Thanks for the feedback! This is a chapter from Jess's POV in S7.

It's a big day for her. Jess knew it was soon, it had to be, but he didn't know it was this soon until he got the email from Rory. I'm graduating next week. Just thrown in there surrounded by all the typical, every day news. Classic Rory. Jess wrote back: Damn Gilmore, talk about burying the lede. What day? I'll be there. Pausing, he stopped and sat back in his chair. Does she even want him there? Jess deletes the last sentence and writes the usual congratulatory crap. I'm happy for you. He means it though, he is happy. He's proud of her.

It took a while for Jess to think about Rory without feeling some combination of anger, sadness and general pissed off-ness. A winning formula. Same kind of formula he applied to his mood when he moved to Stars Hollow, and Rory was the only one who could add something resembling happiness to it. Kind of sickly ironic that she turned it the other way. Poetic, or whatever. As he said to Rory, he'd have to get Matthew's poet to explain that to him. Jess never cared much about poetry.

He was so mad at her that night. He was so mad, but more than that he was sad, only sad is too small a word. It was a physical ache. The only time Jess remembers feeling something like it was years ago, when Rory kissed him at the wedding and ran off to Washington after making him promise 'not to say a word' and he waited. Jess didn't receive any kind of word from her, not an email, letter or smoke signal, and when she did come back she was still with Dean. There goes the poetry again, Rory Gilmore breaking his heart. But they were kids back then. She broke his heart again, when she said she had to let him go, and a year later, when she wouldn't go with him, but at least with those times Jess knows he hurt her, was asking too much. She couldn't rely on him back then. It's different now. He's got himself together, figured some life out. He doesn't deserve this. He told her that, and Rory said she knew. And she walked out the door, taking his heart with her.

Jess was mad at himself at first, after she left. Why the hell did he think she was here to get back together with him? Rory never actually said she'd broken up with that guy. He'd been dumb, but later, Jess thought, he hadn't been totally blind. He asked if everything was fixed and she said yes and they kissed. Rory kissed him, and even though moments later she was freaking out, she was kissing him back. Jess felt blindsided when she stopped, started burbling, and when he reminded Rory that she'd said 'everything was fixed' she'd said everything but him. Which implies to Jess that she wanted it to be fixed. She didn't want to be in love with him. Jess was mad about that too, still is, actually. He was so proud of Rory, getting it together and going back to school and yet here she was, supposedly in love with the guy who cheated on her. Jess knew that guy was a jerk from the second he saw him. Jess and Rory made fun of guys like that! She knew guys like that at that fancy school of hers, guys who either ignored her or teased her, but back then Rory didn't care. She was smarter than they were, didn't need them, didn't need anyone and Jess loved her for it. She went Yale and something changed. Something had to have got screwed up because Rory was trying to keep this guy's attention, stay in love with this jerk who cheated on her. What the hell! This wasn't her, this dropping out of school, living with her grandmother and dating a guy her grandparents would approve of. Rory looked better than when Jess saw her last but she was still totally hung up on this guy and he can't figure it out.

From the little Luke says and Rory's emails, Jess assumes she's still dating him (as for love, he can't say). Jess didn't hear from Rory for a while and like hell was he going to talk to her. He'd used that girl Shane the last time Rory ran out on him (and she used him too, so it wasn't exactly sad when he ended it) but Jess is a little more mature than that now. He's not going to use someone to piss Rory off (not that either of them are still in Stars Hollow, thank God) and anyway, what's the point? She's broken his heart but she didn't use him. Call it naive or whatever, but Jess doesn't believe that. He managed to pick up in her burbling something about wanting to cheat on that guy but couldn't. Jess told her she could tell the guy they 'did something' and if Rory did or not, he doesn't much care. What they did do is real. Jess knows Rory. When she kissed him back she meant it. She's going through some shit but Jess knows that kiss was real. Not that he's telling people that. He gave a watered down version of events to Matt and Chris and they'd pushed a beer in his hands, clapped his back and said something along the lines of us all acting dumb when we see our high school girlfriends. Jess nodded, stayed silent, and for some reason Logan's crack at him popped up in his head. You two highschool sweethearts? Rock around the clock, two straws in the milkshake? Jess had laughed at that. As if that was all he and Rory were. That guy wishes it was all Jess and Rory are to each other. He's still dating Rory, so maybe Jess isn't one to talk, but he's positive that he knows Rory better than this guy. Jess knows this. He knows her. What kills him is that Rory almost seemed afraid of breaking up with him, like she couldn't be enough. The girl who skipped school and went to New York to see him doesn't think she can be enough. Jess doesn't know what the hell happened.

