[Modern Family] Ch: 35 [The Million-Dollar Date Night] (Patreon)

AN: Really big ch. 3.3k words. I did my best to edit it properly. And hope you like it.

Dinner was considerably calmer than the rest of their afternoon.

Penny spent most of it asking Jason how he'd managed to stay so relaxed after winning the lottery, especially since she'd barely stopped thinking about the money since leaving the Lottery office. Jason explained how quickly large amounts of money could disappear when someone suddenly started treating every purchase like it no longer mattered. He even told her how he wasted so much of that jackpot after winning it on shoes and watches and other unnecessary things before stopping himself.

He advised her to keep her winnings private, avoid lending large amounts to friends or family, and not to let anyone know how much money she had.

By the time their food was finished, Jason had helped Penny divide the money into four simple categories.

The first portion would remain inside a savings account where she could earn interest while keeping a reliable emergency reserve after paying her credit card debts. The second would become long-term investments, with Jason suggesting that she buy some Apple and Nvidia shares and then forget they existed for ten or fifteen years. If acting didn't work out, the investments could eventually become part of her retirement. If acting did work out, having more money later certainly wouldn't hurt.

The third portion would support her career. Acting classes, professional headshots, transportation to auditions, workshops, and anything else that could genuinely improve her chances instead of forcing her to choose between pursuing acting and paying rent.

The final portion would remain available for normal life. Rent, groceries, car expenses, medical bills, utilities, clothes, and whatever other everyday costs appeared.

Penny didn't pretend to understand every financial detail immediately, although the simple structure made the money feel considerably less overwhelming. For the first time since seeing the winning amount, she could imagine using it without accidentally wasting it all on expensive shoes and handbags. 

By the time they left the restaurant, the conversation about money had finally settled into something manageable.

...

[Restaurant Parking Lot]

The evening air had cooled slightly by the time Jason and Penny reached the Nissan. Lights from the restaurant reflected across the parked cars while traffic moved steadily along the road beyond the lot.

Jason stopped beside the passenger door instead of unlocking it.

Penny noticed immediately.

He'd been relaxed throughout dinner, joking with her between bites and answering every question she threw at him. Now something about his expression had changed. His hands slipped into his pockets, and for the first time that evening, he looked genuinely uncertain about what he wanted to say.

Jason looked at her for a moment before speaking. “I need to tell you something about me. I really like our day and you... and I don't want to lie to you.”

Penny's eyes widened immediately. “Oh my God, you aren't married, are you?”

Jason stared at her for half a second before laughing. “No. I'm definitely not married.”

Penny's shoulders relaxed, though only slightly. Her previous experiences apparently weren't allowing her to stop there. “Wait. You aren't some criminal on the run, are you?”

Jason laughed harder and shook his head. “No criminal record either. At least nothing beyond illegally good-looking behavior, which hasn't been prosecuted yet.”

Penny rolled her eyes, though a small smile appeared. “Okay, rich guy who suddenly gets serious in parking lots after an awesome day. You understand why I'm preparing for something insane, right?”

Jason nodded because she had a point. “Yeah, that's fair. And this might qualify as a little insane.”

Penny's smile weakened. “That's usually not what a girl wants to hear before getting into someone's car.”

Jason drew a slow breath and leaned back against the Nissan. “I'm dating two other women.”

Penny froze.

For several seconds, the sounds of the parking lot seemed to become considerably louder around them.

She stared at him, waiting for the sentence to change somehow.

It didn't.

“You're dating two women?” Penny asked slowly.

Jason nodded. “Yeah.”

Penny's eyebrows climbed higher. “At the same time?”

“Yeah.”

Her expression became increasingly difficult to read. The surprise came first, followed by suspicion and then something that looked dangerously close to irritation.

Penny folded her arms. “And you thought asking me out would be a good idea?”

Jason didn't try joking his way around the question. “I did, because I liked you the moment you entered through those doors in the comic store. That's also why I'm telling you before anything goes further.”

Penny stared at him for another moment before shaking her head. “Wow. Okay. I knew there was gonna be something because nobody has this good of a day without the universe eventually throwing garbage at them.”

Jason gave her a small smile. “That's pretty much why I wanted to tell you now.”

Penny looked away toward the restaurant entrance and released a breath through her nose. “Do these women know about each other?”

Jason answered immediately. “They do.”

That brought her eyes straight back toward him.

“They know?” Penny asked.

