Five Most Dreadful Dates in Tokyo

Take a walk on the wild side and treat your date to a real surprise.  


Where no girl wants to be alone for any measure of time, Kabukicho is the last place couples will want to go for a quite romantic evening.

Things start off in high gear when streams of handsome wildly dressed young men step in front of your date and to smooth talk her into following them into their bar to have a few drinks with the customers inside.

While she tries to force her way through you yourself will be beset on all sides by Japanese speaking foreigners who flash pictures of their club’s best girls, hopping to entice you to stop by.

After forcing your way past the hordes of hustlers you’ll have to take care not to bump into any of the knots of gang members of mafia who dot the streets lest you be damaged by them. 

At last you’re through and you can now avail yourself of Kabukicho’s quality entertainment options, including: gambling at a pachinko parlor, a show at a strip club, and drinks at any of the ubiquitous hole-in-the-wall pubs.

She’ll be begging you to take her again.

Tsukiji Fish Market

If the homicidal forklift drivers don’t make her run for the exit then the omnipresent stench of fish certainly will. The Tsukiji Fish Market defines smelly and dirty.

The complex is full of excitement, such as fishermen violently chopping off fish heads on make-shift cutting boards (or better yet, chopping off bloody octopus tentacles), workers dragging 300 lbs tunas across the dirty floor and mounds of wiggling squirming squid.

After dodging a few forklifts and other personal vehicles you can find solace in some of the best sushi restaurants in the City. Being just caught hours before there is no contest.

While making it out alive you can minimally expect her dressed to be spattered with fish brains.

Maid Café

Certain to make your date the most uncomfortable she’s ever been in her life a Maid Café is no place to bring your family, friends or much less your girl.

An establishment created to feed the fetishes and pseudo-perverted appetites of the socially-inept, virtually the only individuals who frequent these establishments are geeks and perverts.

This becomes evident after you step inside and are greeted as ‘their master’ and you take in the pink Hello Kitty wall paper, doll houses, lace-decked walls and of course the girls, dressed in embellished French maid costumes.

The fun begins after you are seated and your ‘maid’ holds hands with you while she says some magic words and blows lasciviously on a heat sensitive electric candle light. Still confused and with your eye brows raised your maid will provide you with a menu and ask if she can give you a love injection. Before your date screams out in protest, don’t let her get the wrong idea, its simple a specialty menu item: an omelet with a heart shaped splatter of ketchup.

Trying hard to survive the maids singing Jpop karaoke your wits and patience finally break when your maid comes to your table and offers you to lay your head in her lap while she cleans the insides of your ears. 

All in all a very awkward time.


Not only one of the most dreadful dates but possibly the most dangerous. Chances are strong that you will be stopped by the local gangs and interrogated as to what and why you’re there. Your answer will determine your well being, for if you ask the locals they’ll tell you: “you’ll get damaged!”

If you and your date can survive walking through the area without being damaged (which is half the fun of going there) you can avail yourself of the local entertainment: massage parlors, brothels and other houses of shame.

All in all an exciting and death defying adventure. 

Yoshiwara is Tokyo’s original Red Light district, whereas Kabukicho now holds that title, Yoshiwara is still very much in business. 


Once you’ve reached your limit strolling through the infinite number of Traditional Japanese gardens in Tokyo, switch things up a bit and take your date for a stroll through the Tokyo’s slummiest slums through San’ya; where at any given hour you’re guaranteed to find bums and drunks lying about the streets in various states of consciousness.

If money is tight you and your loved one can take advantage of the many soup kitchens and relief centers for a free meal. But under no circumstances attend any of the laborer’s rallies and protests, for you may get stabbed by the opposition.

A room for the night is very inviting at 1500 yen (about $15 USD). Cheaper than a Capsule Hotel you’re bound to keep coming back for more, just be sure to be careful not to trip on the bums on your way in.

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