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Spoilers are unmarked.
The reason Woo-jin fell in love with his sister[]
- ...is because he grew up as a Lonely Rich Kid and was isolated from his peers over it. Soo-ah was the only one who understood his pain and empathized with him. This led to Woo-jin believing that she was the only one worth loving. It's also worth noting that Soo-ah was concerned about her and Woo-jin's reputations, which makes sense when you consider what image rich people are expected to uphold in society.
- At the end of the film he says he has nothing to live for. He may have felt suicidal as a teenager but Soo-ah was the only thing that held him back. Once she was gone, he had no purpose left.
- Or maybe that was because after his revenge he flashed back to his sister dying, he realized that now the last person that caused her death had to be punished, so he killed himself.
- At the end of the film he says he has nothing to live for. He may have felt suicidal as a teenager but Soo-ah was the only thing that held him back. Once she was gone, he had no purpose left.
- ...is because he was hypnotized. It's already established that Woo-jin is from a wealthy family that could afford to send him to America. Due to his position as the heir of the family fortune, it's likely he was the target of rivals who wanted to ruin his reputation/push him out of the competition. A brother having a child with his sister would be a huge scandal, so one of the rival families hired that same hypnotist to make Woo-jin fall in love with his sister.
- This could explain why he insists that it was "Dae-su's tongue, not Woo-jin's dick, that got Soo-ah pregnant". The hypnosis is so far gone that he's too delusional to see it was his own fault.
- ...is a nod to how the original manga that Oldboyis based on is Japanese - a supposed Japanese legend states that star-crossed lovers are reborn as siblings.
- Is because prior to their relationship, there were already rumours that he was sleeping with his sister, so it became a Self-Fulfilling Prophecy.
Woo-jin is a time traveller[]
- He is in his 40s, but looks like he's 26. He also seems to know how to predict the future. He could have used his powers to see the future and invest in whatever caused the dough to roll, hence how he's so rich.
Dae-su didn't forget[]
In the end of the film he begs the hypnotizer to make him forget. But he pulls the same smile he mimicked while going insane during captivity. So the hypnosis failed and he's going insane from coping with what happened.
- Back to Oldboy