Hard working and talented Manhattan lawyer Hugo Spencer (Ben Lewis), disappointed not to get the position as partner, issues an ultimatum to his boss, George Vogel (Glen Grant) just before he and his BFF since college Madelyn McKay (Ellen Wong), are to head off to Milwaukee to spend Christmas with his long-widowed mother (Fran Drescher) and his brother Aiden Spencer (Chad Connell).
Once
in Milwaukee, Hugo finds that his mother, as part of her role as President of
the Carroll Avenue Neighborhood Association, has assigned them all with 24/7
tasks organizing the annual Christmas Eve Festival at the historic Carroll
Avenue Train Station, which is how Hugo meets Patrick Ryan (Blake Lee) again,
his high school crush, and their repeated interactions eventually lead him to
question if a big promotion is as important to him as he first thought.
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