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A young woman from a privileged life falls for a soup-kitchen owner after discovering a Dear Santa letter written by his 7-year-old daughter.

A busy single mom tasked with organizing her city's Christmas parade discovers an antique sleigh which seems to have a mind of its own.

An accountant, who never quite grew out of his awkward teenage years, finds himself with a dating coach - she happens to be his high school crush as well. Thanks to his coach, he gets a pretty woman he has his sights on for some time, but realizes they are incompatible. Meanwhile, his dating lessons with his teenage crush reawaken old feelings. Not realizing the feelings are mutual, he finds himself unable to act on them due to his fear of being rejected by the one he truly loves.

Lucy wasn't sure if she would find true love, until Jack moves to town with his daughter Sophie. Together they teach her it's never too late to start chasing rainbows.