How to deal with a shy and inexperienced guy?

If you're really interested in him and think he may feel the same way, then go ahead and ask him out. If you're nervous too, maybe try to get a group of people to go out together. That way you can spend time with him and feel comfortable together, but it won't be as awkward if it was just the two of you alone. But there's nothing wrong with taking charge and asking him out. Just don't try to be too forward and make him uncomfortable.