In ‘They Shoot Gilmores, Don’t They?‘, Dean comes to say hi to Rory while she’s at the dance marathon. Jess & Shane are there watching, and Jess makes sure Dean sees that. Jess stays for 8 hours watching Rory – or pissing off Dean – until Dean has enough. He doesn’t want to be Rory’s “pawn” against Jess, which I think is what he feels like.
When Rory later tries to complain to Dean about Jess being there and bugging her – particularly the making out – Dean has obviously had enough. When Jess & Rory fight about him being there, right in front of Dean, Dean simply says “I’m not her boyfriend anymore.” He knows Rory doesn’t want to be with him, though she says she does, and that she really wants to be with Jess. He’s giving her the freedom for that.
Later, when Jess comes to see if Rory is ok, Rory admits everything is true – about how she feels about him. Jess agrees. So, what I want to know is, why did Rory string Dean along like that? If she knew she had feelings for Jess, was it fair to Dean to treat him like that? Should she have broken up with him, even if Jess was not interested in her in return?
What stopped Rory from breaking up with Dean?
Watch this episode of Gilmore Girls on TheWB.com here.