Share your awkward experiences.

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I recently asked a friend I had a crush on out for dinner, and she said NO, and said that I had gone too far and the situation was now awkward.
And I thought, "No it's NOT! ..."

Trying to continue on with a live play when the sound guy queues the fight-scene music too soon: That's awkward.
Getting caught signing a name that isn't yours: Awk Ward .
Accusing a friend of stealing your laptop, and harassing him incessantly for a week before you discover it was someone else: That's awkward.
Tutting (dancing) on your bike while riding towards headlights, then realizing it's a cop car, is awkward, as is pulling mad screeching donuts in an empty parking lot, and squeeling to a stop JUST as a cop car headlights peer over the hill at you.
Finding your roommate's guests snorting lines of cocaine off of your desk: Now THAT's awkward.
Convincing your landlady to evict zed sleazy roommate, and then bumping into him on campus two weeks later to discover he's still homeless, because of you: That's shivers-down-your-spine awkward.
(All those things happened to me.)

Needless to say, my trivial misunderstanding with her didn't even register on my awkwardometer.
In fact I told her all of that in an email reply. (I also said I would leave her alone from now on.)

Anyways, this got me wondering: What are your most awkward experiences?