Jackson proposes to Sookie during the annual Bid-A-Basket festival on Gilmore Girls.

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Gilmore Girls
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Gilmore Girls Season 2 Episode 13: "A-Tisket, A-Tasket"
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Gilmore Girls Season 2 Episode 13 Quotes

While having their picnic at the lake
Rory: Wow a place in Stars Hollows that you actually like!
Jess: Yeah I have some good memories of this place. See over there, that's where Luke pushed me in!

Lorelai: Every picture you ever see of people at a picnic they are eating on the ground.
Luke: And every time I see a picture of people having a picnic on the ground I think "What the hell are you people doing eating on the ground? Get up...get some beach chairs you cheap skates!"