In this time of questions and reflections, experimentation becomes a question capable of creating new dialogues, so a famous quote stimulates comparisons where design translates possibilities and art narrates new visions. How Might We is one of the methodologies used by​ D​ esign Thinking to generate, through short questions, a brainstorming capable of amplifying creativity. This method has been the starting point for HOW MIGHT WE - Short quotes inspiring relations between art and design, with the desire to investigate different languages ​​that can build new imaginaries. Starting from reflections generated by the quotes of three famous designers, symbolic spaces welcome the works of three contemporary artists, confirming the ability of art to create meanings and offer access keys to the interpretation of the world in which we live.