Oh Soo (Zo In-Sung), known as the best gambler in the Cheongdam neighborhood, lives a meaningless life. His parents dumped him at an early age and he lost his first lover. Meanwhile, Oh Young (Song Hye-Kyo) is the heir to a large corporation, but she lives a lonely existence. She lost her eyesight at an early age and her father recently passed away. Their fate soon becomes intertwined.

Oh Soo was abandoned in front of an orphanage as a baby. Later on, he lost his first lover. Now, Oh Soo works with Jin-Sung (Kim Beom), who looks up to him. Meanwhile, there's another man named Oh Soo who takes care of Oh Soo's residence and cooks for him. One day, the employee Oh Soo tells Oh Soo and Jin-Sung that his father is the CEO OF PL Company and he has a young sister named Oh Young (Song Hye-Kyo). Oh Soo and Jin-Sung doesn't take him seriously.

Oh Soo is in a relationship with actress So-Ra (Seo Hyo-Rim). She's obsessed with Oh-Soo, but he doesn't love her nearly as much. So-Ra is about to go abroad for one year for work and she's afraid Oh-Soo will leave her for another woman during this time. She concocts a scheme to frame him for embezzlement.

Meanwhile, Oh Young's father is the CEO of PL Company. She is the heir to the company, but lives a lonely existence. She is blind and separated from her mother and brother after her parents divorced when she was 6-years-old. Now her father is gravely ill. She doesn't trust anyone, especially Hye-Ji (Bae Jong-Ok), who caused her parents to divorce. One day, Oh Young receives a letter from her older brother Oh Soo. From the mailman, Oh Young learns that her brother has sent her letters regularly and her stepmother Hye-Ji has hidden those letters. Oh Young then decides to visit her brother without telling her stepmother. She takes a taxi and asks to be driven to the address written on her letter. The address turns out to be a residence hotel.

Oh Soo wakes up from the sound of his doorbell ringing. He sees a woman standing outside of his room. She tells him that she is "Oh Young," but Oh Soo doesn't recognize her. She then asks him who he is and he tells her that he is Oh Soo. Meanwhile, Oh Soo realizes that she is looking for the other Oh Soo. He tells her that her brother is at an institute and will be back by 3pm. Oh Soo then goes back to sleep. When he wakes up and checks in the lobby, he sees that the woman is still there. Oh Soo approaches her and she asks him to read the letter sent by her brother. Oh Soo now realizes that she is blind. He takes her outside of the hotel and reads the letter to her.

While reading the letter, he notices a group of guys running towards to him. Instinctively, Oh Soo gets up and runs. While Oh Soo is running away, his employee Oh Soo appears and begins to follow him. Shortly later, employee Oh Soo is fatally hit by a car. Oh Soo is then caught by the guys chasing him and Oh Young is standing nearby hailing a taxi cab. She is unaware that her older brother Oh Soo has just died in front of her. Oh Young is leaving because she just received a phone call that her father has passed away.

While Oh Soo sits in prison, So-Ra and her lawyer visits him. They explain to Oh Soo why they set him up. She tells him to spend a year in prison and then live with her in Switzerland for good. She has about 7 million dollars from the embezzlement scheme. Oh Soo tells her that he won't ever go back to her, even if he is killed by the person she swindled.

One year later, Oh Soo is now out of prison. He learns that he has no money left and that So-Ra's sponsor has hired a gangster Moo-Cheol (Kim Tae-Woo) to get back the 7 million dollars he believes Oh Soo stole. Moo-Cheol tells Oh Soo that he has to come up with the money in a 100 days or he is dead.

Oh Soo doesn't have a place to stay so he goes to the rooftop room where his employee Oh Soo lived. While standing infront of the rooftop room a man approaches Oh Soo and asks if he is Oh Soo. After confirming that he is Oh Soo, the man named Jang Sung (Kim Kyu-Cheol) identifies himself as a company attorney for PL Company and a friend of the late company president. He has been searching for Oh Soo, because his blind younger sister Oh Young is all alone. The attorney believes Oh Soo is Oh Young's older brother. Meanwhile, Oh Soo realizes this is could be the way he can repay the money.