Danny, a successful plastic surgeon, pretends to be unhappily married to avoid committing to relationships. When he meets Palmer, a beautiful woman, he believes she might be the one and abandons his old tactics. However, Palmer finds his fake wedding ring and assumes he is married. To keep the budding relationship intact, Danny fabricates a story about an impending divorce and convinces his loyal assistant, Katherine, to pose as his soon-to-be ex-wife.

Things spiral out of control when Katherine's kids become part of the deception, and Danny ends up inviting everyone on a lavish trip to Hawaii to continue the ruse. During the vacation, the tangled web of lies starts to unravel as Danny, Katherine, and Palmer become entwined in increasingly awkward situations. The trip forces Danny to confront his true feelings and reconsider his approach to love and relationships, leading to unexpected connections and revelations.