That aligns with what I think from a story POV with their arc. He gave up his allowance to see her breast, and if you have Marie's path active, Dylan had to steal money from Sophia's purse to pay for the Ice cream. So where did he get this money to spend? The caption said Dylan asked her out on a date, but she would have to pick up the check, plus Dylan doesn't drive, so now Sophia would have to drive, or they would have to take a taxi.
Did he think this out (I highly doubt it)? Because she would have to pay for everything, and As I said, if Marie's path is open, how does he return the money? Because that is supposed to play a role in how the date plays out if the money hasn't been returned. This means where did Dylan get the money because he had to return what he took from Sophia, and Dylan doesn't have an allowance.