“For of all sad words of tongue or pen,
The saddest are these: "It might have been!"”
Bret Harte wrote a famous parody of this famous poem, "Mrs. Judge Jenkins" in which the Judge marries Maud, and which he ends with the lines:
Maud soon thought the Judge a bore,
With all his learning and all his lore;
And the Judge would have bartered Maud's fair face
For more refinement and social grace.
If, of all words of tongue and pen,
The saddest are, "It might have been,"
More sad are these we daily see:
"It is, but hadn't ought to be".
Maud Muller (1856)
Context: Alas for maiden, alas for Judge,
For rich repiner and household drudge!
God pity them both! and pity us all,
Who vainly the dreams of youth recall;
For of all sad words of tongue or pen,
The saddest are these: "It might have been!"
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John Greenleaf Whittier 47
American Quaker poet and advocate of the abolition of slave… 1807–1892Related quotes

“My tongue, not my pen, is my instrument.”
Conversation with Thomas Jones (7 January 1946), quoted in Thomas Jones, A Diary with Letters. 1931-1950 (Oxford University Press, 1954), p. 540.
1940s

That's when it's really sad.
Rolling Stone magazine/iTunes podcast (December 2005)
On the "chin-up sad" tone of one of his new songs on his upcoming album "Continuum"

La pluma es la lengua del alma: cuales fueren los conceptos que en ella se engendraren, tales serán sus escritos.
Source: Don Quixote de la Mancha (1605–1615), Part II (1615), Book III, Ch. 16, as translated by Henry Edward Watts (1895).

“Aid the dawning, tongue and pen;
Aid it, hopes of honest men!”
"Clear the Way".
Legends of the Isles and Other Poems (1851)

18
Variant translation:
It is a sad thing when men have neither the wit to speak well, nor the judgment to hold their tongues.
As quoted in A Dictionary of Thoughts: being A Cyclopedia of Laconic Quotations from the Best Authors of the World, both Ancient and Modern (1908) edited by Tryon Edwards, p. 560
Les Caractères (1688), De la société et de la conversation

“The pen is mightier than the sword, but the tongue is mightier than them both put together.”