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Chicago native Emily Jones loves her city, and has dedicated her career to coordinating its beloved Thanksgiving Day parade every year. This year, Emily is hoping for a memorable holiday and anticipating a long-awaited proposal from her long-distance boyfriend Brian. Then, the parade director hires a wealthy development consultant, Henry Williams, to analyze the finances of the parade and increase profits. Immediately writing Henry off as a privileged playboy, Emily worries he will ruin the joyful spirit of the parade, not knowing how much it means to the city like she does. As the two are forced to work together to pull off a successful production, Emily is determined to show Henry shes in charge. But when Emily suffers a sudden setback, she starts to rely on Henry to help her through it, and suddenly realizes she might be falling for him. As Thanksgiving draws nearer, can Emily confess her true feelings and end the feud while still putting on the parade of her dreams?
Emily Jones has a clear view of her future, including what the situation will be like when her boyfriend of five years, marine biologist Brian, who has been away at sea for three years, will ask her "the big question" on November 15th, the day after his scheduled return to Chicago, and what will be the happiest day of her life when they get married. The one issue with Brian she does not yet see in that clear view is her phobia of being on a boat, she never having stepped foot on one in that fear. She is also a traditionalist, which in part is why she solely wears vintage clothes from the 1950s, most pieces from her best friend Jaclyns store. Thats also why she loves her job as an operations manager for the city, as one of her major responsibilities is to oversee the citys annual Thanksgiving Day Parade, which she sees as providing lasting memories for anyone watching it. So she isnt too happy when her boss Paul tells her that the city has hired a consultant to evaluate the revenue generating prospects of the parade, she fearing it will lose its traditions in focusing on the bottom line. She is even more concerned when she sees that consultant is Henry Williams, a businessman with who she had a less than pleasant earlier encounter in he having purchased a heritage commercial building in Chicago which he is demolishing to build yet another modern monolith. In he presenting himself as a man of wealthy perfection, she can see that he is a bottom-line kind of guy with little thought of tradition or history. Her view of him is strengthened when she discovers that he considers himself to have no "home"; he travels with those few possessions he considers necessary, so has no touchstones of a past. In spending time together, both Emily and Henry soften their opinions of each other while realizing that their own lives arent quite what they thought they were. As they start to fall for each other, Emily must figure out how it plays into that clear future she sees with Brian, and Henry must decide he is willing to settle down, something he has never seen in that imbalance between work and life.
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