Classic Romantic Moment of the Month: Fall In Love With While You Were Sleeping

THE MOVIE: While You Were Sleeping (1995)

THE PAIRING: Lucy (Sandra Bullock) and Jack (Bill Pullman)

THE SCENE: Jack gives Lucy a ride home after a family event.

There’s something about the romantic comedies from the 90s. They possess a kind of joyful quality that is sometimes missing from today’s box office. One of these films is While You Were Sleeping, a movie full of romantic moments.

THE STORY: WHILE YOU WERE SLEEPING

In case you haven’t seen While You Were Sleeping or it’s been a while, the story goes something like this:

Lucy crushes on the handsome Peter, a man she sees every day while at work. However, the two have never met. Still, she imagines him as a prince charming. One day, she saves him when he’s pushed onto the tracks with an oncoming train, and through a series of events, his family believes Lucy is Peter’s fiancé. Unfortunately for Lucy, Peter cannot set his family to rights given he’s in a coma.

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So, for the holidays, Lucy plays fiancé to a man she doesn’t know, all while falling in love with a man she most definitely is not engaged to, his brother. For a lonely woman with nowhere to go on Christmas, she can finally feel like she has a family.

There is so much to love about this film, not the least of which is the romance, which we spotlight today.

THE LEAD IN: WHILE YOU WERE SLEEPING

Throughout her entrance into this crazy albeit lovable family, Lucy struggles with the fact that she’s lying to them. They’re good people, and she doesn’t quite know how to tell them the truth. Things grow more strained when she meets Jack. He’s unlike Peter, but nonetheless, she’s drawn to him.

During the story, Peter’s family continues to include Lucy in all of their family traditions, but it’s Jack with whom she finds herself most at ease with. They get to know one another in unexpected ways through an unexpected friendship. Lucy comes to learn about his dreams and she looks forward to their conversations. Discussions that often lead to some flirty banter, and ends for her with a smile. It’s during these conversations that Lucy slowly, but wholeheartedly falls head over heels in love with Jack.

Whether he’s walking her home, and they share a close encounter as he walks her to her door; or he surprises her with a snow globe of Italy (a dream vacation she someday hopes to see), they grow close. In fact, right before her wedding, as he walks away from her door with a heart that is breaking, she follows him out and asks the most important question of her life.

With an expression of hopeful sincerity, she asks him, “Can you give me any reason… why l shouldn’t marry your brother?”

As if it pains him, on an exhale he replies with longing on his face, he tells her, “I can’t.”

She gently nods and lets him walk out the door. Because she worries over the effect it will have on his family, Lucy plans to go through with her marriage to Peter until she can’t… even without a reason not to.

THE ROMANTIC MOMENT: WHILE YOU WERE SLEEPING

No matter her good intentions, Lucy finds when the day arrives, she cannot marry Peter. He’s good and kind, but it’s not he who holds her heart. Instead, she confesses to him and his family (including Jack!) who her heart belongs to.

Embarrassed and not expecting to see this family ever again, she walks out of the wedding, and returns to her simple life and job; which she is about to leave in pursuit of travel.

As she finishes her shift, the most unexpected token falls into her booth – a diamond ring!

She picks it up and looks up to see Jack, and his family, smiling anxiously.

“Lucy,” he begins, “I need to ask you a question.”

As they lock gazes, in the background, his family offers advice on how best to propose.

Trying to ignore them, Jack softly queries, “Can I come in there, please?”

Putting on a somber face, she tells him, “I can’t.” For a moment it looks as though she’s about to break his heart. Then, she says, “Not without a token.” Dropping one in, he walks around where she opens the booth door for him.

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Together, at last, Jack leans into Lucy. With a question meant only for her, he quietly asks, “Marry me?”

Simply, she replies, “Yeah.” Remaining close, she tells him, “I love you.”

Confident he is now free to do so, he replies, “I love you back.”

The two come together to seal their promise with a kiss. Their love story one that is only beginning; a story that, as she tells Peter, could only begin “while you were sleeping.”

You can rent or own While You Were Sleeping on DVD or on Amazon Video. PS: it’s worth seeing at least once.

What are your thoughts on this classic (I’m calling it so in my romcom book!) that USA Today called “irresistible”? Is it an old favorite? What are your thoughts on this moment or this couple? I’d love to chat with you about Jack, Lucy, and their unexpected romance. Leave all the thoughts on our ‘Romantic Moment: While You Were Sleeping’ down below. 

Photos: Hollywood Pictures and Caravan Pictures / Buena Vista Pictures

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