A ​Tangled Web is a novel by L. M. Montgomery. It is one of the few books she published that was written mainly for adults. It centers around a community consisting mainly of two families, the Penhallows and the Darks. For several generations everyone in the Penhallow family has married someone in the Dark family.

Aunt Becky has died and in her will left a prized family heirloom to a person to be disclosed in one year’s time. In the year that follows, the family members try their best to live up to what Aunt Becky would have wanted in an attempt to win the heirloom, and in the process, many achieve self-discovery. There are several intertwining stories, but the most important ones involve the following characters:

Young Gay Penhallow’s fiance, the shallow Noel Gibson, dumps her for Nan Penhallow, a devious and deceptive girl. Although she still pines for Noel, Gay begins a relationship with Dr. Roger Penhallow, her fourth cousin. Gay slowly matures as she and Roger get closer. When Noel attempts to return to Gay, she realizes that her infatuation with him pales next to her true love for Roger.

Donna Dark and Peter Penhallow, who have despised each other since childhood, suddenly fall in love. They immediately make plans to get married, but their rival families soon discover their relationship. Although Donna and Peter resist attempts to break them up, the relationship ends during an argument on the night they were supposed to elope. The couple remains estranged until Peter saves Donna from a fire. They then get married and leave for Africa.

Joscelyn and Hugh Dark were separated on their wedding night, when Joscelyn confessed that she was in love with Hugh’s best man, Frank Dark. The remain separated for ten years until Frank returns and Joscelyn realizes that he was not worth the passion she felt for him. She regrets her decision to leave Hugh until Hugh is in a car accident and call out her name. After a confrontation with Hugh’s mother, Joscelyn realizes that she loves Hugh and she returns to him

Margaret Penhallow, the family dressmaker and old maid, agrees to marry Penny Dark in order to improve both of their chances of getting the jug. Although she is not very fond of Penny, Margaret longs for a home of her own. Penny, similarly, has doubts about the match and enjoys being a bachelor. After an incident in which Penny drunkenly woos Margaret, he decides to break the engagement. He then becomes resentful at Margaret’s joy over her “jilting.” Margaret then decides to sell a rare version of The Pilgrim’s Progress that she inherited from Aunt Becky and uses the money to buy a house for herself and to adopt Brian, an illegitimate and lonely orphan who is largely neglected by the family.

In the end, Dandy Dark, the person in charge of the jug, confesses to the family at large that he has lost Aunt Becky’s instructions for selecting the new owner of the jug. As the family prepares to argue over the jug, the Moon Man, the eccentric Oswald Dark, destroys it.

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