AN: Dates part 2, as promised. Nothing else to add. Enjoy.

Will and Anna sat through the credits after the movie, still holding hands with a half full tub of popcorn on his lap. He'd only made plans as far as dinner and a movie, trying to keep it low key enough not to feel immense pressure. He felt that they could easily make it through both, still having a good time, no matter what. He now found himself wishing he'd planned a lot more, so he wouldn't have to take her back so soon. The lights bumped up and she cleared her throat.

"We should probably get going," she said, causing him to grab the tub with his free hand.

"Yeah, I guess they'd frown on us sitting through another showing for free."

"I'd frown on us sitting through another showing," she commented.

"Yeah, not going to win an Oscar anytime soon, huh?"

"Definitely not."

He let go of her hand, as they both needed to pull on coats. He threw the tub away, and she moved next to him in the hallway. He opened the door for her, and they wandered out into the parking lot. It'd begun lightly snowing, and there was a definite chill in the air. Once she was in the car, he walked around to the driver's side, enjoying the cold winter air for a moment before joining her. He drove back to his apartment, and they got out, standing for a moment in the parking lot. He noted that Dave's car wasn't back yet. He turned to Anna, who was reaching for her car keys.

"I had a really good time," she said, now that she had her cold keys in her hands.

"I don't think Dave's here, if you want to come up for a minute."

She looked around to see he was right, and nodded. "Okay. I'd like that," she smiled, and he took her hand as he led her up to the door.

&&&&

Jess and Gwen had met at the restaurant, she'd insisted on it. She said a first date wasn't the time to make him meet her crazy sister and her family. He laughed, and said his family had the corner on 'crazy'. He walked her out to her car afterwards, and they stood there, lingering for a few moments.

"Thanks for dinner," she said, "Especially considering the circumstances," she added.

"Well, thanks for sticking around through the entire meal," he retorted.

"You're doing fine, I promise."

"Oh, yeah?"

"Yeah," she smiled, looking at him in the eyes.

"Do you want to go get some coffee somewhere," he asked, not quite ready to get back to reality.

"Are you sure?"

"Hey, it's just coffee, right?"

"Right, okay."

"Great, come on, we can take my car. I'll bring you back later."

She smiled at him, and took his outstretched arm as he led her off to his car.

&&&&

"IN YOUR FACES!"

"BOYS SUCK! GIRLS RULE!"

"Okay, kids, did no one teach you about winning with grace?"

"Na-na-na-na!"

"Evidently not," Rory said under her breath. The girls' third straight victory in a row over the boys was cause for great celebration. After the first game, Ambrose had declared it a fluke. This enraged all the teenage girls, who then agreed to make it a best of out of five tournament. Rory and Tristan exchanged knowing glances, as they knew how this was going to unfold. Rory and Ella had simply just seen more movies than anyone else in the room. Jake saw a lot, but he read in his room a lot during movie marathons. They were seen as a girls' night activity, as Tristan often took Jake out to places like batting cages when they did boys' night. Billy's family never really did the watch a ton of movies thing, unless they were with Lorelai, and Ambrose really could clean up in a literary game—which he commented after the second win. To which he was met with three tongues stuck out at him. And now, upon the sealing of the victory, the girls were prancing about the room, rubbing it in. Except Jane of course, who was bored and rolling her eyes, still curled up in her armchair.

"Okay, bed time!" Tristan announced.

"Dad!" Ella protested. "It's only like 10:30!"

"And I'm exhausted. I'm taking your mother with me, and therefore there will be no adult supervision. So, to your rooms, please!"

"Tris, come on," Rory said before yawning.

"Hah, see, you're tired too," he laughed.

"We don't actually have to go to bed," Jake said, looking at his dad.

"No, but boys to Will's old room, and girls get the living room. Chop, chop," he said, gesturing to the separate directions.

With that, Billy, Jake, and Ambrose headed off towards the kitchen while Lia, Ella, Jane, and Jules all moved sleeping bags around the room.

"Hey, Rory, do you have your alarm set?" Jane asked.

"Yes, Jane. We'll get you to the airport on time."

"Oh, good. Mom said that you were very punctual."

"Well, how sweet of her," she mused.

"Oh, wait. You're coming with us," Tristan said, grabbing his daughter's wrist and leading her up the stairs.

"Daddy, hey, slow down," she complained as Rory smiled and followed the two.

&&&&

Will moved around the kitchen, while Anna sat down on the couch. She looked around, not quite sure what to do with herself. This whole prospect of dating her best friend meant she suddenly became unsure in familiar surroundings. Normally, she'd flip on the television, or grab herself something to drink. She'd spent the night on this couch more times than she could count, but now—now she was a girlfriend, awaiting instruction.

"You want something to drink?"

"Oh, sure. I can get it, though," she said, beginning to stand.

"Nah, I got it, relax," he smiled, coming to hand her a soda. He sat down next to her on the couch, and sat his unopened soda on the coffee table. He leaned back and put his arm over the back of the couch. He leaned closer to her, to see if she'd meet him halfway. She gave him a coy smile, and then leaned closer as well. He kissed her softly, and he felt her scoot closer in towards him. He let his arm come down from the couch and move around her shoulders. She pulled back a little, and they looked into each other's eyes. He smiled and moved in to kiss her again, a little less hesitantly this time.

