First of all, this thread is everything! It’s extremely gratifying to read all of your opinions, even when I don’t agree with them, because you guys get your point across so well. :)
I apologize beforehand for the rant below:
My UO is that I liked season 4 way better than season 3. Actually, 4 is my favorite season, although 2 is objectively better. I think Season 3 while having some brilliant episodes (“They Shoot Gilmores, Don’t They?”, “A Deep Fried Korean Thanksgiving”, “The Big One”), just dragged out in some parts, not to mention that I disliked the aimlessness of Lorelai’s arc up to “A Tale of Poes and Fire” late in the season - and felt that there were a little too many filler episodes for my taste. And don’t get me wrong, Season 4 has its share of filler episodes as well, but I liked how they were mostly set against the backdrop of Lorelai and Rory adjusting - and floundering - to the big transitions of their life. Lorelai’s Dragonfly arc, in particular, is a big highlight for me - it’s such a fulfilling storyline for her character. And the buildup to Emily and Richard’s separation was incredibly well-written, as was the Rory/Dean stuff (interestingly, I disliked both of these storylines in season 5).
In regards to Jason, I liked him as a character - he was quirky and quick witted, and it was compelling to watch Lorelai hitting it off with a rich guy of her parents’s world. I do think that he brought out a more entitled and carefree side of Lorelai (moreso than, let’s face it, she already is), such as on their first date at the grocery store, when Jason bribed a guy to allow them access to the stockroom, and they both made a mess in there and punched random employees in on the time clock. Not the shining moment of either of them, tbh.
I wished we would have seen him interact with the townies (Babette, Miss Patty, Taylor, Luke) because it’s always intriguing to watch Lorelai’s two worlds clash.
Thematically speaking, I enjoyed the parallels that were drawn between him and Lorelai, and how his character was a sort of foil to hers - both have a similar sense of humor, are stubborn and self-absorbed to a fault and have a tendency to manipulate people into doing what they want then to do, yet whereas Jason has a vindictive streak and acts on a vendetta against his parents, Lorelai feels more protective of hers than she’d ever like to admit, and ultimately chooses them over him, and imo, is overall more kind-hearted, selfless and willing to set aside her wants for the people she truly cares about when push comes to shove.