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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.So what’s the hookup timeline of a late Tokyo night?When and where is the best place to hook up with someone in Tokyo?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.Okay, so it might be a little more than an hour but the idea is the same.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.

Then, when they approach simply smile and demurely mention you’ve missed your last train.

If you end up talking to one for a while, you want to determine what her/his plans are for the night.

If they are waiting for a friend you could either try to get their contact information for another day, or alternatively, try to befriend the friend when they arrive and join the party for a drink!

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.




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