Would You Marry Me? follows the story of Kim Woo Ju (Choi Woo Shik) and Yoo Me Ri (Jung So Min), who enter into a fake marriage after Me Ri proposes, aiming to claim the luxurious prize of a newlywed home.

In the series, Bae Na Ra (known for Weak Hero Class 2 and Tastefully Yours) plays Baek Sang Hyun, the managing director of Botte Department Store, who awards Me Ri the coveted "newlywed home." As Woo Ju and Me Ri settle into Botte Palace, Sang Hyun grows suspicious of his lottery-winning neighbors and keeps a careful watch on them throughout the 90-day period.

Shin Seul Ki (The Haunted Palace) portrays Yoon Jin Kyung, a family medicine specialist who has remained single all her life. Jin Kyung is Woo Ju’s soulmate and harbors feelings for him, making her the first to notice the developing dynamic between Woo Ju and Me Ri. 

Having been close to Woo Ju for a long time, her presence introduces a subtle tension that complicates the relationship between the newly “married” couple.

Seo Bum June (The Fiery Priest Season 2) plays Yoo Me Ri’s ex-fiancé, also named Kim Woo Ju. This Woo Ju impulsively got engaged to Me Ri but cheated on her with his colleague Jenny, leading to their breakup. He suddenly reappears in Me Ri’s life just as she enters a fake marriage with bakery heir Woo Ju to win the 5-billion-won newlywed home, creating unexpected chaos and tension.