Summer Prologue...
Things hadn't gone as Jess had planned. He'd come for his mother who'd gotten mixed up in a ridiculous plot of vegetable proportions, fully expecting to leave town the moment they'd gotten the whole silly, leafy-green mess sorted out.
It was Rory's town after all—and Luke's, Lorelai's, Liz and TJ's, and Taylor's. It certainly wasn't Jess's town and he'd tended to avoid it when he'd had forewarning that Rory would be there. Although the few times they'd shown up in the same place at the same time had always been pleasant enough, there had remained a certain amount of discomfort there for Jess. The place was filled with too many memories of Rory and too many people could read the signs of it upon his face.
But, as it turned out, his sister Doula was pretty cool for a ten-year-old. One afternoon not long ago, she'd decided it was time to show Jess her "most favourite spot in all of Stars Hollow." Without ever knowing the irony, she'd practically dragged him to the idyllic setting of Larson's Pond. There they'd collected stones, the smoothest ones they could find, and Jess had spent the afternoon teaching her the fine art of skipping them across the water's glossy surface until she'd (almost) mastered it. The girl had the wildest imagination, like most children of ten, Jess assumed. The two would often swap stories, the tallest of tales they each could muster, which usually resulted in Doula deciding to write the best ones down, just like her big brother did.
In recent years Jess had also learned that, when he offered Liz and TJ his company more freely, his mother became less clingy and more bearable. In giving of himself, she didn't (have to) try quite so hard and so didn't smother him with unnecessary doting. Without the rampant smothering, Jess was able to see his mother more objectively, often as though for the first time. TJ was still an acquired taste that Jess hadn't quite acquired but it turned out Liz had more in common with Jess than he'd ever realized before.
And now this summer, four years after their last crossing of paths, Jess had delved in deeper with Rory than his guard had previously allowed. She'd pulled a bottle of Scotch and a handy second glass out of the drawer of her new desk at the Stars Hollow Gazette and, though their conversation had still been woefully short and maybe a little distant, they'd had their longest talk in years.
It was good. It relaxed him. It was the final piece of the puzzle falling into place, reminding him that things would be alright. The past could be put behind them, tucked deeply into their hearts next to countless memories, fond or otherwise, of all the people who had come and gone in their separate lives. They could coexist, even in this small, nutty space that she called her hometown, without having to tip-toe or share painfully superficial conversation. He didn't have to avoid visits that coincided with hers. They could just be.
Knowing that, and coupled with his brand new sense of familial affinity, Jess could finally lay claim to Stars Hollow as his own quirky hometown. It was a comfortable, warm feeling, a feeling of belonging, and once he'd felt it, that was when he'd decided to stay for a while.
He'd long been released from the specter of what could have—but would never—be. But it was only this summer, as he'd shot the shit with Rory over a couple of glasses of Scotch, that he'd finally become comfortable with what was: a fledgling friendship and nothing more.
Rory had not been in a good headspace that day. Once again Jess had been surprised to find himself on steadier footing than the darling of academia. It was stunning considering her trajectory when he'd known her all those years ago—how her path, at one time so steady and true, had taken such a bizarre, meandering turn.
So starved had she been for any sense of direction, she'd taken almost immediately to his suggestion that she write a book. (It was the best and only advice he could offer her. After all, his own process had worked wonders for him.)
He'd left her at that, wishing her the best and hoping her trajectory would once again aim for the stars, content that their paths would diverge as time would see fit.
After a week or two he'd briefly returned home to Philadelphia to tend to his life—any adult would tell you that that's what you sometimes had to do.
But before long, the trees had shuffled their green and Jess had returned to Stars Hollow to witness the annual spectacle of red and gold with new, unjaded eyes. And once again he'd stayed, longer than he'd planned, finding calm and inspiration in all the corners of his world, and gaining perspective on his happy life, both at home in Philadelphia and in his new-found hometown of Stars Hollow.