Their relationship first began began in The Vow when John returned to Salem where Anne later develops a fatal attraction to the captain, much to the dislike of her father and Mary Sibley.
Throughout the first series John often comes to Anne's rescue and the pair soon develop a friendship.
In Our Own Private America the pair share a passionate kiss due to John being under Mary Sibley's dream spell but it is unknown if her feelings are actually reciprocated or if they could become a possible romantic pairing in the future. They are portrayed by Tamzin Merchant and Shane West.
Anne first meets John in The Vow at the dinner party hosted by Mary Sibley, where she shows to have an obvious attraction towards him, which does not go unnoticed by those present. She later appears as an illusion created by Mary caressing the captain provocatively under the table. The next day John stumbles into Anne at the graveyard where she is sketching and she flirtatiously jokes with the captain, she asks if she can draw him sometime but he informs her he is leaving Salem for New York.
In The Stone Child following Bridget Bishops death, she attacks Cotton but is stopped by John who comforts her in her grief. The same night she confronts John in the tavern and ask why he is still in Salem and has done nothing to stop the persecutions that has took the lives of both their friends convincing him to stay in Salem.
In In Vain while the body of Bridget Bishop is been taken to the crag thieves break into the orphanage while Anne tries to protect the children but is saved by John when he hears her cries for help. She asks the captain to escort her home and is devastated to learn from him in how bad the crag is and that is the final resting place for her dear friend.
After her sudden illness she once again stumbles into the captain at the graveyard in Survivors where he is visiting his parents grave. She tells him of her fears that her illness may of been something else despite her fathers reassurances, leading John to suspect her father is a Witch. That night she flirtatiously greets the captain at his reception to the selectmen board and after returning home, her father questions her on her feelings for him, warning her to stay away from him as he will only break her heart as he is still in love with Mary Sibley.
In Lies having been warned from having any more contact with the captain from her father, a disheartened Anne questions a bewildered John in the market but the pair are interrupted by Mary Sibley.
In Departures Anne visits the captain. She asks to be invited inside his home so she can speak with him privately about her suspicions of her father.
In Children Be Afraid John seeks the help of Anne with the heartbroken Cotton after the banishment of his lover Gloriana Embry. The pair take a drunk Cotton home and she later asks for his assistance with fixing the roof of the orphanage. Where he later takes an interest with a young boy who had seen his family murdered by Indians and had not spoken since he had arrived years earlier. That night John escorts Anne home and she is shocked to learn the captain had learned the boys name was Stephen after spending only one day with him.
In The House Of Pain after Anne's disappearance, Magistrate Hale seeks John's help in recovering his daughter who is lost deep in the woods. They eventually find her miles away from Salem and John asks how she got there with barely leaving any tracks but she remains tight lipped and thanks the captain for his heroism before she kisses him on the cheek. Upon returning to Salem a helpless Anne watches as John is arrested for witchcraft by the selectmen board.
In Ashes Ashes during John's trial Anne is coerced by Increase Mather into revealing that John had kissed her forcefully further damning him.