LORELAI: Well, last year Roy Wilkins bought it and I got my sprinklers fixed for half price … And this year my rain gutters are completely clogged, and I thought if I could get the Collins kid to bite, I’d get that taken care of.
We learn that the previous year, in 2001, a man named Roy Wilkins bought Lorelai’s basket at the fundraiser, and she was charming enough to him that he fixed her sprinklers and only charged half price for it. This year, she was hoping that “the Collins kid” might buy her and be inveigled into cleaning her gutters for cheap or free.
“The Collins kid” could be in his early twenties, I don’t suppose Lorelai would picnic with a literal child? Although considering how the town laughed at her for going on one date with someone in his early-to-mid twenties, you’d think she’d be wary of that now.
It sounds as if since becoming a homeowner, Lorelai has been using the Bid-on-a-Basket Fundraiser as a way to get free or cheap home repairs or home maintenance done. Hmm, you know who is really good at handyman stuff? Luke! And now she’s having a picnic with him.