When self-made spinster in training Lili Alster hires klutzy LoveMatch escort Hal Kessler to pose as her fiancé during her grandparents' anniversary celebration, it's not to impress her family. She plans an explosive breakup to convince them she's really better off staying single.

Desperate for the money and well-aware this could be his last chance to keep his job, Hal enthusiastically tries to act like the utter jerk Lili needs him to be. As Hal's fumbling feet lead them into mishap after misadventure, Lili finds herself stumbling along beside him...right into love.