Being that I live in Tokyo I might be able to help you out a bit. If you like games, Akihabara is the place to go. There are lots of video arcades and game shops, as well as a 5 story sex shop, all near the train station. If you have the money, Roppongi is the place to go for clubs, but if your budget is a little smaller Shibuya has a large selection to choose from. Shinjuku is also a very happening place that I would recommend. Lots of night life there. Restaurants...take your pick...there are tons of them and I couldn't begin to recommend just one or even a few. If you like Japanese food and are brave like I was my first few years here, walk into a Japanes restaurant where the menues are all written in kanji and pick your food by the "point and pray" method. I've rarely been disappointed. Hope that helps a little.
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