Hugo, a successful New York lawyer, returns to his hometown of Milwaukee for the holidays with his best friend Madelyn. His mother Kate, who is in charge of the local Christmas celebrations, has a surprise in store for him - a reunion with Patrick, Hugo's secret high school crush who has recently returned from Silicon Valley. As they enjoy the festivities together, their attraction is undeniable, but Hugo's promotion to London threatens to tear them apart. Will Hugo choose his career or his newfound love?

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Some movies that have similar genres and were produced around the same time as The Christmas Setup include All of Us Strangers, The Age of Adaline, Passengers, Past Lives, Something from Tiffany's, The Tearsmith.