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The fifth season of Whenever Possible kicks off with Hwang Jung Min and Jung Ho Yeon in Jungnang-gu. The first guests are the students of Daewon High School. They share the story of how they fell in love with working out at their school’s gym. The second guests are the students of a night school for the elderly. They talk about the passion that led them to study Hangul.

Heo Sung Tae and Jung Hae In join Jae Seok and Yeon Seok in Dongjak-gu. As it's the neighborhood Hae In lived in for over 30 years, he introduces them to local favorites. The first guests are members of a boxing gym who requested a meeting to celebrate the gym's relocation. The second guests are from Chung-ang University's football team, Blue Dragons. They share how they got to join the football team and their dreams after they graduate.

Cha Tae Hyun and Jin Ki Joo join Jae Seok and Yeon Seok in Gwangjin-gu. Ki Joo introduces them to her favorite restaurant as she’s familiar with the neighborhood. The first guest is a member of the local pickleball club. She sent in the request, hoping to get closer to her club members. The second guests are the second graders from Gwangjin Elementary School. They share how they became best friends and what kept them together.

Hyun Bin and Woo Do Hwan join Jae Seok and Yeon Seok in Anyang, where Do Hwan was born and raised. The first guests are a family of four who run a taekwondo studio and a piano academy. Hoping to make a special day for her parents, the daughter wrote to the show. The second guest is an employee at an S Electronics Service Center. Hyun Bin and Do Hwan show off their athletic skills during the games.

Joo Woo Jae and John Park meet Jae Seok and Yeon Seok in the Hongik University area, where Woo Jae went. The first guest is the academy runner for show hosts. As a former show host, he passes his knowledge about selling products to his students. The second guests are two ladies who run an Italian restaurant together. They share the difficulties of running a restaurant in the Hongdae area.

Jae Seok and Yeon Seok visit Cheongdam with Whenever Friends Yoo Seung Ho and Young K, meeting a makeup artist and three pastry chefs. They challenge two unique games to win gifts. First, they have to flick bottle caps to close cosmetic lids, and they have to bounce balls into a chef's hat. Unlike the first mission, the second mission doesn’t seem to be going well. Can this dynamic team win all the desired gifts for their guests?

Byun Yo Han and Roh Jae Won meet Jae Seok and Yeon Seok in Incheon, where the two actors grew up. The first guest is a veteran taxi driver who navigates every corner of Incheon. He shares how he became a volunteer to help with traffic duties. The second guest is a member of the Incheon Philharmonic Orchestra who plays the timpani. Will they be able to win gifts for the Whenever Guests?

This time, Jae Seok and Yeon Seok visit Cheonan with Actor Lee Sun Bin and Actor Yoo Jae Myung. As Cheonan is Sun Bin’s hometown, Sun Bin is so excited to introduce it. What’s more, she even feels nervous because she has to go to her alma mater to meet their first Whenever Guest. Will they be able to win the prize and go back to Seoul with a smile?

Nam Ji Hyun and Kim Jae Young meet Jae Seok and Yeon Seok at Sogang University, where Ji Hyun graduated from. The first guest is a member of Sogang Broadcasting Station. She invited the members, hoping to make their time at the office exciting. The second guest is the owner of a cafe where she makes and sells Korean traditional confections. Will they be able to win gifts for the Whenever Guests?

Chae Soo Bin and Shin Seung Ho meet Jae Seok and Yeon Seok at Gwanghwamun. The first guests are three office workers of different nationalities who assist foreigners who wish to live or are already living in Seoul. The second guest teaches gayageum in Samcheong-dong. She offers one-day classes to tourists and teaches them the history of gayageum as well. Will they be able to win gifts for the Whenever Guests?

Seo Hyun Jin and Lee Chun Hee meet Jae Seok and Yeon Seok in Nowon, where Hyun Jin grew up. The first guests are a son who runs a pharmacy and his mother, who works alongside him. The mother shares the pros and cons of working with her son. The second guests are puppy raisers who give socialization training to guide dogs for the visually impaired. Will they be able to win gifts for the Whenever Guests?

Lee Dong Hwi and Yang Se Jong meet Jae Seok and Yeon Seok in Haebangchon, where Dong Hwi lives. The first guests are sisters who run a Turkish brunch cafe. They share the story of how they settled in Korea. The second guest runs a vintage store, and he shares the reason he fell in love with the color pink. Will they be able to win gifts for the Whenever Guests?