Dean plays softball on Saturday mornings during the spring, and this time last year, Rory would attend his games to support him. But it seems that it has been a long time since Rory bothered coming to a game – which is interesting, because the start of softball season just so happens to be around the time of the Bid-on-a-Basket Festival, and Rory’s “friend date” with Jess.
Instead of going to watch Dean’s game, Rory is shoe shopping with Lane. And afterwards, she has Philosophy homework to do (a new subject for Rory). Dean pleads with her to at least bring her homework to the game, which sounds like a terrible idea, and is. Rory reminds him they’re seeing each other that evening, and that’s all the Dean she feels like seeing that day.
It actually seems more healthy that Rory is making time for friends, and school, and Dean in her life, but both Dean and the viewer can feel that Rory is losing interest in him.