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.
when you're name is mike and you are completely retarded. You manage to spell simple wordswrong and you don't understand things until they are explained to you slowly, but everyone still loves you.