Flummox

Suggested by Adriana S.

Definition: (from dictionary.com)
-verb (used with object)
1. informal. to bewilder; confound; confuse

Examples:

"I spend most of my time in math class completely flummoxed."

"Sometimes I think technology exists just to flummox people rather than help them."

Origin: (from etymonline.com)

"1837, can't word, origin uncertain, probably from some forgotten British dialect. Candidates cluster in Herefordshire, Gloucestershire, southern Cheshire and also in Sheffield. 'The formation seems to be onomatopœic, expressive of the notion of throwing down roughly and untidily.'"

Awkwardness rating: 6

Even Jackie Chan gets flummoxed sometimes. (memegenerator.com)

The Most Awkward Word of 2012: Malarkey

Merriam-Webster has published its "Words of the Year 2012" list and one of the words was featured on the Awkward Words Blog earlier this year: malarkey! This list is compiled based on word lookups on the Merriam-Webster website during 2012. Merriam-Webster defines malarkey as "insincere or foolish talk." It was popularized this year by Vice President Joe Biden during election debates.

Malarkey made the list - and that's no malarkey. (dailydot.tumblr.com)