Billie, an ambitious New York art executive, travels to Rome to purchase a valuable painting. When her fiancé confesses he’s in love with another woman, a distraught Billie loses control, botches the deal, and ends up losing her job. Instead of returning home, she decides to stay in Rome – determined, for once, to simply enjoy life. Between aperitivos, reckless adventures, and a string of dates, Billie learns to live in the moment… until she discovers she’s pregnant. Not knowing who the father is, she hires private investigator Tommaso to help her solve the paternity mystery. As they navigate Rome together, their initial friction gives way to an unexpected attraction which turns into an emotional journey that forces both Billie and Tommaso to face their fears – and open up to the possibility of new love.