Based on GG - not my characters.

Question - do some bad words throw this into M rating?

He was walking away. He was walking away!

Her mind was spinning. "Take care of yourself, Mary." That's what he had to say to her? Take care of yourself. He breaks into a safe – full of money and stuff he didn't need – with his dumbass friends, using the key for god's sake, and gets caught and sent to military school. And he tells her to take care of herself. What the hell, she thought. It was so far-fetched, it sounded made up. But no. It was real. And the guy she'd only recently started to tolerate – fine, maybe more than tolerate, if she was being honest with herself – was being sent away.

It felt wrong. She didn't have time to analyze why it felt wrong, but it did. She panicked a little, because he was almost to the guy that had to be his dad. The guy who looked remarkably like him, except with brown spiky hair instead of blonde. The guy who was sending him to military school.

She took off running down the Chilton hallway. "Tristan! Wait!" She felt like an idiot, but she lifted her Juliet skirt to move faster. Skidding to a halt in front of them, she closed her eyes for a second and took a deep breath. She looked up at the older man. "You're his dad?" When he raised an eyebrow and nodded, she pressed on. "I'm Rory. Rory Gilmore. He," she said pointing to Tristan, "calls me Mary, because he's a jackass. Most of his friends are jackasses, but he's become less of a jackass lately." She looked over at Tristan, who was standing there with his hands deep in his pockets, looking at her like she was crazy. "But he's not really like them. His friends. They're bored, lazy, and stupid. He's bored. He's a little lazy. But he's not stupid."

Ben Dugrey tried not to smile at this girl's rant. "I'm aware of that, Ms. Gilmore."

"He makes dumb decisions sometimes."

"I'm aware of that, too."

"This was a dumb decision. But you know - you know - he wasn't going to take anything from that safe."

His dad nodded again. "So why does he have to go to military school? He opened something that wasn't supposed to be opened. He didn't take anything. Actually," she turned to Tristan, "who opened the safe?" At his stare, "Come on, Tristan. Help me out a little here. Did you open it?" He gave a small shake of his head. "Okay, so he was there when someone else opened something that wasn't supposed to be opened. And, he didn't take anything. Aren't there any other options? Can't you ground him? Take away his Range Rover? Make him scrub toilets, or do dishes, or – hey – maybe read a book? Why does he have to go?"

Ben studied her while she made her pitch and waited until she finally lost steam. He ran a Fortune 500 company and made decisions, decisions that affected thousands of people, every day. But this one affected his son. Tristan had been getting into more and more trouble lately – mostly stupid pranks, like this one, but one day it was going to be bigger. Bigger than he could fix. Ben happened to be in town and home when this one happened, unfortunately for Tristan. And he'd made the snap decision that his son needed discipline – the boot camp kind of discipline. But maybe he didn't. Maybe he needed structure. Consistency. God knew, he and his ex-wife hadn't provided either. He'd spent all of Tristan's life working his way up the ranks of Dugrey Global and eventually taking it over when his own dad retired, and he hadn't been home much. And Tristan's mom, well, motherhood wasn't her thing. Tristan had largely been ignored. They'd fucked up. He'd fucked up. Maybe it was time to rectify that.

"Do you like school, Ms. Gilmore?"

She bit her lip. "Yes."

"Are you smart?"

She wrinkled her nose. "I'm number one in our senior class." Ben considered that. His son had sought out one person before he left, and it was the smart girl. Sure, she was pretty, too, and her eyes packed a punch, but this seemed like a change for Tristan. He hadn't been able to hear their exchange a few minutes ago, but he had watched it. The body language made him wonder.

"Okay. You've raised some interesting points. Maybe some valid points. Here's my offer. To you and to Tristan," he said looking at Tristan, too. "Tristan can stay under the following two conditions. First, he has to do better in school. You help him study and stay on him so he stays focused and does the work. Second, you're his babysitter. During the week, he goes to school and comes home. That's it, unless he goes somewhere with you. Same for the weekends. During the weekends, he goes with you on Friday and Saturday nights, or he stays home. You keep him out of trouble. We're only a couple of weeks into the school year. You get him through this semester, and he's off the hook."

Tristan started to talk, but Rory shook her head. "We just need a minute. Excuse us." She grabbed his arm and pulled him down the empty hall.

"So?" she asked him. "What do you think?"

"It's ridiculous. You can't be my babysitter for four months, Rory." He'd almost laughed out loud when he heard his dad's conditions. He was seventeen, and his dad was bargaining for a babysitter for him. Ridiculous.

"You can't go to military school, Tristan."

He leaned back against the lockers and bent forward, running his hands through his already messy hair. Looking at the floor, he said, "I don't know. How bad could it be?"

She fought the urge to reach out to him. "Don't be stupid. You can't go. I have this feeling – if you go, it's going to change you. Change who you're supposed to be. And, while you're a pain in my ass now, I think there's probably some redeeming quality under the cocky bullshit. And it's my time. I can do what I want with it. And I'll do it, if my mom says I can."

Tristan stared at her, processing her explanation. "Your boyfriend is going to love this."

She shrugged her shoulders. Dean hadn't even crossed her mind. She pushed that issue aside for now. It wasn't a deal breaker for her. She crossed her arms across her chest and smiled at him. "Come on, Dugrey. Say yes. You're going to be my bitch for four months."

At that, he laughed and pushed off the locker. "Okay." He reached out and offered her his hand. They shook on it, grinning at each other. "Come on, Mary. Let's go make our deal with the devil."

