Swashbuckler

Definition: (from dictionary.com)
-noun
1. a swaggering swordsman, soldier, or adventurer; daredevil.

Examples:
"I had a dream I was a swashbuckler and my sword was a giant Twizzler."

"When I was younger I wanted to be a swashbuckler but then I realized being a pirate isn't socially acceptable anymore."

Origin: (from etymonline.com)
"1550s, 'blustering, swaggering fighting man' (earlier simply swash, 1540s), from swash 'fall of a blow' (see swash) + buckler 'shield.' The original sense seems to have been 'one who makes menacing noises by striking his or an opponent's shield.'"

Awkwardness rating: 4

Essential tools for any swashbuckler: Twizzlers. (triloquist.net)

Masticate

Suggested by Chris H.

Definition: (from dictionary.com)
-verb
1. to chew
2. to reduce to a pulp by crushing or kneading, as rubber

Examples:
"On our dinner date he said I was very good at masticating."
"I told him if he used that language at the dinner table he could go masticate by himself."

Origin: (from etymonline.com)
"1640s, from L.L. masticatus, pp. of masticare 'to chew'"

Awkwardness rating: 8

President Obama always masticates politely. (earthfirst.com)

Discharge

Suggested by Mark E.

Definition: (from dictionary.com)
-verb (used with object)
1. to relieve of a charge or load; unload
2. to remove or send forth
3. to fire or shoot (a firearm or missile)
4. to pour forth; emit
5. to relieve oneself of (an obligation, burden, etc.).

-noun
6. the act of discharging a ship, load, etc.
7. the act of firing a weapon, as an arrow by drawing and releasing the string of the bow, or a 

    gun by exploding the charge of powder.
8. a sending or coming forth, as of water from a pipe; ejection; emission.
9. the rate or amount of such issue.
10. something sent forth or emitted.

Examples:

"Bridget was discharged from the hospital shortly after they removed the marble from her nostril."

"Wait. So the yellow discharge coming from the milk box didn't give you a hint it was bad?"

Origin: (from etymonline.com)
"early 14c., 'to exempt, exonerate, release,' from O.Fr. deschargier (12c., Mod.Fr. décharger) 'to unload, discharge,' from L.L. discarricare, from dis- 'do the opposite of' + carricare 'load'. Meaning 'to unload, to free from' is late 14c. Of weapons, from 1550s. The electrical sense is first attested 1748. Meaning 'to fulfill, to perform one's duties' is from c.1400."

Awkwardness rating: 4

Okay, I won't stick them up my nose again. Can I be discharged now? (allwomenstalk.com)

Squirt

Definition: (from dictionary.com)
-verb (used without object)
1. to eject liquid in a jet from a narrow orifice
2. to eject a spurt of liquid

Examples:

"He squirted his water gun at me and totally, like, ruined my hair."

"Someone shook my soda and it squirted all over me when I opened it."

Origin: (from etymonline.com)

"mid-15c., squyrten 'eject water in a jet,' of uncertain origin, probably imitative. The noun is first recorded mid-15c., originally 'diarrhea;' meaning 'a whipper-snapper' is from 1839."

Awkwardness rating: 8

Squirt that gun at me and I'll, like, lose it. (blog.seattlepi.com)

Gaping

Definition: (from dictionary.com)
-verb (used without object)
1. to stare with open mouth, as in wonder
2. to open the mouth wide involuntarily, as the result of hunger, sleepiness, or absorbed
    attention
3. to open as a gap; split or become open wide
-noun
4. a wide opening; gap; breach
5. an act or instance of gaping
6. a stare, as in astonishment or with the mouth wide open
7. a yawn

Examples:
"All the penguins stood gaping as Eduardo claimed he would be the first penguin to fly."
"There was a gaping sinkhole in the middle of the road! Of course I was late to work!"

Origin: (from etymonline.com)
early 13c., from an unrecorded O.E. word or else from O.N. gapa "to open the mouth, gape," common West Germanic (cf. M.Du., Du. gapen, Ger. gaffen "to gape, stare," Swed. gapa, Dan. gabe), from PIE *ghai- (see gap). Related: Gaped; gaping. As a noun, from 1530s.

Awkwardness rating: 5

I told you guys I could fly! (greenhatworkshop.com)

Malarkey

Definition: (from dictionary.com)
-noun, informal
1. speech or writing designed to obscure, mislead, or impress

Examples:
"Don't tell me you love me after I catch you cheating - that's total malarkey."
"She told me the argument in my paper was malarkey. I told her I wasn't hungry."

Origin: (from etymonline.com)
also malarky, "lies and exaggerations," 1924, Amer.Eng., of unknown origin. Sounds like someone's name.

Awkwardness rating: 6

A jar of malarkey. (rain.org)

Spotted Dick

Definition: (from dictionary.com)
-noun
1. (Brit) a steamed or boiled suet pudding containing dried fruit

Examples:
"I have to go to the store to pick up some spotted dick for the party."
"The spotted dick actually tasted better than I expected."

Origin: (from dictionary.com)
Perhaps from the man's name Dick (short for Richard), or from dialect dick pudding. The dried fruit gives it a speckled appearance.

Awkwardness rating: 10

This spotted dick showed up at my parent's white elephant party.