Lorelai needing her rain gutters cleaned was mentioned in “A-Tisket, A-Tasket” – she was hoping that the “Collins kid” might clean them for her. Luke remembers this, and suggests Jess could clean her gutters instead. Lorelai puts him off by saying she’s already got people lined up for the job.
Rory puts her head down sadly or sullenly when Lorelai balks at Jess coming to their house. Note that Rory is holding the ice creams hugged close to her chest, so her body heat will melt them even faster. I’m pretty sure that’s not ice cream in those cups marked “ice cream”.
The Annotated Gilmore Girls 