If you’ve ever wondered what would happen if a K-drama Cinderella went against the trope and accepted the proffered envelope of money from her prince’s disapproving mother, then this is the drama for you. However, just because our leading lady readily accepts the cash, that doesn’t guarantee ending her relationship will be easy.
EPISODES 1-2
Our modern fairy tale begins in media res with a scene that’s as familiar to K-drama veterans as wrist grabs, product placements, and white Trucks of Doom. HA YOON-SEO (Shin Hyun-bin) is seated at a private dining table across from KIM SUN-JOO (Jin Hee-kyung), the elegant — and immensely rich — chairwoman of AL Group, Yoon-seo’s employer. More importantly, though, Chairwoman Kim is the mother of Yoon-seo’s undercover chaebol boyfriend SEO JOO-WON (Moon Sang-min).
Like many disapproving chaebol mommas before her, Sun-joo tells Yoon-seo to break up with her son in exchange for a large sum of money — to be wired to her bank account, of course, because envelopes full of cash are so circa Boys Before Flowers. However, there’s a plot twist to this particular story: instead of rejecting the money like so many Candies and Cinderellas before her, Yoon-seo writes down her bank account information and agrees to break up with Joo-won — but not immediately.
If she breaks up with Joo-won now — abruptly and not too long after accidentally learning of his chaebol status — then he would figure out that his mother instigated their breakup, and if Yoon-seo is going to be the gold-digging girlfriend who takes the money, then she’d rather not drive a wedge between Joo-won and his mother in the process. Instead, Yoon-seo plans to slowly break up with Joo-won over the course of the next two months, hoping she can create enough animosity between them that will make their breakup feel more organic so that he won’t question her motives. Or, even better, maybe she can push him to the point of breaking up with her. In return, Charwoman Kim promises to transfer Joo-won to an overseas division of AL Group after the breakup.
However, Yoon-seo quickly learns that one does not simply break up with one’s boyfriend — especially not when he’s extremely thoughtful and attuned to her personality quirks. Drawing inspiration from the internet, Yoon-seo does her best to Kate Hudson her way through losing a guy in ten days two months, but her juvenile methods of pushing Joo-won away are more baffling than off-putting. She might try to play the role of an indecisive and stubborn girlfriend who can’t decide where she wants to eat, but Joo-won, who knows her extremely well, expertly navigates her false hangryness and takes her to one of her favorite restaurants to fix his malfunctioning girlfriend.
The familiarity of the comfort food and Joo-won’s charming presence cause Yoon-seo to forget her objective, and she easily slips back in sync with Joo-won, making her realize that it will be harder for her to break up with him than she’d previously thought. From the moment she found out he was a chaebol, she pragmatically assumed that a breakup would be inevitable because of the massive gap in their socioeconomic statuses. After all, there’s no such thing as a Cinderella romance in real life — which is why she rationalized that it was better to at least get some money out of Joo-won’s mother while she could — but that doesn’t negate the fact that she cares about Joo-won and doesn’t want to hurt him.
The inner turmoil drives Yoon-seo to drink herself silly, a move she regrets the next day when she realizes she drunk texted a partial break-up message to her work group chat and, according to her call history, had a phone conversation with Joo-won that she can’t remember. Thankfully, the other members of Yoon-seo’s team, BAE JANG-HEE (Lee Kyu-sung) and NOH YE-YOUNG (Kim Gyu-nam) are comically oblivious and misinterpret text, but what about her phone call with Joo-won?
Well, he claims he called her to see if she was all right after seeing the text, but after finding a recording on her phone of her drinking call with Joo-won, Yoon-seo realizes that she’d actually broken up with him. Joo-won tells her he pretended it didn’t happen because he didn’t want it to be real, but now that the secret is out of the bag, Yoon-seo pushes forward with the breakup. Joo-won tries to fight it, revealing that his older brother SEO SHI-WON (Yoon Park) told him that their mother had asked Yoon-seo to break up with him, but even with the whole truth out in the open, Yoon-seo won’t be swayed. She already took the money, and she firmly believes that, one way or another, their different social classes will doom them.
