For the last two years students from Minerva Art Academy in the Netherlands worked on portraits of people with dementia. By making personal connection with their extraordinary models the most personal and poignant portraits came into being. The concluding exhibition offered a first glimpse into the confusing world of mostly alternating moments of clarity and emotion. In our paper we talk about the educational, the social, and the artistic value of this project. The paper is connected to a film that shows the student portraying the people and talking about the influence of the environment on their artistic practice and choices. While the artistic space that surrounds the person makes an encounter possible, it is the freedom and space that a person with dementia takes that establishes it. A person with dementia guarantees the unexpected, the new, and the different, to which the artist has learned to be open.