what should i ask to start a long conversation that a guy would be interested in?

okay i like this guy. he doesnt play sports and al that junk. hes pretty much exactly like me. (the whole skinny jean, music loving person) he sings in a band with his brother and we have talked alot on text but when we talk in person things gets awkward and i cant keep the convo goin. he knows i like him and he said he def needs to talk to me more. i dont want him to get bored. hes not a shy person at all but he is around me, and pretty much only me. grr. this is really important so people please help!

btw im like really shy but im tryin to work on it...