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Writer Annie Butler (Lancaster) is miserable after she suffers a bad breakup while facing her dead-end job writing user manuals instead of manuscripts. Deciding to envision the life she wants in hopes of making it a reality, Annie writes My George, a fiction novel depicting her dream romance with a perfect imaginary guy named George. She is stunned to receive a letter from high-powered literary agent Della Hendershot (Fox), who wants to publish the book and promote Annie as a debut author at a huge bookseller's expo-alongside George. When Annie admits there is no George, Della, furiously trying to get her way, decides to hire an actor to pose as Annie's boyfriend, much to the dismay of Annie and her family, sister Kate (Stoll) and mom Opal (Strassman). Upset she has to lie about her love life, Annie is relieved when she meets George Munroe (Pardue), the handsome and driven realtor selling Opal's house. Desperate to spark a romance with George to bring the pages of her bestselling novel to life before the expo, Annie discovers her attempts at real-world romance fall flat as she tries to recreate the perfect moments from her book. Meanwhile, Annie is reconnecting with high school pal Henry (Quinn), now a plant nursery owner who she's hired to help spruce up Opal's yard for the sale. It is clear Henry's teenage crush on her has resurfaced, especially to his co-worker Frank (Nunez), who encourages him to make a move. As Henry and Annie start spending more time together, Annie soon finds she may be forcing the love she thought she always wanted-without realizing her true fairy tale ending has been waiting for her all along.