A week passes, and Yoon-seo, who can’t afford to lose focus because of a breakup, throws herself into her job while Jang-hee and Ye-young complain that Joo-won, their hoobae whose chaebol status is still unknown to them, took an unexpected vacation. Presumably, his mother made good on her promise to send him overseas, but it turns out that is very much not the case because, a week after their breakup, Joo-won returns to AL Group as the outed second son of Chairwoman Kim.
He’s not only been given a promotion that suits his status as a chaebol, but he gives back to his former teammates — now subordinates — by stocking the break rooms with premium snacks and massage chairs. His dramatic return to the company is a major shock for Yoon-seo, and when she reads the notice of his appointment as director, she stumbles, slips out of shoe, and nearly falls down an elegant grand staircase that looks totally incongruous with the office setting. As if the allusions to Cinderella weren’t obvious enough, Joo-won races up the stairs, and after dramatically catching Yoon-seo in his arms, he shifts her to a standing position so he can bend down and slip her shoe back onto her foot.
In addition to being a nod to Cinderella’s glass slipper, Joo-won’s sensational return is a callback to the beginning of his courtship of Yoon-seo a year and a half ago. After a team dinner, Yoon-seo’s shoe had malfunctioned and Joo-won had raced to a nearby stationery store to buy her some cartoonish cloud slippers, and as he’d bent down to place them on her feet there was a hesitancy and awkwardness that — after a year and half of dating — is no longer present.
After putting the slippers on her own feet, Yoon-seo had caught Joo-won staring at her, and he’d confessed that he thought she looked pretty — a thought he’d definitely intended to keep to himself. However, once his admiration for his work noona was out in the open, Joo-won had run with his confession and countered her “I’m not into younger men” with “I don’t like older women either — I like pretty women.” (Omo, that’s pretty smooth.)
In the present, Yoon-seo is confused by Joo-won’s return. After all, his mother promised to send him overseas, but Joo-won is not the type to sit by idly while his mother tries to ruin his relationship. Instead, Joo-won declares that he’s going to chase after her and cling to her — a statement that is, depending on how romantic you find this fictional set-up, either a massive red flag or swoon worthy moment.
Joo-won somehow convinced Chairwoman Kim that she shouldn’t send him abroad — where he’d just waste away drinking and partying all day to numb the pain of his breakup — and instead give him a promotion. This is, of course, a strategic move on Joo-won’s part that serves two purposes. One, he aims to prove to his mother that he can elevate the company and be successful without being married off to another chaebol family, like his brother, for strategic business purposes. Second, he plans to stick by Yoon-seo’s side so that he’s neither “out of sight” nor “out of mind.”
Flustered by his frankness and informal speech — a tactic that, according to his online search, would make him more attractive to an ex-girlfriend — Yoon-seo reminds Joo-won that she took his mother’s money, but Joo-won is unperturbed that she was so easily bribed. He always knew she liked money, given her work habits, and he — much to my delight — points out an obvious loophole in her deal with his mother. Yeon-seo promised Chairwoman Kim that she would end her relationship with Joo-won, but there was no clause in their verbal agreement that stated she couldn’t get back together with him after the breakup. (Hah!)
And so, Joo-won begins pursuing Yoon-seo in ways that are just as juvenile as Yoon-seo’s initial tactics to try and ditch him. He tags along to team dinners and luncheons in order to gaze fondly at Yoon-seo’s adorable eating habits and covertly grab her hand in the candy bowl at the checkout counter. He sends her love messages via the printer at her desk during late night work sessions, and when the elevator doors close on his foot, he tries to leverage the injury to get a pity date.
Although his tactics fail at swaying Yoon-seo, it’s easy to see how the young (previously undercover) chaebol initially wormed his way into her heart the first go around. He’s genuinely sweet and attentive, but as Yoon-seo discovers via a private elevator conversation with Shi-won, Joo-won had also frequently set aside his own preferences to cater to hers, a new insight that doesn’t sit well with her.
