Do some role playing, you be him, and he can be you. Don't start with his statement that concerns you, get him having fun with it. Have him help you get into playing him. Listen to him as he plays you, but I'm not sure I'd correct him. How he plays you could be as he sees you, or as he wants you to respond. When he's really into it, then say something like "I wish I was someone else.", maybe he can give you suggestions about that feeling then.