Lol :O_O
You guys are funny
But seriously , you can't plan things to happen . Just talk about what's on your mind , then one thing will lead to another . If you ask him a question , be interested in his answer and then make that lead to another . Also , you say he wants you to be comfortable , well don't act shy . Open up and be yourself . If you are loud and funny , use some jokes to lighten the mood . If you are shy then take this as an opportunity to grow as an outgoing person .