The trains inbound from the outskirts of Tokyo, by comparison, are far more peaceful – empty, even.
I can’t say I haven’t taken a brief nap on the overhead luggage rack of an inbound last train to Roppongi before – guilty as charged.
Right next to it, there is a smoking area, and another newer smoking area closer to the koban outside the station exit.
This area is great for meeting people who are either taking a break before leaving for home, after arriving, or after missing their last train.
If you’re a guy – it won’t be as easy, but the existence of such nanpa-shi illustrate that it’s neither strange nor culturally insensitive to talk to strangers on the street – in fact, it is very much a part of Japanese culture.
During this “Magic Hour” probably the single best place to meet women is on the street near the station.
In Shinjuku, these areas are right outside the Kabukicho exit, in front of Alta (with the large TV monitor overhead) next to the fruit shop, and outside the west exit.
In Ikebukuro the West and East exit are both good, although the East exit is more younger “normal” crowds, and the West exit tends to be more salarymen and red light crowds (including workers heading to and from their shifts, if that’s your thing).
The cities (especially Shibuya, Shinjuku, Ikebukuro, Roppongi, and other major stations) are bright and loud with the sound of laughter and lively conversation as people are emptying into the streets from finished nomikais (drinking parties), dinner dates, social obligations, and some unlucky overtime shifts.
Most establishments are open until 5am, and places like Izakaya and Karaoke often have a flat fee for all-you-can-drink / sing / party until 5am.
While I don’t recommend going to an izakaya for the sole purpose of hooking up with someone (unless you’re bringing that someone there), if you are already there with friends you might just find a table of friendly people (or a cute girl/guy on the way to the bathroom) who you can meet and share laughs with.
Whether their night was a success (drinking with their friends) or a feat of endurance (watching the clock until the boss stops drowning them in shochu and forcing them to listen to rude jokes), the transition to last train usually has people in a good mood.
In the smoking area near the Kabukicho exit of Shinjuku station, near 109 and the scramble crossing in Shibuya, and outside the East and West exits of Ikebukuro station, you’ll see the nanpa-shi (pickup guys), standing guard with their standardized uniform – gelled hair, man purse, loafers, and phone in hand – eyeing women from their sentry posts along the main pedestrian thoroughfares.