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A grieving daughter discovers a red envelope from her mom that contains a final request: for her to complete a Christmas Checklist of twelve activities before Christmas, the last one being “Find Love”.

Dennis and Henry are neighbors and both married their high school sweethearts. When they both get divorced at the same time for different reasons, Henry and Dennis lives turn upside down as they get back into the dating world and on with their lives after they receive a To-Do list from an old friend.