After pushing herself to work while having a cold — because normal office workers don’t have the luxury of taking a day off whenever they want — Yoon-seo passes out in the company parking garage and wakes up in a VIP hospital with a very concerned Joo-won at her side. She objects to the extravagance, which is an extension of his affection and concern for her, and causes Joo-won to drop his happy facade. He admits that he’s having a hard time. It’s not easy being rejected over and over.
If it’s so hard, she wonders, why does he keep doing it? Similarly, why did he accompany her to the movies when he hates dark cramped spaces, and why did he eat spicy food if he doesn’t enjoy it? Because, he responds, he wanted to like the things she liked, and gradually her likes and dislikes became his own. Yoon-seo, in return, expresses her disappointment that he never gave her the same opportunity to learn and appreciate his interests, like opera, with him because he prioritized her preferences over his own.
The revelation that he put forth so much effort to date her softens Yoon-seo’s resolve slightly, and she decides that they should try just as hard to break up. So she offers to eat with him 27 times — the number of meals she owes him — and during that time they should try to gradually wean themselves off one another. Joon-won agrees to the arrangement, but only because he intends to use it as an opportunity to prove that they should remain together.
It becomes very apparent that Yoon-seo’s plan is going to backfire spectacularly in her face with each passing meal. After a year and a half of dating, she and Joo-won are naturally comfortable and playful with each other, and the familiarity makes it easy for Yoon-seo to forget the intended purpose of the 27 meals. Even Chairman Kim, who has someone stalking the couple and taking photos to monitor the status of their relationship, is concerned with the loving way Yoon-seo looks at Joo-won.
However, despite what Chairman Kim may see in the photos, the breakup is weighing heavily on both Yoon-seo and Joo-won’s minds — a fact that becomes very apparent after Joo-won goads Yoon-seo into drinking with him. He indulges in too much somaek and drunkenly asks Yoon-seo, “Do you not like me anymore?” Against her better judgment, Yoon-seo allows her heart to answer him truthfully, “I still like you,” and in response, Joo-won leans in for a kiss.
Joo-won is such a sweetheart who truly loves her. Maybe he’s a bit naive in thinking his love and perseverance can conquer all the obstacles in his and Yoon-seo’s way, but I think he balances out Yoon-seo’s pragmatic approach to life and relationships. I also adore the fact that he doesn’t hold it against Yoon-seo that she accepted his mother’s money — it’s just icing on the cake. Seriously, his little quip about her getting a BOGO deal (money + love) if she dates him was fantastic, and it cemented my love for his character.
Actually, most of the characters in Cinderella at 2AM are pretty fantastic and have already revealed themselves to be multifaceted. Shi-won, for example, may walk around his house in his boxers and boast about all the freedoms he has in his arranged (and presumably loveless) marriage, but the personification of his robot vacuum hints at loneliness. Even Chairwoman Kim, whose own marriage was arranged, is reservedly affectionate to her sons, and her curiosity in Yoon-seo could be the start of her coming around to approving of Joo-won’s chosen partner.
And speaking of Yoon-seo, I really like that she’s a more mature version of the classic K-drama Cinderella who rarely seems to have her shit together because she’s either still in high school or being constantly dumped on by the universe. Contrastingly, even though Yoon-seo didn’t need the money — because her hard work earned her a successful career with enough money to support herself and her high-school-aged brother — she, unlike her counterparts, was the one to take it. And while this decision was made pragmatically (or pessimistic depending on how you look at it) with the belief that the relationship would inevitably end due to dramatic differences in the bank account balances, one has to wonder, give her troubled childhood, how much of her decision was influenced by a her desire to be liked by her future in-laws.
I was initially drawn to Cinderella at 2AM because of its promised subversion of the Separation Bribe trope, but the novelty of the initial setup also had me doubtful that the drama could sustain the story beyond the first couple of episodes. Obviously, it’s still too soon to predict the trajectory or success of this drama, but if it maintains its current balance of romance and comedy while using character development to drive the plot, then I think Cinderella at 2AM has the potential to surprise us all.