A/N: So, we seem to be of the opinion that Rory got what she deserved last chapter but that Jess will probably regret it (whatever 'it' may be!) when the morning comes. Well, before we see what happens next with them, let's check in with Lorelai... ;)

(For disclaimer, etc. - see chapter 1)

Chapter 28

Lorelai couldn't believe this was happening.

When Lane came around to see Rory, only to find her BFF was out moping for Jess some more, Lorelai was more than happy to fill in as a listening ear. It was actually not so awkward being asked about sex by somebody else's kid, after all much of the time, Lane felt like she belonged with the Gilmore girls much more than with her own mother. It seemed she was having issues of the mom kind even now, finding that, as much as she would like to get closer with Zach and had even been considering the possibility of sex, she absolutely couldn't bring herself to go there - unless he married her first.

Lorelai and Lane had a pretty frank discussion about the whole 'being ready' thing, plus a recap of the most important birds and bees areas - everything from condoms and birth control pills to what to expect when the time comes. Lane had left much happier than she showed up and Lorelai was glad. Unfortunately, a shock had hit her less than five minutes later.

It seemed that Lane had not quite been able to tell Zach that their getting really close was being prevented by Mama Kim's voice in her head. On this occasion at least, she had blamed the time of the month. Thinking about that, Lorelai suddenly frowned, grabbing her datebook from her purse and flipping the pages. She had to flip several before she found what she was looking for, and then she said a couple of curse words that very rarely left her lips.

The trip to the drugstore was made in double-quick time before she thought better of her purchase. Sure, there were privacy rules when it came to doctors, and even pharmacists ought to be discreet, but Lorelai knew just exactly what Stars Hollow was like. If she went in and bought a pregnancy test, the whole town was going to be speculating by lunch time. No, better to go elsewhere to make her purchase. She turned around to head back the way she came and found the diner in her line of sight.

"Yeah, that conversation should probably come first," Lorelai muttered to herself, taking a deep breath and pushing on into Luke's.

Luke himself looked pretty busy when she got there, which was weird considering it was too late for breakfast and too early for lunch. Still, Lorelai sat herself down at a table and waited impatiently for her fiancé to have the time to talk. Even then she was going to have to convince him to go somewhere private for this particular news. Lorelai was thinking all of this when suddenly the diner door popped open with the usual jingling of bells and in walked the last person she expected to see.

"Hi," he said to her, or possibly to Luke her over shoulder, Lorelai couldn't be sure.

"Jess? What are you...?" said Luke, getting no further before his nephew disappeared behind the curtain. "What is he doing here?" he asked Lorelai instead.

"I don't know." She shook her head. "He looked kinda... green."

"I really can't..." said Luke, plates in both hands and more customers arriving at that same moment.

"I'll go," Lorelai offered, knowing somebody should. "It's fine," she promised Luke, dropping a quick kiss on his cheek before rushing towards the stairs.

Honestly, she was almost relieved not to have to have the pregnancy conversation right now. Not that she relished the idea of making nice with Rory's boyfriend or ex-boyfriend or whatever Jess was right now. Maybe the pregnancy conversation would've been easier, even if the whole diner was listening.

Shaking her head, Lorelai knocked on the apartment door, then covered her eyes with one hand and used the other to open the door a little.

"Jess?"

"Lorelai?" he replied, voice loud enough that he had to be right in front of her.

She peeked between her fingers and then sighed, letting her hand drop.

"I didn't know if you were changing clothes."

"I'm not," said Jess, gesturing to his fully-clothed state.

"Cool." Lorelai nodded once, closing the door behind her. "There are certain views a woman doesn't need when it comes to her daughter's boyfriend."

"Huh."

Lorelai couldn't be sure if that response was because he just liked it (which he definitely seemed to) or because Jess didn't consider himself Rory's boyfriend anymore. Right now, she wasn't of a mind to ask. She watched Jess get himself a bottle of water from the fridge, and shook her head, 'no, thanks' when he offered her one.

