Again. If I'm always broke, how/why do I go out so often? Because. My talent in life is getting away with things, I know how to be cheap, and I have no problem skipping bills and groceries. The fact is, it's extravagant to make a habit of going out on a part-timer's budget, especially in Tokyo. But I can't stay in my room all the time. I would get sad and crazy.
Free: Long walks, libraries, reading magazines in 7/11, sitting in the park, window shopping, nanpa fishing, restroom photography.
Cheap: Flea markets, casual sex, shitty chain cafes like Doutor and Mister Donut, first-time deals at host clubs, Starbucks, one or two drinks at a cozy bar, McDonald's, a small purchase at a crafts store, carefully budgeted house parties.
Overpriced but difficult to live without: kissaten, delicious coffee anywhere (incl. train fare), reasonably low-key nights out.
Painfully out of my price range: Books, music, movies.