The speaker's dominant assertion in this poem is that it is impossible to find a woman who is both "true" and "fair." This seems to imply that men are forced to make a choice: They can either choose a beautiful woman or a faithful woman—but they can never have both. In fact, the speaker claims, a man could "Ride ten thousand daies and nights" (or over twenty-seven years) and never lay eyes on a woman who possesses both of these virtues. The speaker goes on to argue that if it were possible to find both fairness and faithfulness in one woman, it could never last long. The compact lines of the final stanza deliver the punch of this statement as the poem concludes:

Yet shee
Will bee
False . . .

The finality and certainty of this ending is a pessimistic portrayal of the speaker's generalized perception of women.

Although the speaker's central message is that women are dependable only in their constant inability to remain faithful, he does not suggest abandoning women altogether. In fact, it is important to remember that the introductory stanza provides an entirely different tone, one of a mystical suspension of what is possible. After all, the first line is an imperative, a call to "Goe, and catche a falling starre." This, of course, is a scientific impossibility. Nonetheless, the reader is urged to find something beautiful, extraordinary, and luminous—and to try to hang on to it. This can be symbolic of the women the speaker has lost faith in, but it could transfer to other situations as well.

The speaker then issues a call to "Get with child a mandrake roote." "Get with child" is a term meaning to impregnate, and a mandrake is a type of plant. Therefore, this represents at attempt to impregnate a plant's roots with a human child. Again, this is an impossibility—and again, readers can see the symbolic role of women in this comparison. A woman's fertility is clearly evident in this line, mingled with the image of the mandrake, which was once believed to hold mystical powers. This further mystifies the power of women.

The speaker also asks to be taught to hear the singing voices of mermaids. Yet another mystical representation in this poem, mermaids were believed to be both beautiful and deadly, luring sailors to their deaths. Thus, it seems that the speaker is constantly drawn back to the very thing that taunts him: the lure of beautiful women. This stanza sets up the tone for the rest of the poem.

The speaker is persistent in his quest to find a woman who is both true and fair, even though he himself finds this pursuit impossible. Therefore, his quest can represent the continual pursuit of goals which seem utterly unattainable. Readers are not urged to abandon the pursuit of such seemingly impossible ambitions; instead, they are compelled to reach toward the improbable.

"Teach me to heare Mermaides singing" is an interesting request from a man who is quite cynical of women. A mermaid's power resides in her beauty, which she uses to attract sailors and then kill them. In some myths, mermaids create storms to kill sailors who pass by, displaying a fierce and unpredictable fury which mankind should fear. Yet in this poem, the speaker longs to hear the call of a mermaid. He thus longs to be pulled back, again and again, under the seductive powers of women—even when he believes that no faithfulness can be found in the gender. Though seemingly miserable in his experiences with women, the speaker is inexplicably compelled to continue in his quest toward finding a seemingly impossible combination of virtues in one woman.