"So, how're you doing Jess?" she asked then.

"Fine," he told her warily, sitting down on the nearest chair.

"Really?" she checked, joining him at the table. "You look a little less than fine. Good time in Florida? Drink the place dry already?" she asked with a smirk.

"Maybe."

"You throw up?"

"Over about a mile of beach."

"Pretty." Lorelai grimaced. "Paris too?"

"Oh, yeah," Jess confirmed seriously, taking careful sips of his water.

"Well, you two must've looked real attractive."

"Probably. You know, she ran to Florida because her boyfriend told her he loved her, while I ran to Florida because..."

Lorelai waited for the rest of Jess' sentence but it never came. In the end, she figured she may as well try to fill it in for him.

"Because?" she echoed. "You're not sure if Rory loves you? Oh, Jess, she does. She really, really does," she insisted, even as Jess physically turned away from her. "I swear I didn't come up here to plead her case, but since you brought it up, Rory feels just awful about what happened."

"I know that she does," he replied, passing his water bottle from hand to hand, "but it still happened."

"It did," Lorelai agreed, "and I'm not saying that's okay. Rory is my daughter and I love her to death, but I'm not going to defend what she did, Jess, because it was not cool," she said definitely. "That said, everybody makes mistakes, right?"

Their eyes met for a second and then Jess looked away again. He wondered if Lorelai knew. She couldn't, not really. She might suspect the truth but she couldn't really know. Not even Rory knew. Jess wished he didn't know either but as much as the memory was hazy, it was still there. Madeline's lips on his, her hands in his hair. Jess took another long drink of water and then sighed.

"Is Rory at the house?"

"Far as I know." Lorelai nodded.

Jess nodded too, got up from his seat and went over to the closet.

Lorelai wasn't sure if she was supposed to say anything else or not. She wanted Rory and Jess to patch things up if they possibly could, and at least she didn't seem to have made matters worse with her little intervention. That was something. She sat up straighter in her seat when Jess looked back at her, eagerly awaiting the next opportunity to help put the young lovers back on track.

"Er, now I need to change clothes," he told her awkwardly.

"Oh, right," said Lorelai, shaking her head and standing up fast. "Sorry!" she added, practically running for the door.

She headed back downstairs only to find Luke still rushing between the kitchen and all the many tables full of customers. Business was booming, which couldn't be a bad thing, but it kind of scuppered any chance she hoped to have of telling Luke her potential news, both about herself and about Rory and Jess.

"Everything okay?" he asked as he passed by her, empty dishes in hand.

"I think it could be," said Lorelai, unintentionally cryptic as she thought it over. "Um, I'll come back when you're not so busy, or I'll see you later at home?"

"Okay." Luke nodded.

He might've said more after that if he'd gotten the chance, but Lorelai was already gone.


Rory didn't know what to do.

It had been bad enough living with the guilt of cheating on Jess and having him and Paris pretty much cut her out of their lives for the last week or so. Now it was just worse. Yesterday, finally plucking up the courage to try to call Jess or even Paris in Florida had led to her finding a voice mail from Louise Grant of all people, calling from Jess' cell, while the man himself was apparently getting even on his girlfriend with Madeline Lynn. The whole situation made Rory feel so sick.

How could she really complain? As far as Jess was concerned they were probably broken up now, so it didn't really matter what he did. Even if they were only on some kind of Ross-and-Rachel style break, how could Rory be mad at him for kissing another girl when she had started it by kissing another guy? Unless he had gone further than that with Madeline. Rory felt nauseous at the very idea and felt new tears fall from her eyes. Sniffing hard, she dragged the back of her hand across her face and fought for composure, especially when she felt a shadow fall over her. She had company.

"Rory? What's wrong?"

She looked up in surprise to find maybe the last person she expected to see standing over her.

"Dean. What are...? Um, I was just..."

"Crying on the bridge," he filled in for her, sinking down by her side. "Did you fight with Lorelai?"

