Let's see, hopefully this doesn't become too long...
1) Remember that there are going to be guys very much like you (shy). With these guys, it seems like it would take much more work from both of you to really achieve a line of open communication. Maybe good friend material, but not the best boyfriend material for you?
2) Communication requires trust. A lot of people have their own trust issues. In fact, I think it's probably safe to say that there are very few people who are quickly trusting. It often takes time to develop that trust, especially on both sides.
Mostly I guess what I'm suggesting is to pull, don't push. Draw them in, pull them closer to you; spend time with them as casually as you can. You'll be able to understand their personality better and understand whether '1' will be an issue. As you spend more time with them, the trust will grow. They will get to know you too; know that you desire to know their feelings, know that you are trustworthy. Confronting them, pushing them, to tell you their feelings will do exactly that, push them...away. For me personally, I have no problem with a poor communicator as long as they are willing to stick with it and make sure that they are eventually understood. In fact, at some level (to me) a woman that recognizes her short comings and is willing to work on them as part of our relationship would be more attractive than a pretty perfect princess.
Above all else, seek God. It's easy to kind of hide your relationship with God as you focus your attentions on a guy (or on finding a guy). In the end, God knows what is best for you. He will provide for you, and He will provide for you perfectly. Fighting Him, or seeking your own desires will likely just bring pain.