The annual Stars Hollow Picnic Basket Auction runs into romantic complications when Jess (Milo Ventimiglia) outbids Dean (Jared Padalecki) to win a picnic lunch date with Rory (Alexis Bledel), leading to a fight between Rory and Dean and an even bigger fight between Rory and Lorelai (Lauren Graham) over whether Rory should be hanging out with Jess.
The annual Stars Hollow charity picnic basket lunch auction sparks controversies among couples throughout town. Jess outbids Dean for Rory's basket, causing Dean and Rory to quarrel when Rory abides by tradition and shares the lunch with Jess. Jackson refuses to bid on Sookie's basket after she leads him to believe that she doesn't want to move in together. Luke comes to Lorelai's rescue, bids on her basket, and feeds them both at the diner after Miss Patty sets Lorelai up with a trio of unsuitable bidders
Henry tires of the end runs around Mrs. Kim, and calls it quits with Lane. Rory and Jess hit it off at lunch and Jess leaves with a secret souvenir -- the bracelet that Dean gave Rory, which he picks it up and holds on to after Rory drops it. Sookie and Jackson work things out so well that he proposes and she accepts. Lorelai and Rory quarrel when Rory finds out that her mother lent a sympathetic ear to Dean's concerns about Jess. After Emily agrees with her daughter's distrust of Jess, Lorelai realizes that they're both wrong, and apologizes to her daughter.
- Henry breaks up with Lane.
- Sookie and Jackson get engaged.
- Dean is further enraged by Rory's obvious interest in Jess.
- Mrs. Kim tells Lane that she has her rules about Lane dating so that Lane doesn't get hurt because she's just a young girl.
- Aris Alvarado does not portray the Caesar who is left in charge of the diner while Luke bids on Lorelai's basket.
- Seven Brides for Seven Brothers
- The Boy in the Plastic Bubble
- From Here to Eternity
- Sunset Boulevard
- Stalag 17
- Lorelai – So, I've decided I'm saving myself for William Holden
- Lorelai – Ugh, every great relationship has its obstacles. You'd know that if you weren't dating Andy Hardy
- Lorelai – I have to go call Patty and stop the forced mating process. I feel like Ling-Ling the panda bear
- Jess – Well, it's no Lenny Bruce routine but it has its moments
- Jess – Excuse me, Edgar Bergen, I'd like Charlie McCarthy to answer now
- Dean – Sorry, I'd do a silly walk, but I'm not feeling very John Cleese right now
- Lorelai – You do. One with a couch and a deep knowledge of Freud
- Lorelai – I'm totally into Dungeons & Dragons
- Jess – Ayn Rand is a political nut
- Lorelai – I'm not taking sides. I'm Swiss, babe
- Lorelai – He seems cool because he’s got this dangerous vibe and this problem with authority and he’s seen a lot of Sylvester Stallone movies