I would say yes, but it has to do with the worldview from which you ask these questions. If you are asking these questions from a Christian worldview, you will be fine because you have a solid faith and belief in God and Truth (with a capital T). However, if you are coming at these questions from a postmodern or nihilistic perspective, you might just join the ranks of some of the greatest philosophers who associated themselves with these groups. If you have no firm belief in reality, and believe that life is essentially meaningless, then questioning the reality of everything could most definitely lead to a hopeless, despondent despair. If you have no purpose in a meaningless universe, why bother living?