This question was recently asked to Andrew WK...
"I’m dating a guy who refuses to give up on his dreams of rock stardom. While it’s admirable in a way, I need a little bit more stability if we’re going to make this work. How can I gently break this to him?"
"Don’t you dare say anything to him about giving up his dream. You’re not the right person for him. Never ask someone to give up on their dream just so you can feel more stable. It’s his choice and his choice alone, no matter how ridiculous his dream may seem to you, or to society, or even to himself. Dreams make humans into self-realized individuals. Your only responsibility is to love everything about him, including his dreams. The idea of 'making this work' sounds more like a way to make his life more boring and predictable. At worst, it’s a genuine sadistic desire to control someone else because your own life feels out of control — or a cruel need to dominate and break someone’s spirit for the sake of your own peace of mind. Look for stability and peace of mind inside yourself, and not in your relationships or the dreams of others."