To take a simple situation and make it so painfully and horrendously awkward or (funny for spectators) that it reminds someone of Michael Scott from The Office.
Jeff told Sasha on the third date that he was madly in love with her. It was a mikestrosity.
Nickname given to bales of marijuana thrown overboard or out of airplanes. Origin is reportedly from members of the US Coast Guard in the area of Southern Florida.