After noticing Rory has seemed tired and distracted for a few days, Max says he’s concerned about her. He lets her know that he is sympathetic that she broke up with her boyfriend, and that he is available to talk if she wants to.
All this comes as the most terrible shock to Rory. She learns that her mother and Max got back together weeks ago, and have been talking regularly for at least three weeks – including discussing her personal life. Coming just after finding Lane and Dean studying together and talking about her, this seems like another betrayal – but even worse, because it is her mother.
Max behaves in a fairly inappropriate way here. He means well, but he approaches Rory more as a prospective stepfather than a teacher by wanting to talk about her breaking up with her boyfriend. Rory has really only been in a miserable mood for a few days, and it hasn’t impacted on her schoolwork yet, so there isn’t any need to do this.
Max shouldn’t be discussing her personal life at school, and should have checked with Lorelai before telling Rory that he and her mother are back together. He is being rather presumptuous by taking on a stepfather role at this stage – he and Lorelai haven’t even been on one date together since breaking up months ago!