As Valentine's Day nears, a matchmaker is tasked by her mentor to find a match for an entrepreneur who believes staying single is the key to success.

A marketing executive makes a trip back home to sell the Christmas gift shop she inherited from her grandfather.

After being dumped by her boyfriend, a successful tech wiz dating-app creator returns to her hometown for the holiday season, and her dad gets her to sign up for the annual Christmas Cupid anonymous matchmaking event.