Either way, Jess also knows that he can't sit around hoping Rory will wake up and dump that guy. He's not going to wait for her. He knew that even when they were kids and she went off to Washington. Knew that when she wouldn't go with him and Jess had to get his life together. Some months after that night at Truncheon Matt introduced him to Sarah, another publisher, and they dated. It was nice too, nothing earth-shattering, but nothing heart breaking either. Jess knew that when Sarah got a job offer in California and ended things. Jess was a little sad but also a little relieved, and got the sense that Sarah felt the same way too. They hugged goodbye as friends. Jess had a few dates here and there after that, and more than one date with a poet called Alyssa. Jess should've known dating a poet was a bad idea. She was like him, probably too like him if he's being honest, both them of shutting down if they were pissed off and preferring to have sex rather than talk. One day Jess found her crying over some card and after sitting with her, asking if she was okay, Alyssa stopped crying to tell him the card was from her ex-boyfriend and he wished her a happy birthday and was going to be in town soon. She had never gotten over him. Jess could tell that, even before she said it through a new set of tears, and through his sudden guilt at realising he hadn't known it was her birthday so soon. He'd squeezed her hand, said it was okay, and maybe for the best if they quit whatever it was they were doing. Alyssa didn't fight him on it and, as Jess went home, he remembered Rory's birthday wasn't so far away. He thought about sending her an email but was still too mad at her. Jess felt frustrated at that - he'd gone out with two women since, what the hell - but he still felt that crazy rush of anger and sadness. Less so, but it was still there. Still too much for him to write to her.

In the end, Rory wrote to him first. Jess had actually seen her that day. He'd been on a trip to Stars Hollow, seeing Liz and his new little sister, and Jess had caught sight of Rory walking across the town square with Lane. Jess had lifted a hand before he could catch himself and Rory stopped, gave a kind of wave back and a half-smile before quickly walking away. Jess didn't go after her but he'd got an email and stared at it, heart thumping, before finally opening the damn thing.

Hey, it's Rory. I hope this isn't too weird. You can delete this if you want and maybe you already have so you're not reading it, so I'm basically talk to air…

Jess smiled in spite of herself. Typical Rory ramble. She'd cautiously written a few more lines, carefully leaving out a mention of that night or that guy, except for, at the very end, saying, I don't blame you if you don't want to write back. But I wanted to say hi. Oh, and congratulations on being a big brother. Rory.

It ended a little abruptly but Jess didn't mind. He wrote back saying it was kind of weird being a brother after basically being an only child his whole life, but kind of cool as well. Rory replied, saying she got it, that it felt strange being a big sister when Gigi was born, and she still doesn't feel like a sister to anyone as she hardly knows Gigi and it was only her for so long. Just me and Mom, not that it was a bad thing. I'm seeing Mom tomorrow, actually.

Jess was glad she and Lorelai made up. He wonders what Lorelai thinks of this guy, of Logan, and if her opinion of him is any better than it was of Jess. Not that that's a particularly high bar. It was all over ever since Jess swiped that beer and accused her of sleeping with his uncle, definitely over after Jess took Rory's bracelet. That lady can hold a grudge. Not that Jess was desperate to make friends with her either. Luke is dating her now, got back together with her after he messed it up, she messed it up, whichever, but Jess hasn't seen Lorelai. He suspects the grudge is still there. It was crazy that she and Rory didn't speak for so long. Jess may not be Lorelai's biggest fan but that had to have sucked for her and he knew it sucked for Rory. She didn't tell him that but Jess could see it. He didn't say that in his email though. He wrote back something boring like it sounding fun and so their emails went, updating each other on their lives but both being careful to avoid what happened between them. Jess thinks an email is too cold to bring all that up and anyway, he guesses Rory doesn't want to go there. He's okay just being friends with her, if that's what she wants. Jess doesn't know if it's worth risking anything more, even if there's a possibility. They exchange new cellphone numbers but never call.

And now she's graduating. Seems like yesterday she was babbling about going to Yale so determined, so excited to start this new path to a new world. Jess didn't get it but he loved it. He loved her. He'd smile and sit back, letting her talk, and think about that 22.8 miles which he'd looked up on the school computer. Jess had got a map of Connecticut and already planned all his visits to Yale, hanging out with her and having all the time they wanted without adults interrupting. They would have all the time to do anything and Jess knew that even though it was going to be hell, her going away for a whole summer and then being away at college, it was going to be worth it. She would come back and he would go to her. Then of course, he blew it all up, didn't graduate and broke her heart. He left her and Rory never forgave him. Jess knows that. He knew, back then, she wouldn't want to talk to him, but he had to talk to her, hear her voice, but whenever she answered the phone his courage was gone. So finally she talked on her graduation day, saying goodbye. She was starting out on her path and Jess had to find his own. He wonders what her path is now.

The week passes quickly. Jess gets an email back, telling him the day of graduation, but there's no invitation. Jess didn't expect one but it stings a little anyway. He reads the rest and starts to reply but everything sounds bland. Jess can't send an email of hallmark crap. He wants to see her. Jess wants to be there so badly he even starts looking for a clean shirt on the morning of her graduation, mentally calculating how long it will take to drive there, before stopping. What the hell is he doing? Rory didn't say she wanted him there. Jess doesn't think she'd be mad but it's her day, and she might not be okay with him just showing up. He could go anyway and stand at the back, out of sight, but that feels pathetic and a little creepy. Jess sends an email simply saying Congratulations and puts the clothes away. He can't go on with his day, though. When he knows the ceremony has finished Jess dials her number, holds his breath and takes a second to release it after Rory says, "Jess?"

