Waka poetry appears in most classical works of Japanese literature, but it is difficult for students to comprehend and appreciate the poems. This is partly because a waka poem only consists of 31 syllables and therefore contains little information. Moreover, the message of each poem is often conveyed through various combinations of rhetorical techniques. In this study, waka poems in authorized textbooks are examined, and a teaching approach is suggested. More specifically, waka poems in “The Tales of Ise”, “The Tosa Diary”, “The Tales of Ima”, “The Tales of Yamato”, “The Tale of Genji”, “The Nameless Selection”, “The Gossamer”, and “The Murasaki Shikibu Diary” are examined in terms of their themes, the relationship between the sender and the receiver of each poem, and the rhetorical techniques used in the poem. This analysis raised the following points: 1) these poems cover a wide range of subjects; 2) they are written in various poetic forms; and 3) a variety of rhetorical techniques are used. Because many different types and forms of poems are presented in the textbooks, to improve students’ understanding of the poetry, it is suggested that the instructor set specific goals in teaching the poetry. In addition, the instructor should introduce the poems systematically and on a step-by-step basis.