Never Been Kissed (1999) Characters, Setting & Themes Explained

The movie is set primarily in Chicago, where Josie Geller works as a junior copywriter at the Chicago Sun-Times. The main setting for her undercover story is South Glen South High School, the fictional high school where she goes undercover as a student to investigate teenage trends.

• chicago
• south glen south high school
• setting
• location

Never Been Kissed is set in the late 1990s, capturing the cultural and social atmosphere of that era. The film reflects the period's communication styles and social pressures as technology was beginning to influence how young people interacted.

• 1990s
• late 1990s
• time period
• era

Josie Geller is the protagonist, a junior copywriter at the Chicago Sun-Times who is assigned to go undercover at her old high school for a story. She is portrayed as intelligent but socially awkward, carrying insecurities from her difficult high school experience.

• josie geller
• protagonist
• main character
• heroine

Josie Geller works as a junior copywriter at the Chicago Sun-Times, a major newspaper in Chicago. Her assignment to go undercover at South Glen South High School is given to her by her boss Gus as an opportunity to prove herself at the newspaper.

• copywriter
• chicago sun-times
• journalist
• newspaper job

Sam Coulson is Josie's attractive English teacher at South Glen South High School. He is described as an inspiring teacher who shares Josie's passion for literature. He serves as a beacon of hope and encouragement, helping to ignite Josie's confidence and self-worth during her undercover assignment.

• sam coulson
• english teacher
• love interest
• mentor

The theme of acceptance is central to Josie's journey. She must confront her painful high school past and learn to be true to herself despite societal pressures to conform and fit in. Her experiences at South Glen South High force her to face old insecurities and ultimately find self-acceptance.

• acceptance
• self-acceptance
• authenticity
• fitting in

Identity is a major theme as Josie struggles to reinvent herself and find her place among her peers. The movie explores the struggles of self-discovery and how past experiences impact one's self-esteem and social acceptance. Josie's undercover mission forces her to confront who she was versus who she wants to become.

• identity
• self-discovery
• reinvention
• personal growth

Romance emerges as Josie develops feelings for her English teacher Sam Coulson while undercover. The narrative also includes her confronting a past high school crush, adding emotional layers to her story. The romance explores the ups and downs of infatuation, particularly in the context of adolescence and the complications of her secret identity.

• romance
• love interest
• teacher student relationship
• crush

The title Never Been Kissed refers to Josie's personal history - as an adult, she reveals she has never been kissed, which stems from her traumatic high school experience of being mocked and humiliated. This becomes a central element of her emotional journey toward self-acceptance and eventually finding love.

• title meaning
• never been kissed
• first kiss
• virginity

Gus is Josie's boss at the Chicago Sun-Times. He is skeptical of Josie's reporting abilities and assigns her the high school undercover story, doubting she can pull it off. His initial doubt represents the professional challenges Josie faces, though he eventually recognizes her potential.

• gus
• boss
• chicago sun-times
• editor

South Glen South High School serves as the primary setting where Josie goes undercover as a student. The school environment encapsulates the social dynamics of teenage life, including the excitement and challenges students face. For Josie, returning to this setting forces her to relive painful memories while also providing an opportunity for personal growth and redemption.

• high school
• south glen south
• teenage social dynamics
• undercover