Discombobulate is my favorite word because when I say or write it, my tongue trips over the b's and people ask, "Is that a real word?" when I say it. My fingers stumble and stutter over forming its letters when I write it. In other words, it very often describes me, situations in my life, and quite a few of the people I deal with on a daily basis.
I have come to dislike this word because it has become synonymous with the apathetic shoulder shrug or expressions of I don't know or I don't know AND I don't care.