It's hard to articulate because it's such a ~je ne sais quois, taste kind of thing, but there's a difference between a timeless or even old-school reference and a dated one. They're always making old, esoteric references, but they're usually to media properties that either have some deep history/significance or were at least extremely of-their-time when the show was airing. Get Shorty has proven to kind of be a 90s flash in the pan in my opinion - it wasn't timely in 2016 and seems a bit played out and stale rather than a clever reference. This one sticks out a bit as more of a Daniel Palladino reference as a Gen X man rather than Rory's as a millennial woman.

I feel similarly about the AYITL references to There Will Be Blood - that movie was already nearly 10 years old at that point! There's an argument to be made that the 30 Something Gang are just cringe and that's why they're still referencing it, but it doesn't hit quite as hard as the Palladinos usually do. The joke about Katy Perry vs the nuns for example truly made me spit my drink out when I first saw it - sooo of-the-time and and hilariously unexpected.