony was beginning to think the problem was him and his method, and he rarely admitted when it was something he was doing that wasn't working.

“Okay now,” Penelope cleared her throat as she adjusted her stance. “All or nothing.”

She swung the club, barely hitting the ball hard enough to get it airborne.

Anthony winced. “I’m really hoping that was your ‘nothing,’ not your ‘all.’”

He tried to be encouraging, but it was not in his nature to lie just to make someone feel better.

“Hilarious.” She groaned.

“It’s not... awful. You’re getting better, one stroke at a time.”

“I feel like I have to cross a whole ocean to make a tiny bit of progress.” She sighed.

“You can’t expect to master something new in one lesson.”

“But that’s who I am... that’s a bullet point on my résumé, remember? I’m a quick learner.”

“Let’s try something else, then,” Anthony said, walking around Penelope.

He stopped behind her, and she pushed her hips out slightly to get into position. Not exactly the one he had been thinking about since she stepped out of the car wearing that short dress and her hair up in a ponytail, unfortunately.

Anthony covered her hands with his, curling his fingers around hers to adjust her grip.

“You’re holding it too tight,” he murmured. “The right pressure matters. You want to be firm enough to hold a tube of toothpaste, yet gentle enough that nothing… squeezes out.”

She cleared her throat. “I can see why that would be bad, yes.”

“When you tighten your grip to try to crush the ball, the tension travels up your forearms into your shoulders,” he explained, moving his hands up her arms to her shoulders to demonstrate, “you’re actually creating a rigid swing that reduces speed.”

“Mm. Who knew there was so much... physiology in golf?” Penelope said lightly, rolling her shoulders back.

“Think about how your whole body is part of it.” He chuckled softly and started massaging her. “And my knowledge comes with years of experience.”

”I’ll bet,” she murmured, closing her eyes and relaxing into his touch.

“Your ball flight issue is more about your grip position than swing mechanics.” He leaned down, getting closer to her temple. “Looser pressure enables a more natural release.”

“Oh.” She gasped, then turned around to face him. “That’s really... enlightening. I think we made enough progress for today, don’t you think?”

“Yes, yes… of course.” He cleared his throat. “You did good, Penelope.”

“Well,” Penelope tried to hide a squeal with a dry laugh. “You’re good too… as a teacher.”

“Happy to know it’s been helpful.” He smirked. “Same time tomorrow?”

“Yes, sir.” She said it playfully, saluting him.

—

By the second lesson, Penelope wasn’t as flustered by the proximity or every accidental innuendo he murmured into her ear. She even started playing along, throwing in her own wordplay to get back at him, and she found herself ridiculously satisfied whenever she managed to get a reaction out of him.

By the third lesson, she was showing solid improvement, and Anthony became even more invested. She could tell by the ridiculous amount of advice he was giving her and the way he insisted she was ready to learn more. Penelope made jokes about his seriousness, and he seemed to enjoy making her laugh.

They soon found that even though Penelope was awful at driving and maybe decent at chipping, she was pretty good at putting. 

The fourth lesson was not part of their original schedule, but Anthony had suggested it so they kept building on her newly acquired skills.

He was baffled when she started sinking one putt after another with zero input from him.

“How are you doing that?”

“It’s just me, the ball, and the hole.” She tried to shrug it off. “And this part is actually very close to mini golf.”

“I’m impressed.”

“I don’t know, maybe save compliments for Saturday.” Penelope gave a small smile and effortlessly putted another ball. “All that matters is how well I perform under pressure, right?”

“And you’re going to be great.” He reassured her. “Do you know how many times I’ve played golf with my siblings?”

“I’m going to guess... not a lot?”

“Precisely. They did not last. You stuck around and pushed through,” he said with conviction. “Trust me, that alone will get you an interview. Simon and Michael will already be fascinated that you can keep up with me.”

“Anthony... I have to tell you something.” She said it with a hint of play, but it still made both his eyebrows shoot up. “You’re not as scary as you think you are.”

“Blimey.” He looked away and let out a soft laugh. “I have a reputation to uphold, you know.”

“Your secret is safe with me.” She smirked back, then pursed her lips in thought. “I... I don’t want to mess this up. This networking thing.”

“Yeah, networking.” He scratched the back of his neck, then folded his arms. “So, why don’t you practice with me?”

“You?”

