Start: S4E02: The Loralais First Day at Yale
End: S6E22: Partings
I enjoy Gilmore Girls. But, full disclosure, I started watching it when I was recovering from surgery. I started from the beginning and I probably would have stopped if I hadn't been so drugged up because, let's just say it: Loralai and Rory are insufferable. And Luke and Dean are no prizes either. The charm of the show comes from the chemistry between mother and daughter large cast of side characters. I wouldn't want to sit behind Rory and Loralai at the movies, but through the distance of television, I can enjoy their banter. I would return to Star’s Hollow every day for Miss Patty, Sookie St.James, Paris Geller, and queen of my heart Emily Gilmore*.
The fourth season is the perfect jumping on point. Season one starts with Rory beginning classes at Chilton. Season four recreates several of those beats by starting with Rory beginning classes at Yale with the major difference that the chemistry between Lauren Graham and Alexis Bledel has had time to gel and the large cast of characters is fully formed. Bonus: there is still another Dean versus Jess subplot yet to play out, so even if you skip the first three seasons, you can still weigh in on that debate.
But stop before season seven. That season is famously terrible, suffering from the loss of creator Amy Sherman-Paladino. The love lives of the Gilmore girls are still in question at the end of season six, but take my word for it, the resolution is not any more satisfying if you stick it out for the last twenty-two episodes. Most importantly, this season has the best resolution for Lane Kim. By stopping here, you can remember her as a drummer, married to a man she loves in an awesome double ceremony that let her know she had more in common with her mother than she thought. You can pretend that this never happened.
When you’re done, you can go back to season one and watch through the end of season three. Then, I suppose if you’re really Jonesing for more Stars Hollow, you can watch season seven and (if you must) Year in the Life. (But you’re probably better off just watching Bunheads.)
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*I know two of those four characters don’t live in Stars Hollow. Don’t @ me.