"awkwardest" in the adjective sense
1. awkward
causing inconvenience
"they arrived at an awkward time"
2. awkward
lacking grace or skill in manner or movement or performance
"an awkward dancer"
"an awkward gesture"
"too awkward with a needle to make her own clothes"
"his clumsy fingers produced an awkward knot"
3. awkward, bunglesome, clumsy, ungainly
difficult to handle or manage especially because of shape
"an awkward bundle to carry"
"a load of bunglesome paraphernalia"
"clumsy wooden shoes"
"the cello, a rather ungainly instrument for a girl"
4. awkward, clumsy, cumbersome, inapt, inept, ill-chosen
not elegant or graceful in expression
"an awkward prose style"
"a clumsy apology"
"his cumbersome writing style"
"if the rumor is true, can anything be more inept than to repeat it now?"
5. awkward, embarrassing, sticky, unenviable
hard to deal with especially causing pain or embarrassment
"awkward (or embarrassing or difficult) moments in the discussion"
"an awkward pause followed his remark"
"a sticky question"
"in the unenviable position of resorting to an act he had planned to save for the climax of the campaign"
6. awkward, ill at ease, uneasy
socially uncomfortable unsure and constrained in manner
"awkward and reserved at parties"
"ill at ease among eddies of people he didn't know"
"was always uneasy with strangers"
Source: WordNet® (An amazing lexical database of English)
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