The skydiving part could mean that you often have your "head in the clouds," so to speak, or that you are not thinking rationally in certain areas of life.  This is emphasized by the fact that you land gently without a parachute, which is not a rational thing to happen.  Perhaps you spend a lot of time daydreaming, or dwelling on abstract ideas more than practical ones.  Or perhaps your ego, your perceptions of your abilities and self-esteem, is higher than it should be.

The shaded area represents an area of life that you do not have enough enlightenment about.  You cannot see clearly because you don't have enough information. (It might represent your relationship with this girl, since you explain that you don't know if she likes you in real life.)  I'm not sure about the shack, tower, and wall.  They might represent three places where you see this girl in real life. Or maybe they might be emphasizing the previous idea, that you don't have a good, solid, rational place for your mind to rest, which would be shown by a normal house.  A shack is a small broken-down house, a tower provides shelter but it's not very comfortable, and a wall provides only temporary protection.  Just some ideas.  Kick that around and see what you think...

The girl telling you to stop kissing her might be your dream's way of saying that you should not pursue a relationship with this girl.   You are at the point in your feelings that if you don't nurse them anymore, you can go on with your life without being hurt or negatively affected by her.  Believe me, that can be hard to do, letting go of a crush, but it seems that your dream is warning you.

The dark empty street, again, tells me that you have not settled your mind into a solid rational way of thinking.  You're walking an unenlightened path with no rest and no "life."  What you want to see in the dream is a *house* where you can rest.  And light!  And it seems that you have been living this way most of your life, since you felt in the dream that you had been walking on this road for hours. 

Do you go to public school?  Today's culture preaches such moral-relativism, that many people are confused about reality, right and wrong, and even their own identities.  Maybe the solution for you is to find a group of people, (preferably of multiple generations, not just your own age group) who are upright, strong in their faith, and secure.  Ask them questions.  Hang out with them.  Begin to build your "house" (way of thinking) on a solid foundation, and everything else will begin to fall into place.

Hope that helps a bit!  Best wishes, and I'll pray for you!