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A Tangled Web is one of the few books published by L. M. Montgomery (author of Anne of Green Gables) that was written mainly for adults. It centers around a community consisting mainly of two families, the Penhallows and the Darks, who have intermarried frequently amongst one another.

When the clan matriarch, Aunty Becky Dark, dies, she leaves instructions for a treasured family heirloom, the old Dark jug, to be left in the care of a trustee, with the true heir to be revealed in a year's time. Family fueds intensify, as clan members work to acquire the heirloom.

Tropes used in A Tangled Web include:
  • Abusive Parents: Brian is raised by his neglectful aunt and uncle.
  • All Love Is Unrequited: And how. Aunt Becky's dying confession is that she loved her married friend Crosby all her life; Roger loves Gay, who is engaged to Noel; Joscelyn and Hugh each believe that the other hates them; Murray pines for Thora, an abused wife; Naomi longs for her amnesiac husband to remember her ... plus several more examples that would take too long to write.
  • Big Screwed-Up Family: The Darks and Penhallows.
  • Christmas Cake: Margaret Penhallow, Mercy Penhallow.
  • The Clan
  • Courtly Love: Murray for Thora. Mercilessly parodied with Joscelyn, who left her husband on her wedding night because she fell in Love At First Sight with his best man Frank. She stayed faithful to Frank's memory for ten years without ever seeing him, but when they meet again, guess what? He's fat, bald, sleazy and broke. Joscelyn comes to her senses with a vengeance, goes back to Hugh, and lives happily ever after.
  • Curtains Match the Window: Gay Penhallow has golden-brown hair and golden-brown eyes.
  • Dating What Daddy Hates: Donna and Peter, who belongs to a rival branch of the family.
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Drowned John: "You shall never speak to Peter Penhallow again!"
Donna: "But I'll have to speak to him sometimes, Daddy. One can't live on terms of absolute silence with one's husband, you know."

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"Who would have supposed that Mercy Penhallow, malicious Mercy who was afraid to be out after dark--perhaps for fear of the ghosts of reputations she had slain--could have been a perfect heroine during the terrible Spanish flu epidemic?"

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  • Game Between Heirs: Aunt Becky willed that the name of the heir of a priceless heirloom will only be disclosed a year after her death. Because the will dropped a few hints that a unknown judge would be selecting the heir, the family members spent the rest of the year trying their best to live up to what Aunt Becky would have wanted in an attempt to win the heirloom.
  • Greek Chorus: Pippin and Stanton Grundy.
  • Gossipy Hens
  • Have a Gay Old Time: Poor, poor Gay Penhallow.
  • Her Heart Will Go On: Virginia Powell, a sentimental war widow, parodies this trope.
  • Ho Yay: Roommates Big Sam and Little Sam act an awful lot like an old married couple.
  • In the Blood: Gay's mother questions the suitability of her daughter's fiance based upon his "Gibson blood". A certain branch of the Penhallow family, including Peter and Joscelyn, are known for mood swings and impulsiveness because they're descended from a Spanish woman.
  • Jerkass: Plenty, but Aunt Becky would be the more prominent example.
  • Kissing Cousins: The Darks and Penhallows continue to intermarry very frequently.
  • Known Only By Their Nickname: Gay (Gabrielle); Nan (Hannah); Drowned John; Pippin (Alexander); Dandy (Robert); Penny (Pennycuik); the Moon Man (Oswald); Big Sam and Little Sam; Aunt Becky.
  • Laser-Guided Amnesia: Lawson Dark, due to an injury in the war, can't remember his wife.
  • Loads and Loads of Characters
  • Love At First Sight: Donna and Peter, Joscelyn and Frank (on her side anyway).
  • Love Triangle: Buckets of them.
  • MacGuffin: The jug.
  • Make-up Is Evil: Aunt Becky's wearing rouge shocks her companion, and she makes Nan wash hers off.
  • Male Gaze: Several times, but special mention goes to Murray, who's describes as "devouring" Thora with his eyes.
  • Mama's Baby, Papa's Maybe: Brian. His mother never told, and so no one knows who his father is.
  • May-December Romance: Roger and Gay.
  • Narrative Profanity Filter: Drowned John, "by asterisk and by asterisk".
  • New Old Flame: Joscelyn and Hugh.
  • Never Live It Down: Aunt Becky knows dozens of embarrassing stories to needle her relatives with.
  • Old Flame Fizzle: Used twice, with Joscelyn and Gay
  • Passed Over Inheritance: Without the objections. The narrator points out they are not so petty as to want her moeny; they want the family heirlooms.
  • Runaway Bride: Joscelyn leaves her husband to return to her mother's house on the night of her wedding, still wearing her wedding dress.
  • Slap Slap Kiss: Donna and Peter.
  • Small Name, Big Ego: Penny.
  • Thicker Than Water: The Darks and Penhallows fight quite a bit against themselves, but present an unbroken front to outsiders.
  • Values Dissonance: The last sentence of the books leaves a sour taste in the mouths of modern readers.
  • Will: Aunt Becky willed that the name of the heir of a priceless heirloom will only be disclosed a year after her death. Because the will dropped a few hints that a unknown judge would be selecting the heir, the family members spent the rest of the year trying their best to live up to what Aunt Becky would have wanted in an attempt to win the heirloom.
  • World War I: Referred to. Donna Dark and Virginia Powell lost their husbands in the war. Roger Dark was in the airforce.
  • The Vamp: Nan.
  • Your Cheating Heart: Noel cheats on Gay with her cousin Nan before breaking the engagement.