A temporada 2 de Whenever Possible foi transmitida em SBS de mardi 22 octobre 2024 a mardi 21 janvier 2025. Consiste em 12 episódios, o primeiro se chama "Park Shin Hye" e o último "Cha Tae Hyun and Kim Jong Kook in Mok-dong"..
Yoo Jae Suk and Yoo Yeon Seok are here to gift people with luck, whenever possible! The two visit Whenever Guests, who have applied for the show and are relaxing in their spare time, and play games. Each time they win a round, nicer prizes are added to the pool for the guests. However, all the prizes are taken away if the two lose.