Some responses now have a 5-second timer. Don't overthink; the middle option is usually the "safe" Trust builder.
If she asks about your past, choose the "vulnerable" dialogue options. vdategames maddison walkthrough upd
To succeed with Maddison, you must balance three primary bars: Increases through listening and kindness. Lust: Increases through bold choices and physical contact. Some responses now have a 5-second timer