Does the speaker seem happy with his choice in "The Road Not Taken" by Robert Frost?

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The speaker's statement that he will talk about his choice "with a sigh/Somewhere ages and ages hence" seems to indicate that he is dissatisfied with his choice of paths.

The poet Robert Frost's Pulitzer Prize‐winning biographer, Lawrance Thompson, quotes Frost as not approving of romantic "sighing over what may have been." By Frost's own admission, the poem was written as a playful mockery of Edward Thomas's seriousness in having such anxiety about which trail to take for a simple walk. Thomas, a friend and fellow poet of Frost's, often worried that whichever trail they did not choose might have had more flora and fauna that he and Frost could have enjoyed.

On the other hand, the final stanza seems to suggest something greater than a mere walk in the woods:

I shall be telling this with a sigh
Somewhere ages and ages hence:
Two roads diverged in a wood and I—
I took the one less traveled by,
And that has made all the difference.

The speaker appears to harbor deep regret about some type of lost opportunity. He is certain that he will retell his story "ages and ages hence," for it is more often remorse than anything else that motivates a person to go back over things in his life. As Robert Marquand writes, there is "a persistent undercurrent of spiritual questioning in Frost":

The poems, in a gentle way, are about the most serious issues of life and death; the poet has an interest in things divine. He is too much a New Englander, a Yankee, and a human to announce this flatly. Not announcing it, in fact, is where his art lies.

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This famous poem by Robert Frost explores both an actual and symbolic pair of paths in the woods. The "[t]wo roads [that] diverged in a yellow wood" offer two paths, and one path is slightly less traveled than the other. The speaker is "sorry" he or she cannot "travel both," but must make a choice. It does indeed seem to be true that the speaker in the poem is satisfied with the choice he/she has made, to take one path and not another. The speaker takes the road "less traveled by" and says "that has made all the difference." Here we see a shift in tense as well, from past tense to future: "I shall be telling this with a sigh, somewhere ages and ages hence." The speaker knows that he/she is making the wiser choice, one that will resonate in memory at a future time. The fact that it will make "all the difference" suggests a realization that taking a road not used as often is a more daring and interesting choice. If one reads this poem as a metaphorical summation of one's chosen path in life, the speaker is offering the opinion that choosing to do things which deviate from the more expected or acceptable social expectations might indeed lead to a more satisfying life.

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