Jason nodded. “Both of them know everything, and there's no cheating involved.”

Penny's expression shifted again. The irritation didn't disappear, although some of the accusation behind it weakened.

She studied him carefully. “And they're actually okay with this?”

“They talked about it themselves before we all sat down together,” Jason explained. “There was jealousy and arguing before that because they both liked me, but eventually they decided they wanted to try dating me at the same time.”

Penny blinked several times. “They decided that?”

Jason nodded. “Yeah. I mean, it was their choice in the first place.”

Penny's lips parted slightly as she processed everything.

She had clearly expected the conversation to become much simpler once she discovered the truth. Jason would admit that he was cheating, she would tell him exactly what kind of asshole he was, and then she'd call a cab or make him drive her to her apartment while she spent the entire trip glaring at him.

Instead, he'd somehow made the situation considerably stranger.

Penny rubbed her forehead. “Okay. So you're telling me that you're dating two women, they both know you're dating the other one, and they agreed to keep dating you anyway?”

“That's exactly what I'm telling you.”

She looked at him with complete disbelief. “What kind of women agree to that?”

Jason hesitated.

Penny immediately caught it. “Why did you hesitate?”

Jason's mouth twitched. “Because there's another part that's probably going to make this sound even crazier.”

Penny slowly lowered her hand from her forehead. “Oh, fantastic. Somehow we haven't reached the crazy part yet.”

Jason looked directly at her. “Their names are Haley and Alex. They're sisters.”

Penny looked at him.  

Her mouth opened, then closed, and then opened again.

“You're dating sisters?”

Jason nodded once.

Penny turned away and began walking several steps across the parking space before stopping with both hands on her hips. “Okay, wow. Wow. You really buried the important part there.”

Jason watched her carefully. “I figured saying everything at once might cause some kind of system failure.”

Penny turned around. “You think?”

Jason couldn't stop a small laugh, though he quickly controlled it when Penny's eyes narrowed. “Sorry. Bad timing.”

“Very bad timing,” Penny replied before walking back toward him. “How old are they?”

Jason answered her, then continued before she could immediately jump to another conclusion. “They're both adults, they both know what they're agreeing to, and neither of them was pressured into anything.”

Penny looked unconvinced by the entire universe rather than by that specific answer. “And they seriously sat down and decided sharing a boyfriend sounded easier than choosing which one of them gets you?”

Jason rubbed the back of his neck. “When you phrase it like that, I sound like the prize inside a cereal box.”

“You kinda do right now."

“Fair.”

Penny leaned against the car beside him, leaving several feet between them. For a while, she didn't say anything.

Jason let her think.

That seemed to matter more than trying to sell the arrangement.

Eventually, Penny glanced toward him. “So why tell me? You could have lied like everyone else and enjoyed being with me for a few weeks before leaving me.”

Jason met her eyes. “Because I'm not scum. I like you, and I want to keep seeing you. If that happens, you deserve to know exactly what you're getting involved with before you decide anything.”

Penny looked at his face and saw no smugness or nervousness as he simply told her he wanted multiple girlfriends, which upset her in a different way because it made it harder for her to be angry.

She looked down toward the pavement. “You know what's really annoying?”

Jason shook his head. “Probably several things about me.”

A reluctant smile appeared before she suppressed it. “I've dated guys who lied about being married. Guys who lied about money. Guys who disappeared when things got difficult. One never returned my money and my undies. So when you started this whole speech, I was already preparing myself to find out that you'd been screwing around behind somebody's back.”

Jason remained quiet.

Penny looked at him again. “And instead you're standing here telling me something that could easily make me leave because you don't want me finding out later.”

Jason nodded slowly. “I'd rather you walk away because you know the truth than stay because I hid it. As I said, I'm not scum. And I never lie, unless it comes to how much I eat and never exercise because I never get fat."

That answer landed harder than Penny expected.

She folded her arms again, though there was less defensiveness in the gesture now. “Damn it.”

Jason raised an eyebrow. “What?”

“That was a really good answer.”

He smiled slightly. “I occasionally have those.”

Penny rolled her eyes before looking away. “Don't ruin it.”

Jason chuckled softly and leaned back against the car.

Penny remained quiet for several seconds before curiosity finally started overpowering the initial shock.

“So what happens if you like another woman?” she asked.

Jason considered the question carefully. “Then I'd talk about it before doing anything. The whole arrangement falls apart if people start hiding things.”