"Congratulations, graduate."

"Thanks. One more word than your email."

"I'm not one for speeches."

"Feeling a little succinct today?"

"Something like that." Jess pauses, takes a breath and says, "I'm really happy for you, Rory."

"Thanks."

"I'm proud of you."

"Thanks," Rory says again. She sounds more serious now and still does as she repeats, "Thanks, Jess."

"I mean it. You graduated."

"Thanks," Rory says and then laughs. "I need a new word."

Jess laughs as well. "It works. Congratulations."

"Thanks," Rory says teasingly and they both laugh. Jess wishes he could actually see her as he says, "Is this okay, me calling like this?"

"Of course it's okay," Rory says, sounding surprised. "Why wouldn't it be?"

"Come on, Rory. You know."

There's a pause and Jess closes his eyes.

"Sorry," he starts to say and Rory interrupts.

"You're not the one who needs to be sorry. I'm the one who screwed up."

"I know, but it's your graduation." They're both silent and Jess awkwardly jokes, "This worse than me calling at your last graduation?"

Rory laughs down the line, making Jess smile. "I hadn't even dropped out back then. Years to look forward to."

"That's right, I'm the one who dropped out. I'm glad you went back."

"Yeah?"

"Rory, you belonged there, at school. You love learning."

"You loved learning too," Rory challenges and Jess imagines her nod as he replies, "Yeah, but it was different for me. I had to learn my own way - I never wanted to go to college."

"I know. You always had your own plan."

"I don't know about that," Jess chuckles. "But I had my own ideas and they definitely didn't include Stars Hollow."

They both laugh a little and Jess says, "Hey, this day is about you graduating. What's your next big step?"

"Oh, I don't know. I've applied for some jobs."

"You'll have to beat down the offers."

Rory laughs at that. "I already got rejected for an internship."

"That sucks," Jess says, feeling a little clumsy. "Their loss."

"So everyone says."

"They have a point."

Rory makes a non-committal sound and Jess waits, puzzled, until she says, "I need one of those jobs. That's what I said to Logan."

"Right," Jess says, his mood souring a little. He probably bought her a car to make up for it.

"He broke up with me just now," Rory says. "He proposed and I said no."

She sounds as if she were simply telling Jess her weekend plans but her words shock Jess so much he stands up, his heart running something close to a marathon in his chest.

"All in a day's work," he says weakly and Rory laughs, sounding a little sad.

"Something like that. He wanted me to go to California with him and I said no. I want to figure out my life a little first."

"Are you okay?" Jess asks stupidly and then closes his eyes. "Dumb question."

"No, it's okay. I actually am okay, I think."

"Good," Jess says and then closes his eyes. He kind of does think it's good she broke up with the guy but it seems kind of callous to point it out. "I mean, good, you're good. I…"

"I know," Rory says. "Thanks."

Neither of them point out the repeated use of the word. Jess opens and closes his mouth, unsure what to say, and hears a woman call Rory's name over the phone.

"That's Mom," Rory says. "I should go."

"Okay," Jess says. "Congratulations, Rory."

"Thanks, Jess."

He can easily end the call now but he doesn't, and neither does Rory. They hang on, Jess trying to find his words, just like on that first graduation all those years ago, until he hears Lorelai call again.

"Sounds like you have to go," Jess says eventually and Rory says, "Yeah. Thanks for calling."

"Of course. You know you can -" Jess stops himself but Rory asks, "What?"

"Just that it's cool talking to you." He was going to say she can call him but it sounds weird.

"It is," Rory says. She sounds happy. "I'm glad you called."

"I didn't know if you'd want me to."

"You know I do," Rory says, somewhat enigmatically. "Bye, Jess."

"Bye, Rory." And with that, the line is dead, and Jess is sitting here with a bombshell.

She's finally fixed everything. Jess is proud of her, not just for graduating, but for seeing herself the way she should - better than a jerk who cheats on her, smart enough for anything she wants. She's ready for whatever her next step will be, Jess is sure. He's proud of her, but he knows it's more than that. It's good he didn't go to graduation because Jess is sure that when he looked into Rory's eyes, hell, just see her, he'd want to hold her again, kiss her again, and he knows how that ends. Some might say he should walk away from her entirely, lead a separate life and maybe they're right, but Jess wants Rory there. She sees him, somehow, and he sees her. Jess can't explain it. What they have, what they are is too complicated. It is what it is, you, me. That's what he said to her that night and it hasn't changed. Maybe one day something will change, maybe not. Jess doesn't know. All he does know is that Rory graduated today and he wants to give her something. Going downstairs, he wanders around Truncheon, staring at the shelves before a book stands out. It's from a new writer, all about moving to New York, and it's perfect. Jess scribbles some thoughts in it, finds a card and hesitates before simply writing: put some thoughts in the margins for you.

It doesn't say a lot but Jess hopes it says what he needs to. He remembers the girl he tried to impress with that, so many years ago, and smiles at his younger self. He's not trying to impress the woman now but he still wants her to get the message: I see you. They have always held this understanding.