Drawing Pal is an empathetic drawing machine designed to explore the emotional and rhythmic connection between a human and an artificial being through outdoor sketching. Installed with wearable sensors—such as potentiometers—attached to the artist's arm, the system captures natural drawing gestures. These motions are translated in real-time to a robotic drawing arm, which either synchronizes with or interprets the artist’s drawing movements. This project is aimed not only at self-healing and a reconnection with the surrounding environment, but also at rediscovering the joy of drawing through shared experience, co-creation, and expressive interaction with a mechanical companion. Rather than producing technically perfect graphics, the focus is on building a poetic and intuitive dialogue between human and machine.