Season 1 of That Winter, the Wind Blows premiered on February 13, 2013.

Abandoned by his mother as a child and raised by the Park family, Oh Soo is a notorious gambler in the neighborhood of Cheongdam. After the death of his first love, he is left heartbroken and cold, not caring about anybody else. Soo is then thrown into prison following the unexpected death of his friend who shares his name. A year later, Soo meets lawyer Jang Seong, who came looking for the deceased Oh Soo, the heir of PL Group. When he is given 3 months to pay or die, Soo uses this opportunity to con the last remaining heir of the PL Group, Oh Young, to pay his debt. While pretending to be the deceased brother who was separated from his sister after their parents' divorce, Soo starts falling in love with the blind Young.