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Just to expand on XGC Fragnarok answer so you don't miss anyone...

1)There's the guy on the left when you first exit the house and walk down the stairs.
2) The lady ironing when you first enter the house
3) The lady cradling her baby on the couch opposite of (2)
4) The older man straight ahead when you exit the house
5)To the right of (4) is another gentleman, can't remember what he's doing
6)The guy on what looks to be a stair-master
7)The older couple that badmouths you (you can only talk to the lady)
8) On the left before you meet up with Boone there's a dude milking a cow... I missed him the first time, so I thought this would be helpful.

The very start of Chapter 2 you will be in a small area with people in it. You need to talk to all of them.

Heres a video from Achievement Hunter:

1. First person, his name is Andrew, he is cutting. He is on the left of the stairs when you go down.
2. After that you go into a house, there is a woman whisking a bowl her name is Sally.
3. There is a woman holding her baby on the left of the door as you walk in, her name is Janice.
(There are two children asleep in front of her, you don’t need to talk to them.)
4. As you leave the house through the exit there is a man straight ahead of you. He is using a radio and his name is Zach.
5. As you walk off from Zach, there is a man cooking some soup, his name is Carlos. There is also a child outside that you don’t need to talk to.
6. There is a man called Adedayo and he is on a exercise machine.
7. Opposite from him there is a woman raking his plants, her name is Ana. There is also a person next to her you cant talk to.
8. Right before you regroup on the left there is a man called Sid who is milking a calf.

This is a video from TheNeedToAchieve

Gameplay by DreamKiller SKX and Myself - Watch the video if you like what TheNeedToAchieve are doing support them by subscribing.....

-A Dr. Joystickler Video-
This is at the very beginning of Chapter 2. There are 8 total people you need to talk to; any you can't reach or doesn't respond isn't counted.

There are a total of 8 people to talk to.

1)There's the guy on the left when you first exit the house and walk down the stairs.
2) The lady ironing when you enter the first house.
3) The lady cradling her baby on the couch in the same house opposite lady 2.
4) The older man straight ahead when you exit the house.
5) To the right of number 4 is another man cooking.
6) Past the child on the swing is a man on a stepper.
7) At the left of the man on the stepper is a lady.
8) The last one is on left before you meet up with Boone there's a man milking a goat.

Achievement unlocked.