She later regrets her decision after being controlled by Lotso and blames herself for Buzz's transformation to demo mode and presumably Woody's so-called death. This causes Jessie and Woody to yell at each other for a brief moment, and later when Woody leaves to return to Andy. But when Andy grows up and the toys assume they were thrown away, Jessie quickly decides to donate themselves to Sunnyside. Over the years with Andy, Jessie and Woody begin to have a much more close relationship. However, several mishaps occur, which were caused by Stinky Pete, and Woody eventually saves Jessie from a plane bound to Japan. They begin to form a strong friendship, and later convinced Jessie and Bullseye to go with him to Andy. Her story makes Woody feel sympathy towards the cowgirl and her story is the reason he decides not to leave, making Jessie happy. Eventually, Jessie opens up to Woody about her past owner Emily and how she was abandoned by her owner. For a while, both of the toys share strong dislike towards each other, and during the night Woody plans to escape, the television happens to turn on, waking Al, and Woody suspects Jessie of using the remote to turn on the T.V so she doesn’t have to go back into storage.

This causes Jessie to dislike Woody as her claustrophobic fears begin to return, as her fear of being put back into storage begins to look like a possible outcome. She, Bullseye, and the Prospector all begin to get along with the cowboy until he reveals that he needs to return home to his owner.

Jessie first meets Woody after being stolen from a yard sale by Al who introduces him to Stinky Pete. The two are shown to have pretty heated arguments from time to time, but they deeply care for each other nonetheless. Since meeting each other in Al's penthouse, the two share a close bond. Woody and Jessie share a sibling-like relationship.

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