While You Were Sleeping captures a 1990s Chicago defined by CTA tokens and neighborhood intimacy, following a token collector whose impulsive act of heroism entangles her in a lie—and a romance with the man’s brother.

Lucy Eleanor Moderatz (Sandra Bullock) works as a fare token collector at the Randolph/Wabash station in Chicago, secretly infatuated with regular commuter Peter Callaghan (Peter Gallagher). On Xmas Day, she rescues him after muggers push him onto the train tracks. At the hospital, Peter’s family mistakes Lucy for his fiancée. Grateful yet surprised, they welcome her warmly. Embarrassed and afraid of upsetting Peter’s grandmother Elsie (Glynis Johns), Lucy stays silent about the misunderstanding. She confesses her predicament to comatose Peter, unaware his godfather Saul Tuttle (Jack Warden) overhears, while Peter’s girlfriend Ashley (Ally Walker) leaves messages deciding to accept his proposal.

Drawn to the quirky and loving Callaghans, Lucy reluctantly joins their Xmas celebrations. She meets Peter’s brother Jack (Bill Pullman), who wishes to pursue his own furniture business rather than inherit the family estate. Initially suspicious of Lucy, Jack comes to trust her. Meanwhile, Saul quietly monitors the situation and later visits Lucy, who explains her loneliness after losing her parents. Understanding, he keeps her secret, knowing her intentions aren’t malicious. As Lucy and Jack grow closer, romantic tension develops, complicated by misunderstandings, including Jack believing Lucy might be pregnant.

After Peter awakens, amnesia is assumed, allowing Lucy’s secret to linger. Miscommunications continue as Ashley returns to assert her engagement, while Saul encourages Peter to appreciate Lucy. Peter’s charm and change of heart make him realize her specialness. Lucy tries to reveal the truth but is interrupted by the family assuming she speaks of the nonexistent pregnancy. Jack and Lucy share moments of friendship and reflection, while Peter prepares to marry Lucy. Lucy grapples with her feelings as Jack subtly expresses his own, setting up the emotional climax.

At the wedding, Lucy objects, confessing her love for Jack and revealing her full truth to the family. Amid chaos—including Ashley and her husband arriving—Lucy slips away. Later, Jack proposes to her in her token booth, witnessed by the Callaghans. Lucy accepts, and they marry, taking a CTA train for their honeymoon to Florence, Italy. When Peter asks when she fell for Jack, Lucy smiles, “It was while you were sleeping.”

When While You Were Sleeping was released in 1995, it joined a crowd of rom-coms that included When Harry Met Sally…, Pretty Woman, and Sleepless in Seattle. It would be another three years—and then some—before Tom Hanks and Meg Ryan’s hit reunion in You’ve Got Mail. The 1990s and 2000s were a special time, as studios could rely on rom-coms in a way they don’t really do as much these days—at least, it doesn’t feel that way. The film would earn Sandra Bullock her first Golden Globe nomination years before the organization took a serious hit to its credibility. Interestingly enough, Meg Ryan passed on the film prior to the script being reworked.

While You Were Sleeping lives and dies on buying into Sandra Bullock as a token collector. Never mind the other issues with the film—if you cannot buy into the idea of Bullock working in the CTA booth, it might pose a problem. But for some reason, it’s easier picturing her than some of the other actresses considered for the film, like Demi Moore, Nicole Kidman, Julia Roberts, or Meg Ryan. Geena Davis had even been considered up until Jon Turteltaub’s hiring. As for the male love interest, it’s far easier buying into Bill Pullman than Matthew McConaughey.

What sets While You Were Sleeping apart from other films is that it’s not trying to be a fairy tale comedy. There’s no dramatic transformation for Lucy. And even if there were, it’s a Chicago winter, so she’s dressing appropriately for the season. But anyway, Lucy isn’t after all the fancy gifts—what she wants is a family, and she manages to find one in the Callaghans.

While there is plenty of absurdity throughout While You Were Sleeping, I can’t go without commenting on the Chicago of it all. By the time I relocated to Chicago for the first time in 2008, CTA tokens were a thing of the past. Things have changed since then, with the CTA now relying on Ventra. As such, the film is more or less a time capsule, capturing a CTA stop that no longer exists. The Randolph/Wabash stop closed in 2017 when its replacement at Washington/Wabash opened.

There are some things that need to be discussed about the CTA issues in While You Were Sleeping. It’s highly unlikely that Lucy would have rushed to the tracks in real life. Instead, she would have immediately called medical professionals, the tracks would have been shut down, and the oncoming Orange Line train would have halted its route until Peter was removed from the tracks. I’ve lived in Chicago long enough to know that this part of the film is unrealistic. Speaking of the Orange Line, if Peter lives on the North Side, why is he riding a train that’s headed south? MAKE IT MAKE SENSE!

You know what else isn’t realistic? Lucy waiting until the end of While You Were Sleeping to finally tell the truth. I get it—she’s lonely and wants to spend time with a family, especially Peter’s, after being infatuated with him from inside the CTA booth. But she should have opened up about the truth from the get-go, rather than letting the lie become the truth at the hospital.

The original setting for While You Were Sleeping had been New York City. It was smart of the filmmakers to change the location to Chicago and then film the rom-com on location rather than just using the city for exterior shots. I understand why filmmakers love to shoot in New York, but it’s nice to see them share the love for other cities every once in a while. While the film gets some logistical details wrong about how the CTA would respond to a medical emergency, they didn’t pull a move like Never Been Kissed and film exterior scenes in Los Angeles with mountains in the background.

Despite the flaws in While You Were Sleeping, the film was a box office smash, earning $182 million against a $17 million budget in 1995. Can you imagine rom-coms making this much in 2026? It feels like studios just don’t take chances on them like they used to. Not to mention the fact that the film came from Disney’s Hollywood Pictures and Caravan Pictures, when Disney was distributing films under Buena Vista Pictures Distribution, Inc. Hollywood Pictures’ films featured mature themes and were targeted to adult audiences, similar to another Disney label, Touchstone Pictures.

Despite its flaws, While You Were Sleeping endures as a rom-com that thrives on its casting and its Chicago setting, even if it asks viewers to accept some significant leaps in logic along the way. Sandra Bullock anchors the film with an affability that makes Lucy believable in a role that could have easily faltered, and Bill Pullman offers a grounded counterpart that helps the central romance take shape. Still, the film’s realism issues and Lucy’s delayed truth-telling keep it from fully landing emotionally. What remains is a charming, occasionally frustrating 1990s rom-com that captures both a specific place and a specific era—one that works, even if it doesn’t entirely win you over.

DIRECTOR: Jon Turteltaub
SCREENWRITERS: Daniel G. Sullivan & Fredric Lebow
CAST: Sandra Bullock, Bill Pullman, Peter Gallagher, Peter Boyle, Glynis Johns, Micole Mercurio, and Jack Warden, Jason Bernard, Michael Rispoli, Ally Walker, Monica Keena

Hollywood Pictures released While You Were Sleeping in theaters on April 21, 1995: Grade: 3.5/5

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