Another neighborhood that is happening in the evenings is the bar district near the Akasaka Mitsuke station. Hundreds of workers come out from weds-sat night to drink and party. Sunday it’s chill. It’s not too far from Shibuya for work (by Tokyo standards anyway). You can also try to be near Tokyo Train terminal.
Much of logistics revolves around commuting home. That is why people eat and drink and even shop at the train station. Pulling from a bar restaurant is not as easy as it is in other cities, in my experience. From karaoke and bar/nightclubs is better. The trains shut down pretty early. The crazy punk girls in Shibuya almost all leave at midnight on that train. Getting her to stay with you requires leaving her set. That is difficult since social shaming in Japanese culture is a death knell.
Much of logistics revolves around commuting home. That is why people eat and drink and even shop at the train station. Pulling from a bar restaurant is not as easy as it is in other cities, in my experience. From karaoke and bar/nightclubs is better. The trains shut down pretty early. The crazy punk girls in Shibuya almost all leave at midnight on that train. Getting her to stay with you requires leaving her set. That is difficult since social shaming in Japanese culture is a death knell.