Winnie Bosko / COLD FRONT

As a child, Winnie was shown to be incredibly shy, timid, and wary of others and their actions, particularly when a younger Augustine approached him. Nevertheless, with Augustine's words of encouragement, Winnie drew inspiration from Augustine's attitude, gradually adopting similar traits during his early years.

As Winnie grew older, he displayed obvious similarities to the younger Augustine - bubbly, cheerful and optimistic. Winnie often approached situations with a lighthearted perspective, not taking them as seriously as Augustine did, as seen when he built a snowman during a blizzard while Augustine focused on looking for useful items in the car. Despite this carefree attitude, Winnie demonstrates a keen analytical ability, making deductions about their surroundings, such as sudden clothing changes and peculiar settings. Additionally, Winnie consistently prioritized Augustine's needs over his own, refusing to burden Augustine when offered to carry him due to Winnie being unable to handle the cold of the blizzard. As the narrative unfolds towards the conclusion in the good route, Winnie is shown to be very understanding of Augustine, and open minded to what he tells him.

Though not included in the game, the creator has stated that Winnie doesn't understand boundaries, he would make jokes or share information about Augustine that he would feel too personal about, he doesn't do it on purpose as he simply believe that is just what close friends do, not realising how he had hurt him.