Episode 1 of "Cinderella at 2am" kicks off with a heart-racing confrontation, as our protagonist, Ha Yoon-seo, finds herself face-to-face with her boyfriend's formidable mother, the very chairperson of her employer. In this charged atmosphere, Yoon-seo reluctantly agrees to sever ties with Joo-won, even accepting financial compensation to ease the inevitable pain. She vows to carry out this difficult task within two months, her heart heavy with the thought of sparing Joo-won as much heartbreak as possible.
It swiftly becomes apparent that beneath the veneer of their cherished bond, Yoon-seo senses a chasm separating their worlds. Confiding in her friend, Kim I-rae, she laments how Joo-won's gift of an extravagant bag on their anniversary stands as a stark reminder of their disparate lifestyles.
Flashing back, we witness Yoon-seo's comical yet poignant reaction upon overhearing Joo-won's revelation to his brother, the Vice Chairperson Si-won, about his privileged background. Her initial jest, "You're from a rich family? Why keep me in the dark? And let me foot the bill all this while?" belies the complexity of her emotions.
As Yoon-seo's scheme to end the relationship unfolds, Joo-won's impending overseas transfer looms large. Yet, Joo-won, ever-perceptive, senses a shift in Yoon-seo's demeanor and seeks counsel from Si-won, who flippantly dismisses his concerns, inadvertently revealing the shallowness of his own arranged marriage, monitored solely through Instagram updates.
Determined to drive Joo-won away, Yoon-seo embarks on a desperate quest to become the epitome of irritability and inconvenience. But her efforts prove futile; Joo-won's affection for her remains steadfast. In a moment of desperation, she seeks solace in alcohol with I-rae, only to stumble into a near-disasterous drunken text to Joo-won.
The morning after brings a shocking realization: Yoon-seo has inadvertently broadcasted a half-baked breakup message to her work group chat. Amidst the chaos, she struggles to recall a hazy 10-second conversation with Joo-won, her mind a blur. Crafting a tenuous explanation for her drunken misstep, she's met with Joo-won's casual dismissal, as he mischievously suggests she merely called to bid him goodnight. The stage is thus set for a tumultuous journey, where love, secrets, and societal expectations intertwine in a tale of resilience and self-discovery.
After a long day at work, Yoon-seo stumbles across a haunting recording of a fleeting, ten-second phone call—a moment where, unknowingly, she had uttered the fateful words to Joo-won, initiating their breakup. Confronted with the truth, he reveals a stunning revelation: he was aware of her secret meeting with his mother yet remained steadfast in his desire to be by her side. But Yoon-seo, resolute in her convictions, underscores the irreconcilable gaps in their backgrounds and lifestyles, ultimately severing their ties with a heartrending finality.
Time elapses, painting a picture of Joo-won's overseas transfer and Yoon-seo's relentless pursuit of her career. Yet, fate干预s in the most unexpected manner when Joo-won reenters her life, now adorned with the title of company director. Their paths cross once more beneath the iconic, Cinderella-inspired staircase, where he bends down gracefully to assist her with her shoe, his eyes ablaze with determination. In a bold move, he proclaims his unwavering intention to pursue her relentlessly, his every action a testament to his undying devotion and clinginess.
