Why is my pinky always asleep? Is it something serious?!

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I've actually had something similar to this happen to me. I had my pinky & ring finger go numb for VERY long periods of time. A doctor explained it to me when I had it checked out. You have a bundle of nerves that runs over the curve of your elbow. When this bundle gets pinched for long periods of time (say, like sleeping on your chest with your arms under you, like I was doing), it causes the outer fingers to go numb. this is the same bundle that if you hit just right, makes you yelp in pain (your funny bone anyone?).
My advice, try sleeping on your back instead. If the problem still persists go have it checked out.

Could be a circulation issue.

try this, pinch your pinky finger (on the nail) between the thumb and forefinger of you other hand.
The nail bed will "blanch" or go white. (Take off the polish first wise guy).
It should take less than a 2 count to return to normal (the same as the rest of them).

If it takes a lot longer, its a circulation issue, see a doctor to discuss it further.

If it returns in a 2 count or less, it may be an irritated nerve ending. Does it function ?
Can you move it the full range like the other side ?
Does it have full sensation ? Hot? Cold ? Sharp ? Dull ? If it does, then its a "who knows ?" and unless it gets worse "who cares ?"

LOOOL i think you're talking about pins & needles