Maddison invites you to a co-working space. Your goal here is to prove you respect her workflow.
Now go boot up VDateGames, set your Empathy to max, and remember: vdategames maddison walkthrough work
If you are aiming for the joint scene with both Maddison and Lisette, you must distribute points between them during the "Plan" conversation: Maddison invites you to a co-working space