TOKYO!! I Have never been in both Cities, but New York has always been 'the cool city' Tokyo is newer, not so strict in fashion and style. What I love in Tokyo are the cosplayers and the culture as a whole. I know it from a friend living there. The people are very open in both, I think, but no one could top the kindness of the Japanese! What ever that would be my decision if I would have to choose one of those, but after visiting other big cities, I can't help but to love Berlin the most.
Definately Tokyo. Wanted to go there since I was like 10 years old. That's 13 years ago. XD I want to relish in their dialect and learn more about their culture and enjoy the new sights and sounds and awesomeness! That would be so cool!