You'll have more fun when you can take a risk without obsessing over everything from trivial concerns to your worst fears. This may come in the form of thinking through every single possible contingency, which is good for some things in life and not so helpful for others. It's good for things like marketing campaigns and investigative reporting. Love, friendship, art, and music require far less cerebral strategizing. The problem is that once your particular mind gets hold of something, it doesn't like to let go—and this is especially true when there is some chance to be taken, or even some relatively minor unpredictable factor. You could tidy up this situation by considering the theme of emotional boundaries. Whatever the source of your anxiety or concern, you'll feel better and be stronger if you define some space and time wherein you're free to be yourself. That's the space where anything can happen, and it's okay—you can go with the flow of your creativity. Then I suggest you do the same thing with selected friends. Choose the people around whom you can "risk" being yourself, which means being fully present with your ideas, your passion, your creativity, and your sexuality. You may not find many people you can experiment with, though you may find a few—the most significant one being yourself. With dropping inhibitions, practice goes a long way.