And it was like this that Davey found them. He had seen her car and Will's both in the lot, and made as little noise as possible upon entering the apartment. He breathed a sigh of relief when he found them in the living room, but the weirdness factor of seeing his best friend and sister (for the first time) kissing like that—he cleared his throat to make it stop. The two immediately ceased kissing and looked at him. Anna smiled and looked down, and Will stood.

"Hey, you're back."

"Yep. I'm back."

"How was your date?"

"Good. It was good."

"Good."

"I'm going to go, I should get home," Anna said, standing now next to Will. She leaned towards him, and he moved to hug her. She pecked his cheek, and he awkwardly did the same as they pulled out of the hug. She smacked her brother on the bicep as she walked past him, and gave Will one last smile as she exited the apartment.

"So, your date went well, too, huh?"

"Yeah, it did," Will smiled.

"You weren't about to take her back to your room were you?"

"What? No, I wasn't."

"Because she's been through a lot lately. She doesn't need that kind of pressure," Dave warned.

"Oh my God. You're kidding me, right?"

"What?"

"Dave, this is me. How long have you known me?"

"All your life."

"Right. And suddenly because I'm dating your sister you think I'm some careless prick that's just out to do her?"

"No! I'm just saying," Dave started.

"I know what she's been through! She told me first, and I was there for her, through all of it. I'm not going to pressure her to do anything, and you should know that."

"I do. I'm just concerned about her. And you," he added.

"Me?"

"You, dumbass. You've been through a lot. Whether or not you realize it, Bree screwed you up really badly. You were in love with her for like four years, Will. You were going to marry her—you don't just get over that lightly."

"So?"

"So, you need to take this slow as much as Anna does."

"Oh. Right," he said, scratching the back of his head. "Thanks, Dave."

"No problem. I'm beat, I'm going to bed."

"Yeah, me too. Night."

"Night," he said, patting Will's back as he moved past him down the hall into his bedroom.

&&&&

Jess sat drinking coffee with Gwen for two hours. He'd never been bad at the dating—some women made it more tolerable of course, and she was one of those women. If he were free, with no responsibilities to anyone else, he'd have stayed out all night with this woman, easily falling into what once had been his good first date activities. And he would have had a damn fine time showing her a damn fine time.

But he had kids, waiting back at Rory's house. He had a wife that should they later decide to get back together, he wouldn't be able to lie to. And should they not end up together, he wouldn't want it any other way either.

So, when she smiled at him after her third cup of coffee, he knew he had to tell her this.

"I'm having a great time," he said in a tone of voice that made her sure it was a precursor to some other topic.

"But?"

"But, I think I need to call it a night now."

"Ah, right."

"And I don't think I should see you again until we get back to New York."

"Oh. Okay," she said, frowning as she looked into her empty coffee cup. "May I ask why?"

"Because, I'm having a really good time with you."

"Is it okay for me to be really confused?"

"I have to take care of my life before I can drag you into it; I don't want to encourage you when I don't know if I can," he explained.

"My, my, someone is full of himself, isn't he?" she teased.

"Am I being presumptuous?"

"Well, yes, but correctly. I like you, too, Jess. And I'd be lying if I said I didn't wish you had all this behind you, but," she sighed, "I understand."

"Good," he said, taking his last sip of coffee.

"So, we should go," she said, with more than an air of disappointment in her voice.

Once they got back to her car, he got out to say goodbye to her. He hugged her, and leaned his mouth down to her ear. "Thanks for being as disappointed as I am," he said, kissing her cheek as he pulled away from her.

"No problem," she said, nodding. "Call me when you get back to New York," she said, putting a piece of paper in his hands. It was her business card.

"I will. I promise."

She nodded again, and then got into her car. He watched her drive off and shuffled his feet all the way back to his car. He needed to call Erin. Take a long shower, and call Erin.

&&&&

Lorelai lay in Luke's arms, and buried her face in his chest.

"That was the hardest thing I've ever had to do!"

"But you did it, that is the important thing."

"She looked so hopeful, and I just lied. I lied to my best friend."

"You omitted details, you didn't technically lie."

"Oh, please. If I omit details with you, you call it lying."

"Well, I'm your husband, that's different. And you did this for your son."

"So? I've known Sookie way longer!"

"Just, go to sleep, I beg you," he tried, holding her a little snugger.

"What? I've been a bad girl, and I don't even get to have the fun of being a bad girl? The universe hates me," she declared.

"I didn't realize you were up for that, you keep ranting about what a bad person you are."

"Oh, Luke, when have I not been up for that?"

He thought about this for a moment, couldn't for the life of him remember a time that she wasn't willing to have sex. Good moods, sad moods, bad moods—actually the worse the mood she started in, the better and more interesting the sex. He moved her on her back in one motion, causing her to emit a little squeal.

"You're right. Let's go."

"You do love me," she sighed happily, melting under him.

