This is based off my post-original series headcanon, not AYITL compliant because let's be real- that is not what happened.
Any shipper deserves to know that this video exists:
https://www.youtube.com/watch?v=_4eycMfGyIQ
For this "chapter" I'll be explaining the general headcanon I have as to where Jess is between 3.21 "Here Comes the Son" and 6.18 "The Real Paul Anka". It's possible that I'll write a prologue, but this is just so that everyone knows where Jess is at immediately after 7.22 "Bon Voyage".
Post 3.21:
Jess lives with Jimmy and Sasha now. He sleeps on this couch:
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and keeps to himself. He only has what is in his bag, so he doesn't take up much room and he doesn't have enough clothing to make the mess that he made at Luke's in season 2.
I imagine he wouldn't want to stick around the house that much, having had to convince Jimmy into letting him stay. He doesn't feel incredibly welcome, really. So, instead he spends his day walking around the area and discovering the places that he would rather spend his free time.
These places include:
1. A remote corner of a beach, one that is more rocky and less hospitable to families on vacation or sunbathers that like to gawk.
2. The boardwalk shops where he can find weird little books and albums to buy along with other odds and ends.
3. A local library, one that has a great collection of classics as well as local books that is part of a larger network of libraries that make it easy to get whatever book you'd like to read... in 3-5 business days.
He also, I would imagine, get a job at a WalMart with the recommendation from his old WalMart positions.
So, there we have it. He wakes up early, gets himself some food, reads until he has to work, works, eats, chooses one of his 3 places, and then comes home once he's sure that everyone else will be asleep, finally able to make his way through the sea of dogs without making them howl. Doesn't make friends, but meets some interesting people.
I imagine that he's a lot like Matilda at this point, reading everything he can get his hands on.
Eventually Sasha, Jimmy's partner, would take notice of the fact that he doesn't interact much with people. Let's say that it's about a month into Jess's not-seen-and-not-heard routine and Sasha finally confronts Jimmy about maybe being Jess's friend. Sure, he shouldn't try and insert himself as Jess's dad, but he should do something!
Cue Sasha trapping Jess into the first family dinner complete with her daughter talking about what she's doing at summer camp and feeding the cats bits of ham underneath the table. There is a totally not rehearsed moment where Sasha cues Jimmy to talk about the few things that he needs done around the food stand. Like, for instance, the fact that the whole shack needs to be repainted. It'd take too long to do on his own and he can't spare the workers to do it because the summer is just so busy and... oh, Jess! You could do it, couldn't you?
Jess borrows some of Jimmy's clothes to paint, making him look the least New York that he has ever looked in his entire life. He gets a tan too, standing on the beach all day long. Jimmy starts getting Jess to do more stuff to help, like fixing drawers and doors and shelves and such. They start to bond. In the meantime, Sasha also gets him to help her around the house so that he can get even more experience being a handyman. She convinces him to take some payment.
