The Collaborative International Dictionary of English v.0.48:

Awkward \Awk"ward\ ([add]k"we[~e]rd), a. [Awk + -ward.]
   1. Wanting dexterity in the use of the hands, or of
      instruments; not dexterous; without skill; clumsy; wanting
      ease, grace, or effectiveness in movement; ungraceful; as,
      he was awkward at a trick; an awkward boy.
      [1913 Webster]

            And dropped an awkward courtesy.      --Dryden.
      [1913 Webster]

   2. Not easily managed or effected; embarrassing.
      [1913 Webster]

            A long and awkward process.           --Macaulay.
      [1913 Webster]

            An awkward affair is one that has gone wrong, and is
            difficult to adjust.                  --C. J. Smith.
      [1913 Webster]

   3. Perverse; adverse; untoward. [Obs.] "Awkward casualties."
      "Awkward wind." --Shak.
      [1913 Webster]

            O blind guides, which being of an awkward religion,
            do strain out a gnat, and swallow up a cancel.
                                                  --Udall.
      [1913 Webster]

   Syn: Ungainly; unhandy; clownish; lubberly; gawky; maladroit;
        bungling; inelegant; ungraceful; unbecoming.

   Usage: Awkward, Clumsy, Uncouth. Awkward has a special
          reference to outward deportment. A man is clumsy in
          his whole person, he is awkward in his gait and the
          movement of his limbs. Clumsiness is seen at the first
          view. Awkwardness is discovered only when a person
          begins to move. Hence the expressions, a clumsy
          appearance, and an awkward manner. When we speak
          figuratively of an awkward excuse, we think of a lack
          of ease and grace in making it; when we speak of a
          clumsy excuse, we think of the whole thing as coarse
          and stupid. We apply the term uncouth most frequently
          to that which results from the lack of instruction or
          training; as, uncouth manners; uncouth language.
          [1913 Webster] -- Awk"ward*ly
          ([add]k"we[~e]rd*l[y^]), adv. -- Awk"ward*ness, n.
          [1913 Webster]

WordNet (r) 3.0 (2006):

awkward
    adj 1: causing inconvenience; "they arrived at an awkward time"
    2: 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" [ant: graceful]
    3: 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" [syn: awkward,
       bunglesome, clumsy, ungainly]
    4: 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?" [syn: awkward, clumsy, cumbersome,
       inapt, inept, ill-chosen]
    5: 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"
       [syn: awkward, embarrassing, sticky, unenviable]
    6: 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"
       [syn: awkward, ill at ease(p), uneasy]

Moby Thesaurus II by Grady Ward, 1.0:

145 Moby Thesaurus words for "awkward":
   Latinate, all thumbs, blankminded, blunderheaded, blundering,
   bombastic, boorish, bulky, bumbling, bungling, butterfingered,
   callow, careless, clownish, clumsy, clumsy-fisted, confused,
   contrary, cramped, crosswise, crushing, cumbersome, cumbrous,
   dangerous, delicate, difficult, discomfited, discommodious,
   disconcerted, disconcerting, disturbing, dumb, elephantine,
   embarrassed, embarrassing, empty, empty-headed, fingers all thumbs,
   forced, formal, fumbling, gauche, gawkish, gawky, graceless, green,
   groping, guinde, halting, ham-fisted, ham-handed, hazardous, heavy,
   heavy-handed, hulking, hulky, humiliating, ignorant, ill at ease,
   ill-chosen, impractical, inane, incommodious, inconvenient,
   inefficient, inelegant, inept, inexperienced, inexpert, inkhorn,
   innocent, know-nothing, labored, leaden, left-hand, left-handed,
   loutish, lubberly, lumbering, lumpish, lumpy, maladroit, massive,
   massy, mortifying, naive, nescient, oafish, out of place, perilous,
   perverse, pompous, ponderous, precarious, raw, rigid, risky,
   sensitive, sesquipedalian, shamefaced, simple, sloppy, splay,
   sticky, stiff, stilted, strange to, tentative, ticklish, touchy,
   tricky, troublesome, trying, turgid, unacquainted, unapprized,
   uncomfortable, uncomprehending, unconversant, uncouth, undexterous,
   uneasy, unenlightened, unfamiliar, unfortunate, ungainly,
   ungraceful, unhandy, unhappy, unilluminated, uninformed,
   uninitiated, unintelligent, unknowing, unmanageable, unpleasant,
   unposted, unripe, unskilled, unskillful, unsure, unversed,
   unwieldy, vacuous, wooden