When a non-confrontational playwright loses her engagement ring, she must travel through Italy to get it back with a man who was supposed to be just a one-night stand, discussing love and lying along the way. Eleanor (Cooke), an English playwright engaged to Noah, travels to Rome for an acting role research. There, she encounters a witty tour guide, Lucas (Bell), and they share a memorable night. However, Eleanor loses her engagement ring, leading her back to Rome with Lucas' help to find it. As they spend more time together, they both reveal their cheating tendencies. They bond over their flaws, making them oddly endearing. Despite being scolded by her lesbian friend for being straight, Eleanor breaks off her engagement with Noah. The question remains whether she will give Lucas another chance, adding an element of uncertainty to her romantic journey