At the 25th Annual Gilbert family reunion, siblings Gil, Dil, and Lil compete for the coveted Gilbert Cup.

Growing up poor on the streets of New Jersey, Frank Siena (Danny Nucci) has little hope of realizing his dream of becoming a doctor. But "fate" has a way of intervening. Now a brilliant, successful cardiac surgeon, Frank seems to have it all, except for one terrible secret: Before he swore to save lives and do no harm, Frank took another oath... to mob boss Nicola Delarusso (Paul Sorvino), who paid his way through medical school in exchange for absolute loyalty. And when Delarusso demands payment in full Frank suffers a crisis of conscience that could cost him his job, his wife... and his life!

The story of Gloria, a worldly but crabby teen-boy-band manager and Sherman, a morose rural man as they escape from their lives, experience life-changing travel, and against their will, cling to one another. When they fall in love for the first time, it's an impossible situation, because you can't just change your life overnight. Can you?