For Valentine's Day 1986, Ted Kooser wrote "Pocket Poem" and sent the tender, thoughtful composition to fifty women friends, starting an annual tradition that would persist for the next twenty-one years. Printed on postcards, the poems were mailed to a list of recipients that eventually grew to more than 2,500 women all over the United States. Valentines collects Kooser's twenty-two years of Valentine's Day poems, complemented with illustrations by Robert Hanna and a new poem appearing for the first time.

Kooser's valentine poems encompass all the facets of the holiday: the traditional hearts and candy, the brilliance and purity of love, the quiet beauty of friendship, and the bittersweetness of longing. Some of the poems use the word valentine, others do not, but there is never any doubt as to the purpose of Kooser's creations.