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What happens at book club doesn't necessarily stay at book club. Welcome to Fortuna, Texas where the men are dared to love as big as they live. The men of widower Brad Davidson's book club, the Fortuna Dare Society, are dared to act out a trope, setting, and character with a significant other. That poses a problem for Brad, who hasn't had serious relationship in over 20 years. He likes the town librarian, but it might not amount to anything more than a strange, costume-staged, musically-enhanced meal. Then again, he married the last woman he went out of his way to date.

Under the guise of saving her best friend's marriage, Annie Harper catches the red-eye out of LAX to Oahu. Less than 24 hours after hearing Marissa wanted to kiss their old high school crush, Annie sails away with the handsome owner of the Erika Rose excursion boat. She only meant to keep Terence Javier from locking lips with Marissa, but the moment she learns his little girl needs an advocate, Annie brings her friend back into the fray and destroys the remnants of Marissa's anniversary vacation.