145. We've Got Us a Pippi Virgin (Season 5, episode 5)
This episode is so bad on so many levels. Dean and Rory's second attempt at dating is just sad and pathetic. He no longer has any chemistry with either Rory or Lorelai, partly because they both know that this relationship was doomed to fail simply because of how it started, partly because they've outgrown each other, and partly because Dean has apparently outgrown his personality and is now a lifeless sack of nothingness that sucks the fun out of every scene he's in. The scenes with their double date with Luke and Lorelai are unbearable to watch. We know that Luke got a little out of hand at times, but honestly, can you blame him? He's the only one who is actually willing to say what everyone is thinking, which is that this relationship is a mess and should end immediately. And Lorelai and Rory make the world's worst matchmakers.
High points: Poor Jackson. He really is trying to help the town, but not everyone enjoys micromanaging everyone else's lives quite as much as Taylor Doose does. Jackson isn't really cut out for the job, but it is sort of fun to watch him squirm. And Emily's panic room, while pointless and a strange waste of money, is hilarious.
Low points: Dean's emotionless face, that awful Pippi Longstocking song
Best quote: "How dare he have a vest like that!"- Emily
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The Definitive Ranking of All 153 episodes of Gilmore Girls
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