The film begins with Matt Taylor proposing to his fiancée Heather, who is captivated by the romantic dream of a Roman destination wedding. On the morning of the wedding, Heather flees, leaving only a handwritten 'Dear John' letter.
Matt decides to take the non-refundable honeymoon tour alone. While traveling through Rome, he meets local café owner Gia. In a pivotal plot twist, it is revealed that Gia herself had translated and written the breakup letter for an anxious American woman (Heather) the morning before the wedding, completely unaware of the groom's identity.
When Gia's family café faces imminent bankruptcy, Matt and his tour companions (Julian, Meghan, and Neil) rally to revitalize the establishment and host a community event featuring a musical performance by Gia’s uncle (Andrea Bocelli). Having released his past pain, Matt confesses his feelings to Gia. The epilogue shows Matt happily settled in Italy, while a mid-credits scene features Julian proposing to Meghan for a fourth time.