Maddison will eventually open up about a past struggle. Do not make a joke. Offer support and "Validate" her feelings. This unlocks the deeper, more intimate levels of her story.

This walkthrough will guide you through the key choices and requirements to master Maddison’s route. Getting Started: Maddison’s Profile

If a dialogue option is locked (greyed out), it means your Charm or Intelligence isn't high enough. Spend a few in-game days "working" or "studying" to boost these.

Always prioritize "Flirty" options over "Friendly" options once you pass the second date. Conclusion