“I’m the perfect person to practice on.”

She smiled, looking down at her feet and folding her arms too. “It’s not so much about confidence, I guess. I know I can be clever and funny, but somehow, it all gets lost between my head and my mouth, and I end up saying the wrong thing or, more likely, nothing at all.”

“That’s not true. Well, you are clever and funny, not the rest. You definitely know how to carry great conversations.”

“With you, maybe.” Penelope sighed. “Not so much with people who can decide whether I get a job.”

“Which I’m slightly offended by, by the way,” he teased her.

“Why? Because I haven’t applied to work for you?”

“Obviously.”

Penelope chuckled, trying to come up with a more plausible excuse than the truth she was slowly accepting herself: Being around Anthony every day had a high probability of corralling her heart. Seeing him that week and keeping it mostly professional was already challenging enough.

“Last time I checked, you didn’t have a publishing division.” She cleared her throat.

“Not yet. You think it’s a good business to be in?”

“Why?” Penelope raised a brow. “Are you going to open one so I can work for you?”

“Why not? Bridgerton Books has a nice ring to it, don’t you think?”

She let out a disbelieving laugh. He was being ridiculous, she knew, but at the same time, she had the strange feeling that it was exactly the sort of impossible length Anthony would go to.

“Yeah, it’s perfect, actually.” She played along.

“It’s done, then,” he joked. “Though you should still work for Hastings + Kilmartin while I get the paperwork together to get insider information.”

Penelope snorted, and they both laughed. She still half-believed he was being serious, though.

“Okay, boss. How do I land that job, then?”

“Rule number one: don’t tell them what you think they want to hear.”

“Isn’t that what interviews are for?”

“No. For Simon, interviews are for figuring out whether you can do the job. He wants short, clear answers right away,” Anthony explained. “Michael is more like... the culture champion. He will care more about how you will fit in with the team and your working relationship, especially since he would be your direct supervisor.”

“That’s really good insight, thank you.” She nodded and mentally took notes, then whispered jokingly, “But it’s also kind of telling them what they want to hear.”

Anthony shook his head with a soft chuckle. “See? You’ve got this.”

She smiled in response, and in that moment, she thought that there was something special about Anthony Bridgerton having full confidence in her.

—

Penelope was not sure what she expected from being in a foursome with three top executives of multi-billion-dollar companies, but it was definitely not a sword-measuring contest. Every little thing became a competition, which worked out nicely for her. Instead of having to fight for a job, it felt like they were fighting over her.

Anthony was attentive and made sure she was part of the conversation, casually dropping questions that would not only encourage her to share her professional background in a natural way to gain visibility with Simon, but also showcase her humor and wit for Michael.

By lunch, the two extended an invitation for an interview the following week, which Penelope quickly accepted. She was happy with the outcome, but also slightly disappointed that she was running out of excuses to continue to hang out with Anthony.

At the end of the event, Anthony offered to take her home. Luckily, she had carpooled with Eloise and Phillip. She wanted to thank him properly away from the distractions, plus she’d been waiting for the opportunity to ride in the Green Goblin.

“Congratulations,” Anthony said as they both settled into the car. “I told you they were going to love you.”

Penelope looked at him, mesmerized by the way he ran his fingers through his hair, imagining it was her own. She almost reached for it, but held herself back.

“I couldn’t have done it without your help.” She cleared her throat, looking away.

“You could have, but I’m selfishly glad you didn’t.”

“You know, you’re a surprisingly good teacher.”

“Did you ever doubt it? I’m excellent at everything.” He teased her.

“Especially being humble.” She teased back and he smiled. 

“So, same time tomorrow?”

“For golf?” Penelope looked at him.

“Well, your putting is annoyingly better than mine,” Anthony smirked, then paused. “But I just want to spend more time with you. Golf optional.”

“I’d like that.”

Anthony reached out for her hand over the console, and she took it.




Notes:

⛳They are crazy and sweet, and I hope they put all of their unhinged thoughts into practice 😏

⛳Thanks @cmrr95 for beta-ing and not letting me delete everything 🫶

⛳Celebrating my #40 Penthony fic (and 76 overall)!! 🤯🥹❤️🥰👀 Thank you so much for your wonderful support. When I posted my first story almost two years ago, I had no idea I'd still be here. Your kudos and comments are truly inspiring ✨

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