Q: “Awkward” is an awkward-looking word, with a “w” on each side of the ”k.” Online sites only categorize it as an adjective, while its brethren and sistren (like “forward” and “backward”) can be adverbs or adjectives. I wonder if it’s related to “gawk” or “gawky.”
A: Yes, “awkward” is an awkward-looking word, one that suits the awkwardness of its various meanings.
That “wkw” in the middle is what sets “awkward” and its derivatives apart. We can think of only one other “wkw” word in English: “hawkweed,” the common name for a favorite wildflower of ours.
John Ayto, in his Dictionary of Word Origins, says “awkward” was coined in the 1300s in Scotland and northern England, where it meant “turned in the wrong direction.”
Ayto writes that it’s a combination of the Middle English adjective “awk” (“the wrong way round, backhanded”) and the directional suffix “-ward.”
The word “awk,” in turn, is derived from Scandinavian sources. The Chambers Dictionary of Etymology cites the Old Icelandic adjective ǫfugr (“turned the wrong way”), while the Oxford English Dictionary says the source is probably the Old Norse afug, öfug, or öfig (“turned the wrong way, back foremost”).
Ayto doesn’t give any citations for the Scottish and northern English origins of “awkward.” But the earliest example of the word in the OED is from a manuscript that includes words in the Northumbrian dialect spoken in the north. The medieval Kingdom of Northumbia covered what is now northern England and southeastern Scotland.
Oxford says “awkward” meant “in the wrong direction, in the wrong way,” when it appeared for the first time in the Middle English poem Pricke of Conscience (1340): “Þe world þai all awkeward sette” (“They turned the world all awry”).
(Though some scholars say the author of the manuscript is unknown, the OED attributes the poem to the English mystic Richard Rolle, who spent much of his life as a hermit in the north of England.)
As for those “brethren and sistren” that are adverbs as well as adjectives, “awkward” was an adverb when it showed up in English. In the 1340 citation above, “awkeward” is an adverb modifying the verb “sette.”
The adjective didn’t appear until the early 16th century, when “awkward” meant “turned the wrong way, averted, back-handed; not straightforward, oblique,” according to the OED.
In the dictionary’s first adjectival citation, from the Scottish clergyman Gavin Douglas’s translation of Virgil’s Aeneid sometime before 1522, the grief-stricken Dido beholds the departing Aeneas “with acquart luke” (“with a sideways glance”).
The “clumsy” sense of “awkward” showed up a few years later. The OED’s earliest example is from John Palsgrave’s L’Esclarcissement de la Langue Francoyse (1530), a French-English grammar:
“Awkwar leftehanded, gauche.” (At the time, “left-handed” meant clumsy as well as “using the left hand more naturally than the right.”)
Over the years, the adjective “awkward” has taken on many other senses.
In the early 1600s, Shakespeare used “awkward” to describe an ungraceful or uncouth action: “With ridiculous and aukward action.” (From Troilus and Cressida, believed written in 1602.)
In a July 15,1665, entry in his Diary, Samuel Pepys used the adjective to describe an ungainly person: “The most awkerd man I ever met withal in my life.”
Since then, the adjective has been used to describe, among other things, embarrassing or inconvenient actions and situations (1709), embarrassed or ill-at-ease people (1713), a difficult action (1860), and someone who’s difficult or dangerous to deal with (1863, as in an “awkward customer”).
Finally, you ask if “gawky” (ungainly) and “gawk” (to stare stupidly) are related to “awkward.” No, though all three words may perhaps have Scandinavian roots. However, the etymology here is uncertain or, as the OED puts it, “difficult.”
One theory is that the adjective “gawky” (1759) and the verb “gawk” (1785) may have been influenced by an earlier adjective “gawk” (1703), which meant “left” and was used in the phrases “gawk-hand” and “gawk-handed.”
The OED says the earlier adjective is apparently a contraction of various two-syllable combining words in northern English dialects: “gaulick-,“ “galloc-,” and “gaulish-.” If you’re thinking that those dialectal terms may come from gauche, French for left, think again. Oxford says that idea has “grave difficulties.”
Another theory is that the 18th-century verb “gawk” may have come from “gaw,” a Middle English verb meaning to stare or look intently. Oxford compares “gaw,” dating from around 1300 and perhaps earlier, to the Old Norse gá (to heed). But this is all very speculative.
from Grammarphobia http://www.grammarphobia.com/blog/2016/09/awkward.html