The Young Man
The main character of the poem is the speaker. He is only twenty-two years old, but has been rendered world-weary and bitter by his unluckiness in love. He looks scornfully back at himself only a year ago, when he believed that love was joyful and easy. Now, he realizes that it can hurt, and believes he is doomed to a life of endless sadness, because he has had his heart broken.
The Wise Man
Much of “When I Was One-and-Twenty” is devoted to a quotation from a “wise man” who the speaker heard discussing love. The “wise man” has an extremely cynical perspective—he not only believes love always ends in disaster, but also sees it as a transaction. Although the heartbroken speaker sees this as a wise attitude, the poem presents the speaker as still somewhat naive, and thus casts doubt on the true wisdom of the so-called wise man's cynical perspective.