Mary Horowitz, an eccentric and socially awkward crossword puzzle creator, is set up on a blind date with Steve, a handsome and charming CNN cameraman. Immediately smitten, Mary talks incessantly throughout the date, which overwhelms Steve. Despite his polite rejection, Mary becomes convinced that Steve is her destiny and embarks on a cross-country adventure to pursue him. Her obsessive behavior leads her to follow Steve from assignment to assignment, believing that their paths are meant to cross repeatedly.

Unbeknownst to Steve, Mary's antics quickly gain the attention of the media, spurred on by Hartman Hughes, a manipulative news reporter who sees the potential for a quirky human interest story. This results in a series of comedic and awkward encounters as Mary’s determination brings her into various unpredictable situations. Along the journey, Mary learns more about herself, her obsessions, and what it truly means to pursue one's aspirations.