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Penelope was Tarquin's ninth wife, having married him while he was serving in the Empire of Blood.

15 years prior to the Order of the Stick's arrival on the Western Continent, Penelope had fallen in love with a street illusionist. After a whirlwind courtship, they married and she gave birth to a baby girl. One morning, shortly after her baby was weaned, both her husband and daughter had disappeared along with the contents of her family's coffers. For years, she searched for her daughter, but she never found her. Divination was of no use and they couldn't find her daughter's location, but they managed to discover that her husband had married her under an alias, and revealed his true name: Orrin Draketooth. She later married Tarquin, and for his birthday just before she passed away she gifted him a Ring of True Seeing.

When her stepson Nale was searching for the location of the gates holding the Snarl, he had Sabine pose as a new fortune teller in town. Having already learned about her stories about Draketooth from one of many nights where she got drunk and wouldn't stop talking about it, he used her connection to Orrin to strengthen Zz'dtri's divinations. With a "new friend", presumed to be Sabine in disguise, she planned to uncover a lead on Draketooth and find her daughter. Over the next several months, the Linear Guild's divinations managed to eliminate every possible location on the continent for the Draketooths to hide except for Windy Canyon.

With Draketooth's location, she planned to hire adventures to go after Nale until she died under "mysterious circumstances". The truth was that she was killed when Vaarsuvius used Familicide, as she was related to the Draketooth Family by marriage and by bearing one of their children. She was buried in a state funeral a week before Elan and the Order arrived in Bleedingham.

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