The first date is more of a feeler date for Craig, all dialogue options in the beginning give the same response so you can really just ask him questions in whatever order you feel comfortable with. Let’s start with the Bro to end all Bros: Craig (Guides go in order of Craig, Robert, Mat, Hugo, Damien, Brian, then Joseph). Without giving any spoilers away regarding context, here are the dialogue options best suited to achieve that perfect score. In order to achieve the perfect date, the player has to pull out their moviest moves ever and we’ve got just the thing to help out.
Throughout the game, the player has the opportunity to go on three dates with their “Dream Daddy” and the objective is to obtain the highest score ranking possible, the “S” ranking.