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Winner of the Jury Prize at the Art of Brooklyn Film Festival and official selections at Hoboken International Film Festival and the Chelsea International Film Festival, How To Say Goodbye is a personal story by the filmmaker. Tom is a down-and-out bond broker struggling to keep his business afloat, a legacy of his brother who passed away on 9/11. Claire is a fledgling actress from a small town starting over after a personal tragedy of her own. As their lives cross, Tom must face the decision to let go of his fears and acknowledge deeper feelings for Claire or withdraw to his comfort zone. Tom's best friend, Simone, has an identity crisis and an appetite for short-term gratification. Mario, Tom's wing man and a wine enthusiast, must contend with trappings that come with being a womanizer. In the urban maze of New York, the four struggle to say goodbye to old ways to find a better tomorrow.