HeyDear is a memory box that seeks a way to reconnect our past and future in a playful context. It collects our memories and sends them to our future selves. Letters and voice diaries can be stored and turned into paper planes and calls, then pop up at a random time in the future. It creates important moments of self-reflections and self-talks from where we can all thrive. HeyDear turns all of us into playmates with our past and future selves. It allows us to create surprises and unexpected breaks in our lives. It creates a new way of communication with the most difficult person to confront which is ourselves, and opens up more possibilities to perceive our past.