"Satan. If you're the spawn of Satan, he's Satan."

Paris intercepted him to get dressed as Romeo before they reached his dad. "Go on," Rory told him. "I've got this."

He leaned down to whisper in her ear. "Get ready to pucker up, Juliet." He was gone before she could roll her eyes.

She held up her finger to Mr. Dugrey, asking him to wait one minute, and trudged off down the hallway to where her mom and grandparents were waiting.

She pulled her mom away, after asking her grandparents to stay for a second. "So, Tristan – Bible Boy, Spawn of Satan, the guy I was just talking to?" Her mom nodded. "He got in trouble for some dumb prank, and his dad, the other guy down the hall," she said pointing to him, "is threatening to send him to military school. His dad says he can stay, if I help him study and, as he put it, babysit him so he doesn't get into more trouble." Rory looked at her mom. "We have the same classes, so it's just staying on him to do stuff, and I'd have to hang out with him some. Not that big of a deal. I want to do this. But I need you to be okay with it."

Lorelai was a little lost. Everything she'd heard about this kid had been negative. He drove Rory nuts. Didn't he? "I don't know, honey. I love that you want to help someone, but it sounds like a lot. You're going to be able to keep the Spawn of Satan out of trouble? What if you can't? What if you can't get your work done?"

"He's got to conform to my life, not the other way around. We'll be studying and doing what I do, so he'll have to deal with it. I think his dad wants my nerd-ways to rub off on him."

Lorelai still felt like she was missing something here. "Where do grandma and grandpa come in?"

"He stays home unless I'm with him. So, I'm guessing I'll be dragging him to Friday night dinners sometimes."

"Oh boy," Lorelai laughed. "Tell him about those; he might choose military school." Rory stared at her. "Okay, kiddo. You really want to do this?" Rory nodded emphatically. "Then we'll give it a whirl. If it doesn't work, you'll know you tried." Rory hugged her mom. She gave her grandparents a less detailed version of the story. They were happy to have Rory's friend come to dinner as often as he liked.

Rory brought her mom down to meet Tristan's dad. "Mr. Dugrey, this is my mom, Lorelai Gilmore." Ben knew of Lorelai, but he had never met her. He'd connected Rory to Richard and Emily, but not to Lorelai for some reason. He shook her hand. She was an older version of Rory – pretty, same eyes – younger than him, probably by five or six years doing the mental math of what he'd heard about her pregnancy and Rory's birth. And he could tell she was not thrilled with this situation.

Rory jumped in. "Tristan had to go get dressed for the play. But we agree. My mom has agreed, less willingly, and you two can talk about that if you want. My grandparents have agreed Tristan can come with us on Fridays. My mom and I have dinner with them most Friday nights, so I guess Tristan comes now too." Ben listened. "One thing. Tristan and I have a friend. Paris Gellar. She's super smart. I want to be able to punt to her, if I've got a conflict or need help."

"Sure. I've actually met Ms. Gellar. Maybe I should sub you out for her. That'd really punish Tristan." Rory snorted.

"Maybe I can fake an injury for a week and stick him with Paris." Ben smiled, liking Rory. "I've got to go finish getting ready for the play before Paris goes on the war path. Thank you for letting him stay, Mr. Dugrey."

Ben and Lorelai watched her walk away. Lorelai turned to him and dove in headfirst. "I don't understand this situation enough to fully comment, but I'm uncomfortable at the huge responsibility you – someone I just met – have dumped on Rory's head." She raised her hand when he opened his mouth to speak. "I know she agreed to it, and I saw her run over here, so I'm guessing she kind of asked for it. But she's seventeen, and on track for college and whatever else she wants. She's worked hard for it. I won't risk that. If I see this affecting her, I'm pulling the plug."

"Fair enough." He paused. "Look, your daughter seems responsible and smart and, like you said, on track. I'm no expert on teenagers, obviously, but it seems like a good thing for Tristan if he spends his free time with someone like her instead of his idiot friends. He can hang around someone who is a good influence on him, or he can stay home. That's all I'm looking for here." Lorelai nodded, somewhat mollified.

Hours later, Rory was in bed contemplating the strange turn of events that night. She now had a babysitting gig and a Range Rover. Tristan had texted on the way home from the play – his dad was having the SUV, just like the one Tristan drove, delivered to their house before school tomorrow morning. His dad didn't like that she'd be waiting for the bus at odd hours. She'd given him her mom's number so their parents could talk about it, assuming – correctly – that Lorelai wouldn't be happy with that. But they'd ironed it out, and Lorelai eventually caved, with Tristan's dad arguing that Rory could make up some of the time she'd be spending with Tristan on school work if she didn't have to wait on the bus. The car was hers to use for the next little while.

And the play! She smiled thinking about it. It was good Dean had decided to pass on the play because he would not have been happy. Tristan had played his role up, much to the delight of the audience, waving his arms about dramatically. Rory told him afterwards she thought he looked like he was having a seizure. But he'd leaned over her and from the side that showed to the audience, everything was perfectly proper. On the side to the back wall, where nobody could see, his hand roamed around until he found the spot on her side that was ticklish. It was all Rory could do to stay still and act dead. When he proclaimed "Thy drugs are quick. Thus with a kiss I die," she used her hidden left hand to pinch him as soon as his mouth was over hers. He jolted and leaned onto her more, leaving his mouth on hers longer than necessary, but otherwise held it together enough for the scene to end. When he felt her shaking from laughter under him, he whispered, "You're an ass," and pushed off her.