Smashed my pinky finger in the car door. 1 side of it has been numb for 2 weeks. Will I regain feeling in it? It feels like it's asleep?

Most likely better. Numbness is due to injuring the nerve. Nerves usually do recover from crushing injuries -- of course worse injuries are harder to recover from. It takes quite a long time, though. I think you're finger is going to be ok with more time.
Maybe. Trauma to a finger, such as closing a door on it, can damage the nerves of the finger. These nerves (2 nerves) run down the sides of the finger. It can take weeks or months to determine if these sensory nerves are permanently damaged.