Conversations with Unexpected Guests is a memoir constructed from a series of portraits, paired with conversations, between the artist, Ann Dunne and the person in the portrait. They engage in lively exchanges on a variety of topics, including aging, creativity, adjusting to life's challenges, hopes, dreams, and fears. The conversations reveal the person in the portrait and also reveal the author's interest in exploring what the portrait has to say. Echoing a quasi Gestalt approach that employs active imagination and projection. The artist/author's active imagination of her conversations is a give and take. She asks questions about the portrait, which gives a response. It becomes an intimate exchange of asking, listening and response. The moods and topics change with each encounter. The conversations show audacity, courage, and curiosity, an honesty in reaching for the truth within the Self. As we get to know the "guest, " we understand Dunne is fearlessly speaking about what supports our development as honest, vulnerable, and compassionate human beings. Dunne's exercise of connecting with the depth psychology archetype clarifies views on aging, the creative process, life's challenges, and social justice. Her concerns for survival, her compassions, and courageous curiosity is apparent. Life changes us. It offers opportunities and choices for development. Ultimately, Dunne maintains curiosity is an essential tool for good enough outcomes. We can do this by continuing to ask out questions throughout life.