A week or so before school is to start, Diana invites Anne and a few other friends to her birthday party. The gathering is fun, but toward the end the girls grow a little bored and decide to play a game called Dare. This game has gained popularity in Avonlea that summer, spreading through the boys’ groups and eventually making its way to the girls, such as those at Diana’s party.

First Carrie Sloane dares Ruby Gillis to climb an old willow tree. Ruby, who worries more about tearing her dress than falling down, accomplishes the task to Carrie’s dismay. Then Josie Pye dares Jane Andrews to hop on one foot all the way around the garden without stopping or putting her other foot down on the ground. Jane fails at this feat. When Josie starts to gloat about her victory over Jane, Anne defends Jane by daring Josie to walk along the top of the board fence that circles one of the fields. Josie completes her dare successfully—and she does it with the air that the challenge was barely worth her time. When Josie climbs down from the fence, she is met with reluctant applause. Josie is not one of the more popular girls at the party. However, she has just accomplished a feat most of the other girls at the party could not have done.

Sensing a building tension between herself and Anne, Josie looks defiantly at Anne, waiting for Anne’s approval. Instead, Anne states that walking a board fence is a simple dare. She has known many girls who have accomplished it. Anne implies that it would take more than that to impress her. To make this point clear, Anne declares that she knew a girl who walked the ridgepole of a roof (the horizontal beam across the top of a roof). Josie immediately says she does not believe this. In fact, Josie does not believe anyone could do that, especially Anne.

This infuriates Anne. “Couldn’t I?” Anne retorts. Instead of answering her, Josie responds by challenging Anne to do so right then. Anne cannot back down; she feels she must prove that she is better than Josie is. However, when she climbs up to the top of the roof, she realizes the difficulty of the dare. She is much higher off the ground than she thought she would be, which makes her feel slightly dizzy. On top of that, once she starts tiptoeing across the top, she acknowledges that no matter how big her imagination might be, it will not help her in this situation. Anne tries her best, but upon losing her footing, she tumbles down the slope of the roof and hits the hard ground. Diana’s mother runs out to find that Anne is all right except for a sprained ankle.

Despite her anticipation of going to school and meeting the new female teacher, Anne is greatly disappointed that she must miss the first few weeks of school. She is under doctor’s orders to remain in bed until her ankle heals.