Unpopular opinion: Rory wasn’t wrong to go have lunch with Jess after the bid a basket
He won the basket. When she and Dean agreed to participate in this town function they agreed to the risk of Dean being outbid. If Dean can’t handle someone outbidding him and Rory following the procedure then he should have asked Rory if they could skip the is particular function. They shouldn’t just rage quit because Dean lost.
Clearly they didn’t anticipate Jess outbidding Dean, but that was a risk they adopted when they decided to play.