In the context of a growing aging population, characterized by a lack of established digital product thinking models and reliance on singular physical facilities for leisure activities, this study employs user portraits of the elderly to inform the design of entertainment wearable devices. Utilizing experience design as a central methodology, the project introduces head-mounted projection headphones and touch sticks endowed with writing and drawing functionalities as primary product platforms. By synergizing these components, elderly users are immersed in an interactive crossword puzzle game, fostering an engaging and deliberative cognitive experience, thereby addressing specific cognitive and leisure needs within this demographic. This innovative approach offers a promising solution to enhance the digital engagement and cognitive stimulation of elderly individuals.