Yakuza 3 Remastered

When you see someone who looks like someone who looks like a thug or Yakuza member rather they're standing and looking around looking for a fight or if someone is chasing you run out of their aggro range and slowly follow them back to they'll go back to standing still and look at them for a while by clicking in the right stick. If they don't look at you then try slowly inching your way towards them. Look in their direction for 5-10 seconds and they'll eventually run over to you. Do this three times and you’ll unlock your achievement.

The first thing to know when attempting at unlocking this achievement is seeing the visual giveaway of a thug or yakuza enemy within the crowds as a sign that it'll fight you if you get in their field of vision. That giveaway is they'll either just stand around, or walk around very slowly and then just stop. When you see such a character in your view, you need to move Kiryu to a position behind the enemy's back or to the hip, then move up while leaving a few feet of space before then clicking down on to enter first-person mode. Once you do that, just keep your POV centered on the enemy and let it be for about 10 seconds, and they'll eventually turn their back to face you and confront you, where your battle then starts. The achievement will pop after your battle starts from first-person mode for the third time.

I'm including game clips from my playthrough as a visual demonstration. The key is just pacing yourself a little bit slower than normally and getting familiar with particular spawn points for enemies in both Ryukyu and Kamurocho.

This achievement seems to have a bit of a misconception behind it. You don't have to be all that close to trigger a fight.

Thugs, Yakuza, Gangsters etc. will occasionally be standing around looking to pick a fight. As you play you'll start to notice which character models are your enemies (however sometimes they aren't looking to pick fights especially if they're carrying a shopping bad. Even if you know it's an enemy character model the shopping bag will be a dead give away they aren't looking for a fight.)

When you see someone ready for a fight, keep enough distance away to where they won't immediately sprint offer you and click to enter first person.

Now just stare at them for a good 10 - 15 seconds and eventually they'll get bothered and comment on how you're staring at them.

If the fight isn't triggering just get a tiny bit closer. If you get too close they will run at you to which you can run away and wait for them to return to where they are standing. You shouldn't need to get that close however just have patience as you stare them down.