8. Daddy's Girlfriend - Part 1 & 2 (Season 3, Episodes 4 & 5)
Louie effectively makes use of the manic pixie dream girl in season 3, which is a bit odd considering his biggest crush throughout the series, Pamela, is the furthest thing from that archetype. Liz drags Louie into an infatuation spiral as the adorable bookstore clerk, and you can't blame him. After Louie successfully asks her out with all the awkward, clumsy charm you'd expect from him, she takes him on the weirdest date ever to play out on screen.
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