One thing I notice is that you admire much about him in real life and know he is a good caring person, but when he shows up in your dreams it is always traumatic in some way. Perhaps intimacy is threatening to you? Often in dreams a character will have a double role, both representing the external person and representing those qualities within yourself. How would you contrast or compare yourself to him? Do you think of yourself as also sweet and quiet and caring, or not?

The dream starts out with all good qualities, a pleasant fair and thoughts of a character that you admire, but the plane crash interrupts it all. Interesting that eventually you hated the show, like something interrupted your enjoyment of that as well. It seems like this dream is portraying very intrusive experiences in otherwise good experiences.