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Forget canned pickup “lines” or strange techniques and routines, and stay away like the plague from any ideas you might have about “tricking” the girl into sex – the best approach is a simple one. Mention something you’d like to do tonight (your agenda! If you’ve been walking, you can gradually slow to a stop now.
If she’s enjoying herself in your company (it doesn’t really take that much), she might voluntarily miss her last train or agree to come for “Just one drink.” If it’s after last train time (ish), then most people are out for good.
Strange things happen in the Big Mikan’s witching hours, when the sober, family-oriented, and conservative wardens of civilized society are tucked happily in their futons and dreaming of short excursions to the safe, Japan-approved getaways of Hawaii and Guam.
The changing of the guard occurs frantically around midnight, hordes of belching salarymen trying to hold the beer and gyoza down while mashing onto the crowded final Yamanote line train.
For people waiting or smoking in these areas, you can simply walk up to them and initiate a conversation.
Some might move away wordlessly – this means they are either not interested or waiting for someone – but don’t be disheartened.
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.
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.
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.
Whereas the Magic Hour was characterized by lots of people either heading to, from, or narrowly missing their trains, the Dead of Night is the opposite – most everybody is indoors somewhere.
You might find a few stragglers outside, but by and large, most people have made their ways to a club, karaoke, izakaya, or a bar.