Chortle

Definition: (from dictionary.com)

-verb (used without object)
1. to chuckle gleefully
-verb (used with object)
2. to express with a gleeful chuckle
-noun
3. a gleeful chuckle

Examples:

"The birthday girl chortled as she opened her gifts."

"The woman started to chortle uncontrollably when the millionaire proposed to her."

Origin: (from etymonline.com)

"coined 1872 by Lewis Carroll in 'Through the Looking Glass,' perhaps from chuckle and snort. Related: Chortled; chortling. As a noun, from 1903."

Awkwardness rating: 7

Finally landed myself a rich one! I'll chortle all the way to the bank! (zazzle.com)

Gnaw

Definition: (from dictionary.com)
-verb (used with object)
1. to bite or chew on, especially persistently
2. to wear away or remove by persistent biting or nibbling
3. to form or make by so doing
4. to waste or wear away; corrode; erode
5. to trouble or torment by constant annoyance, worry, etc.; vex; plague

Examples:

"In the summer I look forward to gnawing on corn on the cob."

"Why does my dog gnaw on my shoes so much?"

Origin: (from etymonline.com)

"Old English gnagan (past tense *gnog, past participle gnagan) 'to gnaw,' a common Germanic word (cf. Old Saxon gnagan, Old Norse, Swedish gnaga, Middle Dutch, Dutch knagen, Old High German gnagan, German nagen 'to gnaw'), probably imitative of gnawing."

Awkwardness rating: 3

I would never gnaw on your shoe!

The Most Awkward Word of 2013: Sequestration

Chosen from the Global Language Monitor's 14th Annual Survey of Global English. Sequestration became popular in 2013 due to its association with hotly debated automatic federal budget cuts.

Definition: (from dictionary.com)

-noun

1. removal or separation; banishment or exile
2. a withdrawal into seclusion; retirement
3. law
a. the sequestering of property
b. confiscation or seizure
4. chemistry. the combining of metallic ions with a suitable reagent into a stable, soluble complex in order to prevent the ions from combining with a substance with which they would otherwise have formed an insoluble precipitate, from causing interference in a particular reaction, or from acting as undesirable catalysts

Examples:

"After chewing on her owner's shoes the puppy faced sequestration to the backyard."

"When the waitress was asked to clean up an accident in the bathroom, she decided it was time for sequestration from her job."

Origin: (from etymonline.com)

"c.1400, from Late Latin sequestrationem (nominative sequestratio) 'a depositing,' noun of action from past participle stem of Latin sequestrare (see sequester)."

Awkwardness rating: 6

I contest my sequestration with these sad puppy eyes. (cutearoo.com)

Twizzle

Definition: (from wikipedia.org)
-noun
1. "a multirotational one-foot turn in figure skating"
-verb
2. to perform "a multirotational one-foot turn in figure skating"

Examples:
"The exceptional twizzle was undoubtedly the reason they took the gold."
"She twizzled her way into the hearts of millions."

Origin: (from etymonline.com)
"'to twist, form by twisting' (transitive), 1788, apparently a made-up word suggested by twist."

Awkwardness rating: 5

Twizzle champions. (fansided.com)

Gesticulate

Suggested by Chris H.

Definition: (from dictionary.com)
-verb (used without object)
1. to make or use gestures, especially in an animated or excited manner with or instead of speech
-verb (used with object)
2. to express by gesturing

Examples:

"Chris frequently gesticulates during his stories and knocks things over."

"Charades is a great time to show off how well you can gesticulate."

Origin: (from etymonline.com)

"c.1600, from Latin gesticulatus, past participle of gesticulari 'to gesture, mimic,' from gesticulus 'a mimicking gesture,' diminutive of gestus 'gesture, carriage, posture (see gest)."

Awkwardness rating: 9

He can gesticulate with the best of them. (community.sparknotes.com)

Teensy-weensy

Definition: (from dictionary.com)
-adjective
1. tiny; small

Examples:

"The only kind of bug I like is the teensy-weensy kind."

"My teensy-weensy puppy has grown into a behemoth!"

Origin: (from etymonline.com)

"1825, alteration of tiny; teeny-tiny attested from 1867. Alternative form teensy is attested from 1899 (teensy-weensy is from 1906). Also teenty (1844)."

Awkwardness rating: 8

I used to be teensy-weensy like you. (lifesabundance.com)

Phalanges

Definition: (from dictionary.com)
-noun
1. a plural of phalanx (anatomy. any of the bones of the fingers or toes)
2. plural of phalange

Examples:

"I got all the phalanges in my hand broken when I was little and fell off my bike."

"I'm frozen all the way down to my phalanges!"

Origin: (from etymonline.com)

"mid-15c., 'phalanx, ancient military division,' from Middle French phalange 'phalanx' (13c.), from Latin phalangem (nominative phalanx); see phalanx. It is the earlier form of this word in English."

Awkwardness rating: 6

Even kittens need to keep their phalanges warm. (popscreen.com)