Olive Cullison has come a long way from big plans and hot dates for Valentine's Day. This year, she's planning to take it easy while visiting her sister's family. With her sister at the hospital to deliver her second baby, Olive gets to attend her kindergarten niece's Valentine's party. Widower, single dad Kirby Owens hasn't been into Valentine's Day for years. He doesn't need Cupid to find love for him; Kirby's happy with his life as Henry's dad. While Olive and Kirby share the opinion that Cupid is downright creepy, both have to admit there seems to be some sort of magic at play when the two meet at the classroom mailbox and end up spending the day together. Will their special day just be a fun memory to share, or is it possible Cupid's aim for the two of them was perfect?