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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.
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).
But no matter whether you’ve been drinking since 6pm or are just now sallying forth on the last train for a heroic night on the town, there is no doubt that the trains dictate the pace of the night.
Everybody living more than a couple stops away from the night time destinations knows they have to either go home around midnight, or stick it out until 5am.
Keep in mind that as groups splinter off heading to different train lines, you generally have only until the ticket gates to make a good impression before she enters the station.