There has been an increase in the number of Japanese people who disagree with traditional gender roles which has resulted in diversified male roles. Based on a nine-male-roles model, this study examined the chronological changes and differences in male characters as per their ages and relationships with the heroine in NHK’s morning drama serials known as “asadora,” which is a Japanese TV drama. Results indicated that the roles of middle-aged men evolved from “high communion” in the ’60s and ’70s, to “high social status” in the ’80s and ’90s, to “commitment to household responsibility” in the ’00s and ’10s. Meanwhile, young men’s roles evolved from “high agency” in the ’90s to “attentiveness to women” in the ’10s. Additionally, the heroines’ husbands, ex-husbands, male friends, and romantic partners demonstrated “low effeminacy,” “superiority to women,” and “attentiveness to women.” Conversely, the heroines’ brothers, sons, and neighbors demonstrated “psychological and physical strength” and “emancipation from emotional restriction and toughness.” Based on social changes in Japan, implications of this study and future prospects were discussed.