The show opens the day before the Stars Hollow Bid-on-a-Basket Fundraiser, with signs telling the viewer that bidders can win themselves a delicious home-cooked picnic lunch, that it’s held on Sunday at midday, and that all proceeds go to the Stars Hollow Retirement Home (the signs are sponsored by Doose’s Market). Across the street at the market, baskets are on sale, and more signs tell us that it’s also known as the Bid-on-a-Basket Festival. We can see a woman leaving with her new basket.
Inside the market, Lorelai and Rory are shopping for their own baskets, but of course they don’t intend to cook a delicious home-cooked picnic lunch (or even make Sookie do it for them, like they did for the bake sale). They’re just going to put old leftovers in their baskets – as we now know they keep leftovers for a long time, it’s sounding like a Salmonella Festival for anyone bidding on their baskets!
These type of fundraisers are called “box socials” and were common in the 19th century and 1900s, with women cooking the food and packing it into a box or basket, and men bidding for them. Although it was meant to be a “blind” auction, married and attached women would let their husband or sweetheart know which basket was theirs, so they could bid on it – bidding on a woman’s basket was a way to let her know you were interested in more than her home cooking.
Box socials are also low-key dating auctions, with the winning bidder not only getting the basket, but the chance to share the picnic lunch with the lady who provided it. A lunch basket auction of this type features in the 2001 YA novel Flipped by Wendelin Van Draanen (in this case, it is a high school boy who provides the basket, and girls bid on the chance to have lunch with him). This seems like a bit of a coincidence, or perhaps merely zeitgeist.
Although Flipped is set in the 1990s, when it was made into a film in 2010, they set it in the 1960s, as if that scene was deemed too old-fashioned to be believable. They must have agreed with Lorelai, who complained that the concept was “backwards”. In fact there has been a mild resurgence in box socials since the 1990s.
The show never makes it explicit, but according to the timeline, the Bid-on-Basket Fundraiser seems to be held in mid-February, and it would make sense if it was the Sunday after Valentine’s Day. That’s a clear connection with love and romance, although it isn’t practical at all to have a picnic in winter! In real life it would be freezing.
The Annotated Gilmore Girls 
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