Tokyo is not an unfriendly city. It is a private one, and the difference matters more than any other thing you will read about meeting people here.
Colombians will talk to you at a bus stop. Tokyoites will not, and it is not coldness — public space in Tokyo is understood as shared space where you keep to yourself so that thirty million people can live on top of each other without friction. The warmth is real. It is just held behind a door, and the door has a handle. Most travelers spend a week in Shibuya without ever finding it.
Here is where the handle is.
Where you stay decides who you meet
This is the decision that quietly settles your whole trip, and it gets made on a hotel-booking site before you have any idea what you are choosing.
Shibuya and Shinjuku are where you will end up if you book on convenience. They are spectacular, and they are also where every other visitor is. The bars nearest the stations are staffed and filled by people who deal with tourists all day. You can have a wonderful week there and speak to no Tokyoite who was not paid to speak to you.
Koenji, Shimokitazawa, Kichijoji — twenty minutes west on the Chuo or Keio lines — are where a lot of Tokyo's actual social life happens. Small bars, secondhand shops, live houses, and crucially a customer base of regulars rather than visitors. Nakameguro and Sangenjaya do the same job to the south.
You do not need to stay in these places. You do need to go to them at night, which most people do not because the guide told them Shibuya Crossing was the thing.
The counter seat is the entire trick
If you take one thing from this article, take this.
In a Japanese bar or small restaurant, sitting at the counter rather than at a table is a different social act. The counter faces the master — the owner-bartender-cook — and sitting there is an implicit opening. Regulars sit at the counter. Conversation happens along it. Tables are for groups who came to talk to each other.
A place with eight counter seats and no tables is the single highest-probability room in Tokyo for meeting someone. It is also the room most travelers walk past, because it looks intimidating and closed. It is neither. It is small, which is not the same thing.
Order something quickly, do not ask for an English menu before you have said good evening, and let the master decide when to talk to you. He usually will.
Standing bars and yokocho alleys
Tachinomi — standing bars — are cheap, fast, and social by construction. Nobody sits, everyone is shoulder to shoulder, and turnover is high enough that awkwardness has a natural exit. Look for them under railway arches, especially around Yurakucho, Shinbashi and Ueno.
Yokocho are the narrow alleys of tiny bars. Ebisu Yokocho is the most useful one for a visitor: communal tables, genuinely mixed crowd of locals and foreigners, loud enough that talking to strangers is normal rather than intrusive.
Golden Gai in Shinjuku is the famous one, and it is worth seeing, but it is a poor first move. Many of its bars are six seats, charge a seat fee, and are effectively private clubs for regulars. Some display no-tourist signs. Go there on your third night, once you have a feel for how these rooms work, not your first.
What does not work
Being honest about this saves you evenings.
Striking up conversation on trains, in queues, or in cafes reads as intrusive rather than friendly, and you will get a polite non-answer. Large clubs in Roppongi are a foreigner economy and you will meet other tourists. Sento and onsen are quiet by convention and not social spaces, whatever the guidebook says about bathing culture. And approaching people on the street, in a country where street-approaches are almost always a sales pitch, gets you read as a sales pitch.
Language: less than you fear, but the right ten phrases
You do not need conversational Japanese. You need enough to signal that you are willing to meet halfway, which is a different and much smaller thing.
Good evening as you enter. Asking what the master recommends. Saying something is delicious and meaning it. Asking what someone is drinking. Thank you when you leave. Ten phrases, delivered badly, do more work than fluent English, because the effort is the message.
Translation apps are completely normal here. Nobody thinks less of you for using one at a counter. Half the regulars will lean over to see what it said.
The problem nobody admits
Here is the honest limitation of everything above.
The way Tokyo actually works is repeat visits. You go to the same eight-seat bar four Thursdays running, the master starts remembering your drink, the regular next to you starts nodding, and somewhere around the fifth visit you are a person rather than a customer. That is a beautiful system and it is completely unavailable to someone here for five nights.
Which is why most travelers to Tokyo, including thoughtful ones who did the reading, go home having eaten superbly and spoken to nobody.
The shortcut
The shortcut is to skip the four Thursdays by going with someone who already has them.
A Tokyoite who takes you to their local does not just take you to a better bar. They change what you are in the room — you arrive as somebody's guest instead of a tourist who wandered in, and the master treats you accordingly. The door that takes five weeks to open is already open, because it was never closed to them.
That is the whole reason Roavi exists. Not a tour, not a guided walk with a flag. Somebody who lives in Koenji, likes their neighbourhood, and is willing to spend an evening showing you the version of it they actually use.