The exclusive content in VDateGames is often hidden behind specific "Key Items" or timed events. For Maddison, you need the "Silver Locket" which can be purchased from the in-game shop after the second week. The Weekend Getaway Event
When there is an opportunity to join her, say, "Maybe I should come, too" (+1 Maddison). Office Discussion: vdategames maddison walkthrough exclusive