“And they can date other guys?"

He barely needed time to think. “Nope.”

Penny blinked. “Nope?”

Jason shook his head with complete certainty. “If you're with me, then you're with me. I'm not interested in sharing the women I love with other guys.”

Penny's eyebrows climbed. “Wow. Okay. That's pretty possessive coming from a guy who's dating two women.”

“I know exactly how it sounds,” Jason replied without trying to dodge the obvious contradiction. “But I'm not gonna lie to you just because the honest answer makes me look selfish.”

Penny folded her arms. “At least you're aware of it.”

Jason smiled slightly. “Very aware. But here's how I see it. When I'm with someone, I'm gonna love her with everything I've got. I'll take care of her, support her, be there when she's having a terrible day, make sure she never feels like she's dealing with everything alone, and do everything I can to keep her happy.”

Penny's teasing expression weakened slightly as she listened.

Jason kept his eyes on hers. “And once you actually fall for me, I don't think you're gonna be sitting around thinking about other guys anyway.”

Penny stared at him for several seconds.

Then a disbelieving laugh escaped her.

“Oh my God.”

Jason's smile widened. “What?”

“That might be the most ridiculously confident thing a man has ever said to me.”

“I warned you I'm confident.”

“No, honey, confidence is asking a girl out five minutes after meeting her,” Penny replied while pointing toward him. “What you just said is confidence after it joined a cult and declared itself emperor.”

Jason laughed. “Okay, that's pretty good.”

Penny shook her head, though she was smiling now. “You seriously think you're gonna love somebody so much that every other man just disappears from her brain?”

Jason shrugged lightly. “That's the goal.”

“The goal?”

“Yeah. Why would I go into a relationship planning to be mediocre?”

That made Penny pause.

Jason continued before she could answer. “If I'm asking someone to accept something this unusual, then I'd better make damn sure she never feels like she got the worse end of the deal. I don't want anyone with me wondering whether I care about her enough or whether she's alone just because I'm spending time with somebody else."

Penny studied him carefully.

That part sounded considerably less arrogant than the first.

“You've actually thought about this.”

“A lot.”

“And Alex and Haley agreed to that?” Penny asked.

Jason nodded. “As I said, once you're with me, you won't be able to think about another guy. And I love them. They love me. That's all there is to it.”

Penny slowly exhaled and looked across the parking lot. “Okay. I don't know whether that's romantic, insane, unfair, or somehow all three at once.”

Jason smiled. “I'll accept all three.”

She looked back toward him. “Of course you will.”

Jason leaned comfortably against the Nissan. “I'm not pretending this is some perfectly balanced philosophical system, Penny. I'm telling you what I want. I'm serious about the women I'm with, and I don't want casual relationships where everybody's halfway looking for somebody better.” His expression softened. “If somebody chooses me, I want her to know I'm choosing her too. Fully.”

She'd dated enough men who'd treated relationships like something temporary, convenient, or disposable. Men who disappeared when things became inconvenient. Men who lied. Men who kept options available while expecting her to remain committed.

Jason's arrangement was bizarre.

Possibly completely insane.

Yet somehow he sounded more serious about commitment than half the supposedly normal men she'd dated. 

Penny rubbed her forehead. “You are making this way harder to reject than it should be.”

Jason's eyebrows rose. “That's encouraging.”

“Don't get excited,” Penny warned, though her smile betrayed her. “You are still currently dating two sisters.”

Jason nodded. “I'm aware.”

“And you're telling me that if I somehow joined this madness, I'd only be dating you.”

“Yep.”

“While you date all of us.”

“Correct.”

Penny stared at him.

Jason stared calmly back.

She finally shook her head and laughed. “The amount of nerve required to say that with a straight face should probably be studied.”

Jason grinned. “Maybe Sheldon can write a paper about it.”

Penny laughed harder at that before catching herself. Then she pointed toward him. “See, this is part of the problem. You tell me something completely ridiculous, then you make me laugh before I can properly get mad.”

“I consider that a useful survival skill.”

“I'm sure you do.”

Her amusement slowly settled, and Penny looked down at the pavement again.

“I still don't know whether I could do it,” she admitted. “Sharing somebody isn't exactly something I've ever imagined wanting."

Jason nodded. “Then don't decide tonight.”

Penny looked back at him.

Jason continued calmly. “I'm not asking you to become my girlfriend right now. I'm telling you what my situation is because I want another date, and I don't want you finding out later and feeling like I tricked you.”

