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Frost spent the years 1912 to 1915 in England, where among his acquaintances was the writer Edward Thomas. Thomas and Frost became close friends and took many walks together. After Frost returned to New Hampshire in 1915, he sent Thomas an advance copy of "The Road Not Taken." The poem was intended by Frost as a gentle mocking of indecision, particularly the indecision that Thomas had shown on their many walks together. However, Frost later expressed chagrin that most audiences took the poem more seriously than he had intended; in particular, Thomas took it seriously and personally, and it provided the last straw in Thomas' decision to enlist in World War I. Thomas was killed two years later in the Battle of Arras.
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"The Road Not Taken" is a narrative and autobiographical poem consisting of four stanzas of iambic tetrameter (though it is hypermetric by one beat – there are nine syllables per line instead of the strict eight required for tetrameter) and is one of Frost's most popular works. The poem, besides being among the best known, is also one of the most misunderstood. 
The final lines "I took the one less traveled by / And that has made all the difference" are often cited[by whom?] as emblematic of America's individualist spirit of adventure, in a reading that assumes they are to be taken literally. But whatever difference the choice might have made, it was not made on the basis of a discerned difference between the two paths that opened up before the traveller. The speaker admits in the second and third stanzas that both paths may be equally worn and equally leaf-covered, and it is only in his future recollection that he will call one of the two roads, the one he took, "less traveled by."
The "sigh" can be interpreted as one of regret or of self-satisfaction; in either case, the irony lies in the distance between what the speaker has just told us about the roads' similarity and what his or her later claims will be. Frost might also have intended a personal irony: in a 1925 letter to Crystine Yates of Dickson, Tennessee, asking about the sigh, Frost replied, "It was my rather private jest at the expense of those who might think I would yet live to be sorry for the way I had taken in life."
According to Larry L. Finger's analysis, nearly all critics have agreed that the sigh represents regret as this is mirrored in the regretful tone of the opening lines. He quotes scholar Eleanor Sickels as saying that the poem is about "the human tendency to wobble illogically in decision and later to assume that the decision was, after all, logical and enormously important, but forever to tell of it 'with a sigh' as depriving the speaker of who-knows-what interesting experience."
Likewise, Frost's biographer Lawrance Thompson is cited as saying that the speaker of the poem is "one who habitually wastes energy in regretting any choice made: belatedly but wistfully he sighs over the attractive alternative rejected."
While a case could be made for the sigh being one of satisfaction, given the critical support of the 'regret' analysis it seems fair to say that this poem is about the human tendency to look back and attribute blame to minor events in one's life, or to attribute more meaning to things than they may deserve.
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