A wealthy and popular entrepreneur hires Chance Hazelton, owner of a struggling shop called Gifts by Chance, to help him organize a perfect proposal for his girlfriend.

When Zoe Williams has to prove to a big investor that her company's new dating app works, she tests it on herself and soon ends up on a date with her complete opposite, Oliver Beckett, an easygoing, spontaneous artist. Huh. Not exactly Zoe's type. Even though it's clear the pair have chemistry, Zoe's worried- could something be wrong with DigiLove's algorithm? Or is it true when people say "opposites attract"?

Mandy Leeds (Jonna Walsh), a successful young woman living in Miami, is climbing her way up the corporate ladder in the hotel industry. Though she doesn’t get back to her small northern hometown much, this year her Gram (Jayne Eastwood) is able to finally convince her to come home for Christmas. Mandy has another reason too – the quaint local inn is for sale, and she wants to acquire it for her company. With her eyes on the prize, Mandy travels back home but on her way there, she runs into Lucas Menzino (Jesse Hutch) — her high school rival — who also has his eye on the inn as well.