A Tangled Web is one of the few books published by L. M. Montgomery 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 feuds intensify, as clan members work to acquire the heirloom, and many other events spawn off from it.
This work includes examples of:
- Abusive Parents: Brian is raised by his neglectful aunt and uncle.
- Age-Gap Romance: Roger pines for Gay Penhallow. He's a respected doctor who served in the Great War, while Gay is a carefree young woman still blushing over her first kiss.
- All Love Is Unrequited: 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.
- Alpha Bitch: Nan, who has gone out her way to hurt her cousin Gay since childhood.
- Betty and Veronica: Gay, who is good-natured and doesn't go out of her way to make trouble, and Nan, who loves to make a scene and wears scandalous amounts of makeup and clothes (too much and too little, respectively).
- Big, Screwed-Up Family: The Darks and Penhallows.
- The Clan: The Darks and the Penhallows. Not only do they intermarry one another, quarrel with one another, and stand up against outsiders, but they have a proud family history, of which the jug is an important part.
- Cool Old Lady: Montgomery loved this character type, and Aunt Becky is a rather sinister example. She freely speaks her mind and calls out hypocrisy— to the extent that her wit hurts and humiliates people. To the characters in the book, Aunt Becky is a terror. To the readers, though, she's very fun.
- 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.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. - Disproportionate Reward: Aunt Becky gives her diamond ring to her serving woman, Ambrosine. The rest of the clan thinks this is an absurd act of generosity (and that the ring should have stayed in the family!) The narrator leaves it ambiguous if Aunt Becky did this out of kindness or mischief.
- Domestic Abuse: Chris Dark is an abusive husband to his wife Thora.
- Ensemble Cast: There is no one main character.
- Fourth-Date Marriage: Lawson and Naomi had a brief courtship before they married and he went off to the Great War. This might account for his Laser-Guided Amnesia.
- 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 she said that the heir may or may not be chosen in the year between her death and the day the heir is announced, the family members spend 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, especially during Aunt Becky's levee, the first scene.
- Gossipy Hens: A huge chunk of the cast, both female (Joscelyn's mother and Aunt Rachel, for instance) and male (Pippin and Stanton Grundy, snarking off together during the levee).
- Have a Gay Old Time: Gay Penhallow, of course. (It's actually short for "Gabrielle".)
- Funnily enough, her cousin Nan comes at this trope from another angle: She hates being called her birth name, Hannah, because she wants to be seen as modern. Nowadays the name "Nan" comes off as hopelessly dowdy.
- Her Heart Will Go On: Virginia Powell, a sentimental war widow, parodies this trope.
- 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.
- Ironic Nickname: Big Sam, Little Sam — though not intentionally. It so happens that Big Sam is the older of the two, so the name stuck, even though he's much shorter.
- Jerkass: Plenty, but Aunt Becky would be the more prominent example.
- Kick the Dog: Brian's uncle who kills Cricket, a stray cat who is Brian's only companion, by breaking its neck.
- Kissing Cousins: The Darks and Penhallows continue to intermarry very frequently.
- Laser-Guided Amnesia: Lawson Dark, due to an injury in the war, can't remember his wife.
- Love at First Sight: Donna and Peter, Joscelyn and Frank (on her side anyway).
- Love Triangle: Buckets of them.
- MacGuffin: The jug. The narrator points out that, objectively, it's rather ugly. But it has huge sentimental value for the clan, and may have monetary value based on its age.
- Makeup 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.
- Meaningful Funeral: Despite the hell that Aunt Becky kicked up at her levee, her funeral is a surprisingly quiet, even touching affair. Well, up until a fistfight breaks out over the jug. But even that was at least after the service.
- Narrative Profanity Filter: Drowned John, "by asterisk and by asterisk".
- Old Flame Fizzle: Used twice, with Gay (who, after a year of character development, realizes she's outgrown her first love) and Joscelyn (who was always Loving a Shadow).
- Old Maid: Many examples, but the most notable is Margaret Penhallow. A meek soul who's gifted with a needle, she's never had a beau and everyone looks down on her, especially because she's rumored to write poetry in her spare time. Penny Dark courts her, and she agrees to marry him, but they end up breaking it off. Margaret ends up very happily, in fact, single as ever, but with a house of her own and a child to love (Brian Dark).
- Once Done, Never Forgotten: Aunt Becky knows dozens of embarrassing stories to needle her relatives with.
- Only Known 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.
- Orphan's Ordeal: Brian. He was born out of wedlock and his mother died in childbirth; he lives with relatives who despise him. In the end, Margaret Penhallow adopts him and they live happily ever after.
- Passed-Over Inheritance: Without the objections. The narrator points out they are not so petty as to want her money; they want the family heirlooms.
- Even aside from the jug, Aunt Becky arranges matters so that almost no-one gets something they want. The second-most coveted heirloom is a beautiful diamond ring which goes... to Aunt Becky's serving woman. An act to irk The Clan? Or a grand gesture of kindness? Both?
- Paranoia Gambit: Aunt Becky runs a very successful one, post-mortem. She says that the inheritor of her jug might be named in the envelope, or the envelope might contain a list of instructions and behaviors that Aunt Becky approves of, and Dandy (the keeper of the envelope) is to choose who will inherit the jug based on who has best fulfilled Aunt Becky's wishes. Then, the whole clan spends the rest of the year trying hard to behave in such a way as will guarantee their getting the jug.
- "The Reason You Suck" Speech: Gay gives this speech to Nan when Nan comes to gloat about dumping the fiance she had originally stolen from Gay.
- Runaway Bride: Joscelyn leaves her husband to return to her mother's house on the night of her wedding, still wearing her wedding dress. He won't take her back until she returns to him in that same gown.
- Second Love: Peter becomes this for Donna, a widow.
- Also, it turns out Aunt Becky's own husband, Theodore, was her second love. She was mad about Crosby, who only saw her as a friend, so eventually (after she married him, mind you) she resigned herself to Theodore and was at least decently happy.
- Secret-Keeper: Dandy Dark, chosen because Aunt Becky said he's the only person in the whole family that she's known to be able to keep a secret. He keeps it so well, in fact, that even he never opens the envelope to read her will. And then the letter is lost, so this trope is Subverted.
- After ten years of utter silence, Joscelyn ends up telling Aunt Becky why, exactly, she left her husband. It is a confidence to the grave itself.
- Slap-Slap-Kiss: Donna and Peter. Their wooing alternates between passionate kisses and equally passionate spats.
- Small Name, Big Ego: Penny considers himself a wit and God's gift to women. He is neither.
- Dandy Dark puts on airs when Becky makes him the jug's trustee. Up until then he had been rather obscure.
- Thicker Than Water: The Darks and Penhallows fight quite a bit against themselves, but present an unbroken front to outsiders.
- The Unreveal: Dandy loses Aunt Becky's letter and we never get to find out who was chosen as the rightful owner of the jug.
- The Vamp: Nan. Aunt Becky observes that with her makeup, she looks like she's been making a meal of blood.
