Episode 2 of "Cinderella at 2am" delves deeper into the intricate web of emotions as Yoon-seo's world is turned upside down upon discovering that her ex-boyfriend, Joo-won, has not embarked on a foreign sojourn but rather been reinstated as the company's director. The dramatic turn of events takes a surreal twist when Joo-won himself appears, heroically averting Yoon-seo's fall down the staircase.
A poignant flashback transports us to the moment when Joo-won's subtle confession first captivated Yoon-seo's heart, leaving her enchanted. To her astonishment, Joo-won's office now adjoins her team's workspace, granting him a constant, unobstructed view of her. This revelation stuns Yoon-seo's colleagues, who are further shocked to learn that their youngest team member harbors a hidden identity as the chairwoman's son.
Yoon-seo confronts Joo-won in his office, seeking clarity amidst the chaos. Joo-won, however, remains steadfast in his commitment to fulfill his promise of relentless pursuit, mischievously revealing that he's been taking cues from the internet on how to showcase a new facet of himself to win her back. His playful demeanor is evident as he affectionately strokes her hair, inadvertently triggering the transparent screen button, exposing their intimate moment to the amused yet oblivious gazes of their teammates.
With Joo-won's return, his intentions are clear: to infiltrate every aspect of Yoon-seo's life, from sharing meals with her team to boldly declaring his intention to rekindle their romance. Yet, Yoon-seo stands firm in her resolve to sever their past ties.
Meanwhile, a comedic interlude introduces Si-wan, Joo-won's older brother, lounging in his underwear at home, reveling in the unfettered freedom he's embraced since his wife's relocation abroad. This absurd scene serves as a humorous respite, contrasting the intensity of Yoon-seo and Joo-won's drama. Through their brotherly banter, we gain insight into the depths of Joo-won's feelings for Yoon-seo; he, who once shunned movies, has now transformed into a cinephile solely because of her.
As Yoon-seo journeys home from I-rae's restaurant, a heartbreaking revelation unfolds—she has been a victim of abuse at the hands of her alcoholic father, casting a somber shadow over the complexities of her relationship with Joo-won.
The following day, amidst a pressing project's demands, Yoon-seo, despite feeling unwell, perseveres and heads to the office. In the elevator, her path crosses with Si-wan, who shares a candid insight into Joo-won's stubborn nature. Intriguingly, he divulges that Joo-won, once averse to movies, has transformed into a cinephile since meeting Yoon-seo. This revelation stirs memories of their shared movie nights, causing Yoon-seo to reflect. As she engages with Si-wan, she realizes her unwitting oversight; Joo-won's enthusiasm for opera went unacknowledged, his invitation unfulfilled, leaving her with a pang of guilt.
Later, under the cloak of night, Joo-won's attentive nature shines through as he delivers porridge and medicine to Yoon-seo, noticing her fitful coughing. However, fate intervenes as Yoon-seo faints mid-journey, prompting Joo-won to swiftly escort her to the hospital. Upon regaining consciousness, Yoon-seo confronts Joo-won about his film fascination, and he confesses that accompanying her was a means to cherish her smile, a journey that unexpectedly led him to embrace films. Amidst this honesty, they devise a quirky plan: sharing 27 meals together as an attempt, albeit ironic, to end their relationship—a challenge Joo-won approaches with unwavering confidence in reconciling their bond.
Their meals together blossom into cherished reunions, echoing their past joys. Each gathering sees Yoon-seo lowering her defenses, yet steadfastly maintaining, "We broke up," whenever their status is queried. Joo-won's mother, privy to their rendezvous, confides in Si-wan, expressing faith in Yoon-seo's commitment to her word.
Over drinks during one of their dinner rendezvous, Yoon-seo's defenses finally crumble under Joo-won's gentle inquiry about her feelings. "I still like you a lot," she admits, her words ringing with sincerity. As the episode draws to a close, Joo-won leans in, closing the distance between them, poised for a kiss that encapsulates their rekindled connection.
