While You Were Sleeping

In the midst of a bustling Chicago winter, Lucy Eleanor Moderatz (Lucy) quietly collects fare tokens for the city's transit system at the Randolph/Wabash station. Unbeknownst to her coworkers, Lucy harbors a secret longing for Peter Callaghan, a handsome commuter who has captured her heart, despite their anonymity. On Christmas Day, fate intervenes when Lucy rescues Peter from the jaws of an oncoming train after muggers push him onto the tracks. As she accompanies Peter to the hospital, where he lies comatose, Lucy's musings aloud reveal her true feelings: "I was going to marry him." A nurse misinterprets her words as a declaration of engagement, and soon Peter's family is informed.

As Lucy becomes entangled in the crisis, she remains silent for several reasons. Embarrassment aside, she is worried about Peter's grandmother, Elsie, who suffers from a heart condition, and she finds herself swept up in the warmth of Peter's loving family. During her visits to Peter's bedside, Lucy confesses her predicament to him, unaware that his godfather, Saul, has overheard the truth. Saul, determined to keep Lucy's secret safe, reveals that she is alone, having lost both parents at a young age. He promises to maintain confidentiality, knowing that the accident has brought the family closer together.

Lucy becomes increasingly enamored with the quirky Callaghans and their unwavering love for her, unable to bring herself to hurt them by revealing Peter's ignorance. She spends a belated Christmas with them, then meets Peter's younger brother, Jack, who is poised to take over his father's furniture business. Initially skeptical of Lucy, Jack soon falls deeply in love with her as they bond over their shared sense of humor, travel aspirations, and intense affection for the Callaghans. As their relationship blossoms, Lucy finds herself torn between her love for Peter and her growing feelings for Jack.

However, their romance hits a snag when Jack, misinformed about Lucy's "pregnancy," announces it at her friend's New Year's Eve party. The ensuing argument reveals their mutual dissatisfaction with life. Meanwhile, Peter's actual girlfriend, Ashley, has been leaving messages on his answering machine, agreeing to marry him and expressing concern over his non-responsiveness. She returns to town, eager to reconnect with Peter and start a new chapter in their lives together.

As the calendar flips to a new year, Peter Callaghan awakens from a haze of uncertainty, his memories shrouded in mystery. His encounter with Lucy yields no recognition, prompting the assumption that he's suffering from amnesia. Meanwhile, Lucy's attempt to reveal the truth about her pregnancy is misinterpreted by the family, who assume she's denying the very notion of being pregnant. Enter Saul, a self-appointed mediator, who intercepts Lucy and vows to break the news to the Callaghan clan. Jack, ever the empathetic friend, takes Lucy under his wing, offering solace and support as she navigates the complexities of her situation.

In a moment of candor, Jack confesses his desire to abandon the family business and pursue his passion for furniture-making, met with his father's understanding and encouragement. This newfound sense of freedom allows Jack to open up about his true feelings for Lucy, who is touched by his kindness. As their bond deepens, Lucy finds herself torn between her affection for Peter and her growing connection with Jack.

Saul pays a visit to Peter, dispensing unsolicited advice on the importance of treating women with respect, cautioning that he would be fortunate to marry someone as special as Lucy. This timely intervention sets the stage for Peter's gradual transformation, as he begins to see Lucy in a new light. Meanwhile, Ashley Bartlett Bacon returns to the city, only to discover that her former beau is now engaged and recovering in the hospital. Confronting Peter about their past and his betrayal, she learns that he has since rejected her offer of marriage, unaware that she had accepted via answering machine.

As Lucy discovers that Saul never shared her revelation with the Callaghan family, she decides to take matters into her own hands, returning to the hospital to reveal the truth. In a poignant moment, Peter confesses his growing feelings for Lucy and proposes once more, only to be met with acceptance - though it's clear that her heart belongs to Jack.

On the eve of their wedding, Jack visits Lucy, offering her a chance to reevaluate her decision. With her emotions in turmoil, she asks if he can provide a reason to change her mind; his inability to do so leaves her feeling uncertain and disillusioned.

The day of the wedding arrives, only for Lucy to finally confess her true feelings to the family, revealing that she's fallen deeply in love with all of them - except Peter. As Ashley appears, demanding that the ceremony be halted, the family erupts into chaos. Amidst the commotion, Lucy slips away unnoticed, leaving her future hanging precariously in the balance.

As the days unfold, Jack seizes the perfect moment to make his move, depositing an engagement ring into the token tray of Lucy's booth, where it lies waiting like a promise. With the Callaghan family gathered around, he takes his place beside her and tenderly proposes, the air thick with anticipation. The couple exchanges vows, and their union is sealed before embarking on a romantic escapade aboard a CTA train, bound for Florence, Italy, the city of Lucy's dreams.

In a quiet reflection, Lucy reveals that it was during Peter's slumber that she fell deeply in love with Jack, her heart overflowing with emotion. The memory of that moment, suspended in time like a fleeting whisper, serves as the catalyst for their whirlwind romance, which culminates in a picturesque Italian getaway, replete with sun-kissed piazzas and cobblestone streets that whisper secrets to those who wander through its historic alleys.