Never Been Kissed, a Chicago-set romantic comedy starring Drew Barrymore, marks its 27th anniversary since the film’s theatrical release in 1999.

Josie Geller (Drew Barrymore) is a shy, 25-year-old copy editor at the Chicago Sun-Times who has never experienced a serious relationship. Hoping to boost readership, her editor-in-chief, James Rigfort (Garry Marshall), assigns her to go undercover as a high school student and report on teenage life. Posing as a senior at South Glen South High School, Josie quickly finds herself reliving the insecurities that defined her first time through adolescence.

Her return to high school proves painful. Josie slips back into her awkward “geek” persona and clashes with popular girls Kirsten (Jessica Alba), Gibby (Jordan Ladd), and Kristin (Marley Shelton), along with charismatic heartthrob Guy Perkins (Jeremy Jordan). She finds comfort in befriending Aldys (Leelee Sobieski), a sharp and independent student who invites her into an academic clique. Meanwhile, Josie develops feelings for her English teacher, Sam Coulson (Michael Vartan), triggering memories of a humiliating prom-night betrayal by her former crush, Billy Prince (Denny Kirkwood).

Pressured by managing editor Augustus “Gus” Strauss (John C. Reilly) after a rival paper beats them to a story, Josie is urged to get closer to the popular crowd and wears a hidden camera to capture material. With encouragement from her brother Rob (David Arquette), a former high school star who enrolls to help her navigate the social scene, Josie rises in popularity. However, her growing closeness to Sam and her shifting loyalties strain her friendship with Aldys and complicate her secret.

At prom, Josie is crowned queen but rejects the cruelty of her classmates, publicly revealing her true identity and defending Aldys. The fallout costs her both Sam’s trust and Rob’s second chance at glory, though she later helps secure him a coaching job. Josie writes a heartfelt front-page confession about her experience and declares her love for Sam, promising to wait for him on the baseball field. After a tense delay, Sam arrives, and the two finally share a long-awaited kiss.

When I rewatched Never Been Kissed in March, it was the first rewatch since the theatrical release or sometime thereafter. I didn’t exactly log video rentals or when I watched films on cable, so it’s hard to account for some of those early-2000s repeat viewings. One thing I didn’t think about until this particular viewing was how Mean Girls shares DNA with the 1999 romantic comedy.

Both films focus on social hierarchies in high school, with a particular lens on the outsiders and the popular crowd. We experience Never Been Kissed through Josie’s outsider perspective, while audiences watch Mean Girls through Cady’s lens. The awkwardness and misfit status lend the film a dose of empathy and humor. But in both films, the protagonist manages to reinvent themselves and join the popular crowd during a transformation arc, only to end up learning a lesson about authenticity in the process. Similarly, they both use humor as a lens for highlighting the absurd social rules or adolescent cruelty, but to my knowledge, this film has never been viewed as a satire.

At 25 years old, Josie has been through high school already, but it wasn’t the best experience, as flashbacks make known. That’s what makes it so different this time when she enrolls. She’s working undercover but reverts back to the geek persona. When her brother enters the picture, it’s a whole new ballgame. The hot guy in school becomes interested in her, but joining the in crowd is a betrayal to new friends like Aldys. It would have been nice to see her writing more stories based on her undercover experience, but she only turns in an article that moves the whole city by detailing her experiences. It’s not the exposé that one might expect.

I don’t think a newspaper would actually employ a hidden camera on one of their reporters, especially in 1999. This feels more like spy stuff than anything else. You just have to laugh at the preposterousness of it all! On one hand, it enables Never Been Kissed to show some diversity because Cress Williams and Octavia Spencer are among the very few Black people with speaking roles.

For all the parts that make Never Been Kissed charming, there are other aspects that do not age well when watching through a 2026 lens. Sam Coulson is a teacher and grows close with Josie, who is 25 years old but pretending to be a high school senior. Talk about power dynamics! On the other end of the coin is Rob, who goes to prom with Tracy. You couldn’t get away with that today. Meanwhile, Drew Barrymore is only two years younger than Jeremy Jordan in real life, but she’s supposed to be older than him in the film!

Some of Never Been Kissed was shot in Los Angeles, and this is especially noticeable in the schools and athletic venues being used as filming locations. There are no mountains in Chicago. It would have been nice for some authenticity here, but I understand why filmmakers would have preferred to film in the LA vicinity. It’s easier for actors and crew to stay closer to home than spend more on the budget by filming elsewhere. But if that’s the case, why not have Josie working for the Los Angeles Times or another LA newspaper?

Living in Chicago means watching closely for any Chicago shots. The Chicago Sun-Times building along Wabash Avenue, just north of the Chicago River, hasn’t been there since being demolished in 2004. I’d have to rewatch Batman Begins to see if there are any shots of the building there, but chances are likely that Never Been Kissed is among the final films that featured its exterior. Interestingly, Josie’s home is located within the Lakeview neighborhood, not too far from John Candy’s home in Only the Lonely. There are other places, too, such as the Chicago and Franklin stop along the Brown Line.

The use of The Beach Boys’ “Don’t Worry Baby” during the final moments couldn’t have been more appropriate. In a way, it’s the musical way of Sam telling Josie that everything will be all right. Sure, he was late, but they get their happy ending.

Overall, Never Been Kissed is a charming and engaging romantic comedy that holds up in a number of places all these years later, though a few implausible plot points and dated social dynamics keep it from being anywhere close to perfect.

DIRECTOR: Raja Gosnell
SCREENWRITERS Abby Kohn & Mark Silverstein
CAST: Drew Barrymore, David Arquette, Michael Vartan, Leelee Sobieski, Jeremy Jordan, Molly Shannon, Garry Marshall, Marley Shelton, Jessica Alba, Jordan Ladd, Branden Williams, Sean Whalen, Cress Williams, Gregory Sporleder, and John C. Reilly

20th Century Fox released Never Been Kissed in theaters on April 9, 1999. Grade: 3.5/5

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