Cara and Ben head back to the charming resort where their romance blossomed a year ago, this time bringing her friend Megan along to spark a connection with Sean, Ben's friend and the resort's doctor. As Cara discovers a jewelry receipt, she becomes excited about a potential proposal from Ben. However, a series of misunderstandings threatens to derail his carefully laid plans, leaving both couples’ futures in question. Will love triumph, or will secrets and miscommunication freeze their chances for happiness?