"No, nothing like that," she explained, swallowing hard. "I, er... I did a stupid thing, and you of all people are going to think I'm horrible."

"Somehow, I doubt that," he told her, smiling kindly. "Come on, what's this horrible thing you think you did?"

"I cheated on Jess."

Rory wasn't sure what reaction she expected from Dean on that one. They had found a way to be friends in a strange way since their break up. She moved on with Jess and Dean actually went ahead and married Lindsay, so it was patently clear to both Rory and her ex that they were the permanent kind of over, with no hard feelings left to bear. They said 'hi' to each other if they met in the street or a store, ran through the usual pleasantries, but they really hadn't had any kind of real deep conversation in more than a year.

"You cheated on Jess," Dean echoed. "Wow."

"Yeah, I know. Kind of a habit with me, isn't it?" said Rory sadly, looking down at her own hands in her lap. "I can't believe I was so stupid. I really never meant for it to happen, it just did. I mean, Logan kissing me, I know I should've stopped it but I didn't, it happened so fast. I think Jess could've gotten over that but then... then I was dumb enough to go ahead and kiss Logan in what had to be a moment of weakness or madness or... something. All I know is I really, really wish it had never happened!"

By the end of her rambling speech, she was crying again. Dean put an arm around her and rubbed her back in a friendly gesture of comfort.

"Well, so much for thinking you two wouldn't last," he said, shaking his head. "I never wanted to believe it was real with you guys but you really do love him."

"How can you say that?" asked Rory, swinging her head around to look at him so fast she nearly gave herself whiplash. "If I loved Jess as much as I should, I would never have done what I did."

"Okay, that's one theory," Dean considered, "but look at it this way, when we were together, you kissed Jess, and then not long after that, we broke up so that you could be with Jess," he recapped, managing not to wince at all as he said it. "Now you say you kissed this Logan guy, but you're not breaking up with Jess to be with him. You're sitting on the bridge crying your eyes out because all you want is to have Jess forgive you for your mistake. That has to prove something, right?"

Rory sniffled and nodded her head.

"I guess so," she agreed. "I mean, I do love Jess. I love him so much and I... I just wish it was enough. I'm not sure he loves me anymore, not after what I did, and then he and Paris went to Florida for spring break and I think he... well, he met up with these girls and..."

She was crying on Dean's shoulder again and he let her. It hurt him to see her in so much pain but for once it wasn't his place to jump in and play hero. At last, he had moved beyond believing he was the Prince Charming in Rory Gilmore's princess-like life. It might've been nice, but their time had passed. Like he just told her, she was proving how much she loved Jess with the way she was feeling so guilty and sad right now.

"People make mistakes," he told her, hugging her close, "but when you love someone for real, it never goes away, no matter what happens."

Rory pulled away to look at him then and saw an old familiar spark in his eyes. Dean was her past, she was sure on that, but it was nice to be friends again, to be able to remember what they once meant to each other and have that be okay.

"I'm sorry, Rory, but I really have to go," he said then, catching sight of his watch. "Lindsay's expecting me home."

"Go," she told him, smiling bravely. "Thank you, Dean. You helped... a lot."

He smiled and nodded as he got up to leave. Rory watched him walk away and she sighed. She really never expected to be finding comfort and good advice from her ex like that, but he genuinely had made her feel better about things. He made an excellent point about her true feelings. When she started things with Jess, she didn't feel as guilty as she should because she already knew she and Dean could never work out. This situation was so different. She didn't want Logan, not like that. He was a nice guy and as a friend he was just fine, but it was Jess who Rory loved. She didn't believe she could ever love anyone else as much. If that was true for him too, and she was pretty sure it was, they could work through anything if they really wanted to.

Getting up from the bridge, she dusted off the back of her pants and turned to walk home. She stopped after just one step when she realised she was not alone.

"Hi," she said to Jess, wiping at her tear stained cheeks with both hands.

"Hi," he replied in kind, hands shoved deep in his pockets as he wandered towards her. "I think we need to talk."

To Be Continued...