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Alex and the Ironic Gentleman by Adrienne Kress, published in 2007.

Often mistaken for a boy because of her haircut and name, Alex Morningside is an inquisitive girl of ten-and-a-half who attends the prestigious Wigpowder-Steele Academy. Unfortunately, though she loves to learn, Alex just can’t bring herself to enjoy her classes. Her teachers are all old and smelly and don’t seem to know about anything that has happened in the world the past thirty years, and her peers…well they are quite simply ridiculous.

Luckily for Alex, the new school year brings an exciting new teacher. Mr. Underwood makes lessons fun and teaches her how to fence. But Mr. Underwood has a mysterious family secret—the swashbuckling and buried treasure kind—and not everyone is glad he has come to Wigpowder-Steele. When the infamous pirates of a ship called the Ironic Gentleman kidnap Mr. Underwood, Alex sets off on a journey to rescue him, along the way encountering a cast of strange and magical characters, including the dashing and sometimes heroic Captain Magnanimous, Coriander the Conjurer, the Extremely Ginormous Octopus, and the wicked Daughters of the Founding Fathers’ Preservation Society.

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There is a sort-of sequel to it, Timothy And The Dragons Gate.


This book contains examples of:

  • Adorkable: Mr. Underwood.
  • Affably Evil: For a time, Captain Steele is fairly friendly towards Alex and welcomes her to the crew.
  • Artificial Intelligence: The MakeCold fridge, in addition to being able to remember recipes, monitor the foods inside of it, and water plants with a spray apparatus, is also capable of lying, dreaming of alternate careers, and developing a fondness for boyish girls named Alex.
  • Character Name and the Noun Phrase: Alex and the Ironic Gentleman
  • Chekhov's Skill: Mr. Underwood teaches his students fencing, and how to correctly use the pronouns "I" and "me". Both become important later.
  • Conveniently an Orphan: Alex has neither mom nor dad.
  • Determinator/Super-Persistent Predator: Daughters of the Founding Fathers' Preservation Society track Alex halfway across the world because she crossed the velvet rope.
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  • Distressed Dude: Mr. Underwood is kidnapped by pirates.
  • Exactly What It Says on the Tin: The Extremely Ginormous Octopus, who is an extremely ginormous octopus.
  • Felony Misdemeanor: Alex spending most of the book repeatedly running away from the same implacable pursuers a bunch of little old ladies who want vengeance because she stepped over the velvet ropes in a museum.
  • For the Evulz: Charles, the villain of the train, does what he does because he likes to be evil.
  • Gender-Blender Name: As stated before, Alex.
  • Going Down with the Ship: Captain Magnanimous and his crew.
  • "Groundhog Day" Loop: When Alex gets on the train, she seems to be caught in an endless loop of party, drink, dance, eat, sleep for ten minutes, repeat. With every loop, someone disappears, and nobody remembers them….
  • I Will Find You: Alex will stop at nothing to track down her dear friend and English teacher.
  • Lady Looks Like a Dude:
    • It is repeatedly remarked upon how many people confuse Alexandra "Alex" Morningside for a boy due to her name and her short haircut.
    • The dreaded—yet female—Captain Steele, however, is assumed to be male solely because of her reputation.
  • Large Ham: The aging actor Extremely Ginormous Octopus is hammier than a barn full of pigs.
  • Meaningful Name: Lord Poppinjay the vain, rich man. Captain Magnanimous the… magnanimous captain. “Senseless” Senslesky.
  • Names to Run Away from Really Fast: Captain Steele the Inevitable
  • Never Mess with Granny: While the Daughters of the Founding Fathers’ Preservation Society may seem like vaguely nasty but overall harmless biddies, they are actually extremely dangerous—managing to track Alex halfway across the world and even force evil pirates to do their bidding.
  • Pirate: There are several, notably the crew of the Ironic Gentleman.
  • Telepathy: This is how Lord Poppinjay attempts to communicate with his staff, much to their bewilderment. Alex is able to “communicate” back by offering suggestions as to the course of action, but phrasing it as though it was Poppinjay’s idea. He confirms that of course, that is exactly what he was thinking.
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