Penny watched him carefully. That honesty remained the part she couldn't dismiss. He told her the truth himself before he kissed her or took her home. He did this before she got too emotionally attached, so the truth wouldn't hurt her.

Penny released a long breath. “I need time.”

Jason nodded immediately. “Take it.”

“And probably several conversations.”

“That's fine.”

“And if I meet Alex and Haley, I want to hear from them directly that they're actually okay with this.”

Jason smiled. “Completely reasonable.”

Penny narrowed her eyes. “Stop agreeing so easily. It's making it difficult to argue with you.”

Jason chuckled. “Should I start being unreasonable?”

“No, because then I'll leave.”

“Then I'll stick with the current strategy.”

Penny shook her head, but another smile appeared. She still thought the entire thing sounded crazy and wasn't remotely ready to call herself Jason's third girlfriend.

Yet she also wasn't ready to walk away.

That realization settled inside her with uncomfortable clarity.

Penny pointed toward the passenger door. “Take me home before your confidence gets any bigger.”

Jason unlocked the Nissan. “So another date is still possible?”

Penny paused with her hand on the door and looked over at him. “Possible,” she said. “Very, very possible.”

Jason's grin appeared immediately.

Penny rolled her eyes. “And wipe that look off your face before I change my mind.”

Jason opened the door for her with exaggerated professionalism. “Absolutely.”

She climbed inside while shaking her head.

Jason closed the door and walked around the car.

Penny watched him through the windshield and couldn’t help but smile. He had two girlfriends. She would’ve laughed at that idea yesterday.

'God, Penny,' she thought, 'you really know how to pick the complicated ones.'

...

...

[Penny's Apartment Building]

Jason pulled the Nissan to the curb and shifted into park. The ride back had been quieter than the rest of their day, although the silence felt comfortable rather than awkward. Penny had spent most of it staring through the passenger window, occasionally glancing toward Jason whenever another thought about their earlier conversation crossed her mind.

Jason turned off the engine and looked toward her. “Well, I guess this is where my extremely normal first date finally ends.”

Penny laughed softly as she unbuckled her seat belt. “Yeah, because winning a million dollars, splitting it with your date, and then admitting you’re dating two sisters is totally normal.”

“When you list everything together, it does sound slightly unusual.”

“Slightly?” Penny asked while giving him an amused look. “Honey, I’m gonna need at least three days before my brain accepts that any of today actually happened.”

Jason smiled as Penny reached for the door handle, though she stopped before opening it. She remained quiet for another moment, then turned toward him with a softer expression.

Before Jason could ask what she was thinking, Penny leaned across the center console and pressed a gentle kiss against his cheek.

Jason froze for half a second.

Penny pulled back with a small smile. “Thank you.”

“For what?” He asked.

“For telling me the truth.” Penny settled back into her seat, watching him for a moment before adding, “I’m still not saying this whole thing isn’t completely insane, because it is. But you told me before anything happened between us, and I appreciate that.”

Jason’s expression softened. “You deserved to know.”

Penny watched him for a moment before her smile returned. “Good. I like honest men.”

Jason leaned back against the seat with a pleased look. “So I got a few plus points in your book?”

“Yeah.” She reached for the door handle. “You definitely earned some points for that.”

“Some?”

“Don’t push it."

Penny opened the door and stepped onto the sidewalk before turning back toward him. She rested one hand against the top of the door while leaning her head into the car.

“And since you asked me out first, the next date is on me.”

Jason looked pleasantly surprised. “So you’re paying?”

Penny’s smile immediately became mischievous.

“Nope.”

Jason stared at her.

Penny laughed as recognition appeared across his face. “Guy asks girl out, guy pays. Girl asks guy out, guy pays.”

Jason leaned back and stared at her like he’d been professionally outmaneuvered. “That feels intentionally misleading.”

Penny grinned. “Welcome to dating me.”

She closed the passenger door and stepped away from the car before turning toward the apartment entrance.

Jason lowered the window. “Good night, Penny.”

She looked back over her shoulder and smiled. “Good night, Jason.”

Penny walked inside the apartment building without looking back again, although the smile remained on her face long after she disappeared through the entrance.

Jason watched the doors close behind her before touching the cheek she’d kissed and letting out a quiet laugh.

"Now, I gotta tell Haley and Alex. Damn, this is gonna be hard.”

He started the Nissan, pulled away from the curb, and drove home.