The Engagement Ring begins with the history of the Di
Cenzos and the Rosas, two Napa Valley families intertwined by their friendships and their passion for winemaking. Nick Di Cenzo (Tony Lo Bianco) and Alicia Rosa (Lainie Kazan) were playmates as children, first loves as teenagers and later the source of a permanent rift between the two families.

While serving overseas in the Army, Nick mailed an engagement ring to Alicia that he'd won in a poker game. When no answer came, he never contacted her again, his ego bruised by the rejection. Unfortunately, the ring was never delivered. As a result, Alicia also was heartbroken, interpreting Nick's silence to mean he'd found another love. Though Nick remained a carefree bachelor, Alicia married Johnny Anselmi (Chuck Shamata), who had adored her ever since he worked in her father's vineyard as a child.

Forty years later, Alicia and Johnny's daughter, Sara (Patricia Heaton), and her fiance, Brian (David Hunt), try to negotiate a deal between the two feuding families, so they can create a new wine to further the tradition of her family's vineyard. But matters become further complicated when the long-lost ring and marriage proposal finally find their way to Alicia.

In her quest to heal the ancestral wound, Sara finds an unexpected ally in Nick's nephew, Tony (Vincent Spano). Together they make plans for a reconciliatory lunch between the two former loves in hopes of getting them to agree to merge the two vineyards. As the two create a traditional Italian feast, they stumble upon the meaning of love, friendship and living life to its fullest.