You Are Here (1997)

Jack is a loyal corporate soldier who suddenly finds himself downsized along with the rest of the 24th floor. His boss takes pity on him and suggests he take the family estate, Glenmara, for the weekend to "clear his head and write a resume". Holly is told by a professional matchmaker that she is "too hesitant and over-cautious" and might be better off choosing a man at random. Jack asks the friendly stranger, Holly to Glenmara for the weekend. Holly, at the end of her romantic rope, says yes. What seems at first to be a serendipitous beginning for an awkward young couple turns through misfortune, mishap and histories of romantic wreckage into a screwball journey.