&&&&

Ella sat on her grandmother's bed, as her father slumped into a chair. Her mother was leaning back against the dresser, and they both had very different expressions on their faces.

"So, is this an interrogation?" she joked.

"No," her mother assured her.

"That depends," her father piped in at the same time. Rory shot Tristan a look, and he held up his hands.

"I'm kidding."

"We just wanted to hear about your weekend. What did you think of the schools?"

"They were great. It was a fun weekend."

"Ella, college isn't going to be all about fun. Your father and I want you to have a good time, but it's," she began before Ella cut her off.

"You didn't ask specifically about the academic stuff. We got really good tours, except at Princeton where they sort of meshed us together. But both Yale and Sarah Lawrence gave us really specific tours to what we were interested in. Both had excellent journalism schools, and right now it's a real toss up. Both have great professors, interesting programs and will prepare me for top graduate programs."

Rory looked to Tristan, and smiled. He smiled back.

"So, it's one of those two?"

"Yeah, I think so. But I have plenty of time to decide. Unless Sarah Lawrence comes back with a no. They all but handed me my acceptance letter at Yale," she told them.

"So, what are your deciding factors?" Tristan asked.

"Well, at Sarah Lawrence I could come home whenever I needed, easily. At Yale, I'd be close to Grandma, and Billy," she said. A look of surprise covered both their faces.

Before Tristan could say anything, Rory moved in front of him. "So, Billy is a consideration?"

Ella looked down at her hands, and shrugged. "Maybe."

"Wow. We didn't realize, I mean, when did this become serious?"

"It's not really serious, yet," she assured them. "But it might be, by then."

"You're only seventeen," he father reminded. Rory nodded in agreement, glad he was being level headed about their baby girl telling them she was willing to base her future off of a boy she'd been dating just three weeks.

"But I've known him forever."

"Yeah, but, you've only been seeing him three weeks. You haven't even seen him, it's all been on the phone."

"Mom said that you and she got serious because of all your phone calls and emails when you first got together."

"We'd known each other--," he began, but realized he was helping her case. "I mean," he started, but couldn't find words. He turned to Rory, "Tell her what I want to tell her."

"Ella," Rory said gently, "We just want to make sure you go wherever is best for you. And trust me, I based my college off of what my grandparents wanted and where I thought my boyfriend was at the time, but he ran off like a month after I made my decision. Now, I was lucky, it was the best place for me, but trust me—you should do what you feel is best."

"Who was the guy?"

"Jess."

"Uncle Jess?"

"Yes," Rory said sheepishly, and leaned back against Tristan.

"Uncle Jess ran out on you?"

"Ella, we're straying from the point, here," Tristan reminded her. "Now, do you understand what we're saying?"

"Yeah, I do. And thanks, for wanting the best for me. I'll let you guys know as soon as I decide."

"Good," Rory smiled, and moved to hug her daughter. She moved to her father next, and he bear-hugged her. She giggled and left the room to rejoin the other girls in the living room. The lights were out, except the one coming from under the boys' room. She saw headlights shut off outside, and she moved to the window. She saw Jess' car, and she grabbed her jacket and slipped out the front door.

Jess was surprised to see Ella up and out at this hour. He smiled and stopped on the porch steps.

"Hey, sneaking off for a hot date?"

"Nah, just saw you coming."

"Ah."

"How was your date?"

"You knew about that, huh?"

"Jules told me."

"Right. It was okay."

"Not a keeper?"

"Not right now, anyway."

"I don't get it."

"Me either. So, you should get to bed."

"Can I ask you a question?"

"Shoot."

"Were you really the reason Mom chose Yale?"

"What? I doubt it," he shook his head.

"She said she chose it 'cause you were here, and then you took off on her."

"Oh. Well," he started.

"Why did you leave her, I mean, if she thought you were worth staying around for, why didn't you think so, too?"

"Well," he shifted uncomfortably, leaning against the porch rail.

"I mean, what happened?"

"Ella, come here," he said, motioning for her to sit down. He stood in front of her, and crossed his arms over his chest. "What is this about?"

"I just wondered, why did you leave back then?"

"I didn't do so great in high school, I'd sort of let Rory and Luke down, so I kind of went off to find myself."

"To find yourself?"

"To go out into the world, and see what I wanted to do with my life."

"And you found it?"

"After I came back. Turns out it was in New York."

"Oh."

"What's up, kid?"

"I'm trying to decide where to go to school, and Mom and Dad are pressing me not to include Billy in my decision."

"Well, they kind of do have a point," he started. "If you were my kid, I'd tell you the same thing."

"But what are you going to tell me as my cool godfather?"

He smiled. This girl knew how to work people. "As someone who cares about you, I'd say to trust what you're feeling. I'm sure it'll all work out in the end."

"Thanks, Jess," she said, hugging him. "It's cold out."

"Yeah, it is, let's get in."

She opened the door, and went to snuggle down into her sleeping bag. Jess kissed the top of Jules' head, and moved down the hall to say goodnight to Ambrose. After he checked in on both of them, he got back into his car; off to the Dragonfly and that cold shower that was awaiting him.