Episode 5 of "Cinderella at 2 AM" gracefully unfolds with a poignant flashback, painting a vivid picture of how Yoon-seo's team, accompanied by I-rae, stumbled upon her humble abode. Following a hearty lunch, Yoon-seo's junior colleagues opt to gather for dinner at her place, hoping to leverage the assistant manager's assistance in tutoring her brother through his math homework. Little did they know, this impromptu dinner would serve as the stage for a surprise revelation.
As I-rae sets out to deliver the culinary treats, Ju-won's unexpected arrival and tender embrace towards Yoon-seo unmask their once-hidden romantic entanglement to their startled colleagues. Their mutual disclosure that the relationship had dissolved a month prior only serves to ignite a whirlwind of curiosity and wild speculations within the team, spinning intricate theories around the enigmatic split.
Yoon-seo finds herself besieged by a barrage of inquisitive glances and probing questions from her nosy peers, creating an uneasy ambiance within the office walls. Amidst this comedic chaos, fate deals her a series of humorous mishaps: a chance encounter with the janitor results in an accidental slap, which her colleagues erroneously attribute to Ju-won's overbearing mother. Moreover, a blundered blind date with a headhunter, mistaken for a professional meeting, adds another layer of comedic embarrassment to her already tumultuous day. To her dismay, Ju-won's eavesdropping on her date only compounds the complexity of her situation.
Elsewhere, Ju-won's mother's anxiety over his departure from home prompts Si-won's visit, where he pleads with Ju-won to reconsider his decision. In a heartfelt confession, Ju-won reveals that Yoon-seo holds a special place in his heart as the first person he conquered on his own, professing his undying devotion and vowing to remain pining for her.
Wearied by the relentless office gossip and dramas, Yoon-seo decides to take a respite from her hectic life, sneaking out of work early. Her journey home, however, is marred by a heated confrontation with a reckless driver. To top it all off, a call from the enigmatic suitor who has been relentlessly pursuing her adds fuel to her frayed nerves. In a moment of utter frustration, she silences her phone, escaping into the solace of the Han River, seeking refuge from the chaos that surrounds her.
Back at the office, a tempest of scandal engulfs the team, centered around their artist, leaving them in a quagmire as they struggle to reach Yoon-seo. Amidst the turmoil, Ju-won emerges as a beacon of resolve, proposing they reconnect with Lee Seong-min, the original artist they had their hearts set on collaborating with. With steely determination, he vows to make this partnership a reality.
Elsewhere, Si-won extends an invitation to Mi-jin for dinner, which she gracefully accepts, only to mischievously reveal the venue as a gathering with her friends. Disappointed, Si-won departs, but their subsequent conversation about their communication shortcomings sparks a turning point. Mi-jin pledges to maintain contact and confesses that her marriage to Si-won wasn't merely an arrangement; she genuinely harbored feelings for him, a revelation that breathes new life into their relationship.
Meanwhile, the team triumphantly secures Lee Seong-min's agreement to collaborate, fueling a marathon session that stretches deep into the night. Just as hope seemed to wane, Yoon-seo arrives, phone reactivated, to lend a helping hand. She offers apologies to the team, yet Ju-won remains distant, his heart still smarting from her blind date escapade.
The following dawn brings a surprising revelation for Yoon-seo: the enigmatic figure who had been incessantly calling and messaging her is none other than the charismatic artist, Seong-min. Ju-won, too, catches on, sensing a potential romantic interest brewing between Seong-min and Yoon-seo. As the episode draws to a close, the two men engage in a subtle yet intense competition, each vying for the opportunity to share breakfast with Yoon-seo, setting the stage for an intriguing triangle of emotions.
