When he showed up 2 years later for Luke and Lorelai's wedding festivities, he knew she was still with the guy.
Luke had told him so, pretty quickly after asking him to be best man.
"You should know, Rory is maid of honor." He said.
"I figured as much." Jess had laughed, who else?
"Rory's with Logan." Luke had said, hesitantly.
Jess bit his lip, bit back the first thing that came to his mind.
"Dick." He thought.
"OK.." he said, hoping he hadn't hesitated for too long.
"I just wanted you to be prepared." Luke faltered.
"Always prepared, like a boy scout." Jess joked.
"You're no boy scout." Luke snorted, affectionately.
Jess did prepare. Mentally, for weeks and weeks, he prepared, in the back of his head he made sure to keep Rory Gilmore on his "old friends" list. He pushed away anything else.
He carefully sorted through, filed, and sealed any memories that would affect her new life with Dickhea---.. er.. Logan..Logan Logan Huntsorfusion or Huntsenstein or some shit.
Dammit Mariano, he thought, ya gotta be nice. She loves him.
She loves him.
Him.
Not Jess.
And this was a cycle he always found himself in, for those weeks,
Calm, forgiving, practically kind,
then he'd remember the Porsche asshole, the way he slung his arm around Rory's shoulders and smirk at Jess, he should've just pissed on her like a dog to show Jess she belonged to him.
Mark his damn territory.
Jess hated the way she let him.
The day she came to see Jess in Philadelphia and let him kiss her only to tell him she was in love with Logan.
"Despite all the bad he'd done."
Christ, he didn't deserve her.
Of course..Jess knew he didn't deserve her either.
He'd messed up too many times.
She'd never trust him, she couldn't.
He was going to be 25 soon after the wedding.
And he still loved the same girl he loved when he was 17.
Fucking pathetic.
He was sure he'd gotten it together by the time he made his way to Stars Hollow for the first time in years.
He wondered if it would look less Mayberry,. If Luke would be less cranky, If Lorelai talked less or if Rory was different.
He bet she wasn't.
He knew she'd moved back home, gotten back to Yale. Graduated, got a great job tracking the now President.
He practiced deep breathing like a fool focusing on the good in his life, he was a twice-published author.
He had good friends,
Truncheon was opening a branch in New York City soon.
He didn't have to worry about money.
He was a semi-good person.
Just fucking Breathe….
He pulled up to the Dragonfly Inn. Lorelai had graciously offered him a room for the 2 weeks he'd be there getting ready for and participating in the wedding.
The wedding that was finally happening.
Jess shook his head and smiled to himself. Of course he was happy for Luke who had pouted and pined around (for way before Jess was around) over the elder Gilmore girl.
Jess had a flash of himself then, in his forties, hat backwards and snarling at everyone but a bright, bouncy brunette with eyes the color of sea glass.
He sat in the car for a full ten minutes reeling.
Rory didn't understand why she took so long on her hair that morning.
Logan wouldn't be there for another week.
It was calming for her, drying, curling, brushing, messing with her too long bangs (why did she decide to cut them again?)
When all was silken and shiny, flowing down around her shoulders and back. There was nothing else for her to fix.
She had to come to terms,
Jess would be there today.
She had no idea what she would say to him. She had been horrible 2 years ago. She never called or wrote, although she had wanted to.
She loved Logan, and Logan hated Jess, she never let him put Jess down, and sure he had tried, after Jess' second book hit the bestsellers' list, Logan began to mock and she had silenced him for good.
Jess made Logan nervous.
He should. She thought blithely.
Stupid. She reprimanded herself.
She made her choice,
she chose Logan. She turned down his proposal and eventually still got back with him.
Jess was better off without her.
She took a deep breath and looked hard into the mirror.
She could do this.
She thought of dancing with Jess at the wedding.
There was suddenly more to be done with her hair.
Lorelai smiled at Jess gently. A big difference from his last encounters with her years ago.
He smiled back,
Awkwardly hugs her.
"Congrats, bride." He says.
"Thanks, best man." She grins.
They stand weirdly for a minute nodding and looking at each other, waiting.. she finally hands him a key.
He thanks her and makes his way upstairs.
He thinks mildly that she hasn't aged a bit.
Rory wonders why it's Jess' arms she falls into crying instead of her Mom's when she gets back from finding another woman in her bed with Logan.
Jess takes care of her like a baby bird.
He holds onto her and reads to her, he brings her coffee and makes stupid jokes, she never laughs out loud but her eyes dance for a split second before she starts to cry again and he knows he's making some progress.
He never says anything bad about Logan, the entire time he wants to drive there and tear Porsche-dick's head off and kick his perfect teeth out of his pretty face, but he keeps that to himself and just focuses on Rory and making her feel OK again.
She ended up in his bed one night,
He turned her down when she asked him to make love to her.
She cried and tried to leave.
She was too weak to go when he pulled her down and curled up behind her kissing her hair and telling her to wait, wait, wait.
He wants her to be sure.
He wants inside her.
He hates himself for that.