Madison O’Hara owns a busy event company where she performs as a singing elf for Christmas parties with her best friend Cooper. Her real dream is to be a singer-songwriter and to find the perfect man but things seem to be slipping away when she breaks up with her successful boyfriend Luke. But when a wise Santa suggests perhaps there’s a perfectly ‘Un-Perfect’ match for her right before her eyes, Maddy takes a whole new look at her life and the people in it.
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The clumsy and shy Stanley is a nice fellow, beloved by his colleagues in the office. He has a crush on the gorgeous new-hire Diana, but he has difficulties to get close to her. When Stanley finally invites Diana for a date, he hits the homeless Phil with his Taurus, and his planned night turns upside down.
Through a series of chance encounters, sparks fly between college literature professor Mia and Tony, a headliner at a Manhattan supper club. Unbeknownst to them, Mia’s mother, Marlene, and Tony’s mother, Sofia, are working some maternal matchmaking magic.
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