Episode 3 of "Cinderella at 2am" unfolds with a poignant flashback that unravels the tender beginnings of Joo-won's romance with Yoon-seo. Upon his return to Korea after two exhilarating years abroad, Joo-won confronts the harsh realities of internship life before ascending to a leadership position in his mother's esteemed company. Swiftly, he discovers that his self-perceived exceptionality fades against the backdrop of stern criticism from seniors and relentless pressure to indulge in excessive drinking during corporate gatherings.
Amidst his struggles, Yoon-seo's compassionate ears catch his despondent whispers of resignation to his brother. Alone, she offers a beacon of hope, urging him to forge ahead amidst the trials of being a novice. This fleeting moment ignites a spark within Joo-won, igniting his affection for Yoon-seo.
The narrative then glides to a poignant scene outside a restaurant, where a drunken Joo-won, overwhelmed by emotion, almost claims a kiss from Yoon-seo, only for her to subtly evade his advances. In a fit of frustration, he unleashes a storm of regrettable words, exposing Yoon-seo's intimate vulnerabilities. The aftermath leaves him wracked with guilt as dawn breaks.
The following day, the office air is thick with tension as Joo-won and Yoon-seo tiptoe around each other, their encounter the previous night casting a pall of awkwardness. Meanwhile, Yoon-seo's brother, Ji-suk, stands as a bystander to a bullying incident, choosing inaction despite his capacity to intervene, dismissing it as an inconvenience.
Fate, however, conspires to reunite Joo-won and Yoon-seo over lunch, where they tentatively agree to further discuss their complex emotions in Joo-won's office. But as fate would have it, Joo-won is summoned into an urgent call, leaving Yoon-seo to encounter the department chairwoman, who once again underscores her conviction that Yoon-seo must sever ties with Joo-won for the sake of his family.
With the chairwoman's words echoing in her mind, Yoon-seo seeks solace in I-rae's restaurant, laboring to banish thoughts of Joo-won. She pours her heart out to I-rae, confessing that her own lack of familial warmth has imbued her with a profound understanding of its value. Deeply aware of the bond between Joo-won and his family, she finds herself torn between her feelings and the desire to preserve his harmonious home.
The following day, Yoon-seo's world is jolted by a call from Ji-suk's teacher, summoning her to the forefront of the anti-bullying committee's attention. There, she is confronted with the unsettling truth that Ji-suk had stood as a passive witness to the torment of his classmate. Overcome with emotion, she offers a heartfelt apology to the aggrieved mother, shoulders the burden of not having adequately instilled a sense of righteousness in her son.
On the somber journey back home, Yoon-seo's voice trembles as she confronts Ji-suk about his choice to remain silent, the pain all the more poignant given her own harrowing past as a domestic abuse victim at the hands of their father. The memory of her ultimate escape, clutching Ji-suk close, only intensifies her disappointment in him for failing to speak out against injustice. Ji-suk, overwhelmed with guilt, acknowledges his lapse and vows to be more vocal in the future.
Meanwhile, Joo-won embarks on a journey of self-discovery as he visits his brother, realizing that his relentless pursuit of Yoon-seo was inadvertently weighing heavily on her shoulders. With a newfound clarity, he seeks out Yoon-seo and, amidst a poignant conversation, they mutually conclude that a parting of ways would be the kindest act. To mark the end of their relationship with a touch of nostalgia, they arrange for one last day filled with laughter and adventure at an amusement park, where they ride the thrills together, but ultimately, as the sun sets, they bid each other a bittersweet farewell.
