Webb is shown to be a calm and a respectful individual with a carefree personality. He maintains a positive impression with people he meets and often hangs out with his friends, Brick, Cole, and Tyler. Webb is described as an expert in landscapes, since he grew in a family farm. He relies on the winds, and shadows of the forest to figure what direction to go. And sometimes, relies on the clouded sky, whenever the sun doesn't shine. Despite his cool demeanor, Webb likes to joke around alongside Tyler sometimes, but it can be useful in Pokémon battles to tick the opposing trainers off.