I believe those choices on oct 21 only appear during Akane's route. Complete Chihaya's route to unlock Akane's.
EDIT: I tested it and looks like in addition to unlocking Akane's route, specific choices have to be made prior to 10/21 for it to even appear. For example the quest on 10/21 will not appear unless you select "Go Somewhere Else" on 10/16.
EDIT2: After further testing, I did successfully trigger the 10/21 quest without unlocking Akane's route. So, its more like you have to fulfill the quest conditions in addition to selecting the correct choices.
"Go Somewhere
