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lacking skill or dexterity.
Synonyms: clumsy, inept; unskillful, unhandy, inexpert.
Antonyms: deft, adroit, skillful, dexterous; handy.
lacking grace or ease in movement: an awkward gesture;
an awkward dancer.
Synonyms: uncoordinated, graceless, ungainly; gawky; maladroit; clumsy.
Antonyms: graceful.
lacking social graces or manners:
a simple, awkward frontiersman.
Synonyms: gauche, unpolished, unrefined; blundering, oafish; ill-mannered, unmannerly, ill-bred.
Antonyms: gracious; polite, well-mannered, well-bred; smooth, polished, refined.
not well planned or designed for easy or effective use: an awkward instrument;
an awkward method.
Synonyms: unwieldy, cumbersome, unmanageable; inconvenient, difficult, troublesome.
requiring caution; somewhat hazardous:
an awkward turn in the road.
Synonyms: dangerous, risky, unsafe, chancy; perilous, precarious, treacherous.
hard to deal with; difficult; requiring skill, tact, or the like: an awkward situation;
an awkward customer.
embarrassing or inconvenient; caused by lack of social grace:
an awkward moment.
Synonyms: unpleasant, trying, difficult; uncomfortable, ticklish, touchy.
Obsolete. untoward; perverse.
Contemporary Examples

For the Journal, covering it all has been an awkward and frustrating challenge.
Dow Chief Quits in Phone-Hack Scandal Nick Summers July 14, 2011

She would of course always come clean, after everyone enjoyed an awkward chuckle.
The Ongoing Stigma of Interracial Dating Keli Goff September 14, 2014

After an awkward phone conversation, the two met for coffee and married six months later in 2009.
‘True Blood’s Scene-Stealer Jace Lacob July 21, 2011

He remains stiff, awkward, gaffe-prone, and unable to connect with the 99 percent.
Mitt Romney Clinches: What We Learned From 2012 Republican Race Michelle Cottle April 24, 2012

Then he gives an awkward wave goodbye, seemingly unaware of his own.
‘The Social Network’s’ Reluctant Star Anna David September 25, 2010

Historical Examples

“Ah, that would be awkward,” said the American thoughtfully.
The Peril Finders George Manville Fenn

The situation was awkward, and awkwardly he got himself out of it.
Quaint Courtships Various

Tibbitts and the Professor had an awkward experience the first night they were in Paris.
Nasby in Exile David R. Locke

Never in my life did I feel so awkward as then, and it was not strange that you ridiculed me so.
The Dream Emile Zola

Sort of a feckless dub he was, too; kind of honest and awkward—you know.
Merton of the Movies Harry Leon Wilson

adjective
lacking dexterity, proficiency, or skill; clumsy; inept: the new recruits were awkward in their exercises
ungainly or inelegant in movements or posture: despite a great deal of practice she remained an awkward dancer
unwieldy; difficult to use: an awkward implement
embarrassing: an awkward moment
embarrassed: he felt awkward about leaving
difficult to deal with; requiring tact: an awkward situation, an awkward customer
deliberately uncooperative or unhelpful: he could help but he is being awkward
dangerous or difficult: an awkward ascent of the ridge
(obsolete) perverse
adj.

mid-14c., “in the wrong direction,” from awk “back-handed” + adverbial suffix -weard (see -ward). Meaning “clumsy” first recorded 1520s. Related: Awkwardly. Other formations from awk, none of them surviving, were awky, awkly, awkness.