First of all, this solution is for those who have already completed Episode 2 and noticed that this achievement did not unlock. If you have not finished this episode yet this is not the solution for you.
Allow me by starting with a list of the achievements that did not unlock for me before I realized some did not pop as they should have: (I was nearly complete with Episode 4)
Episode 1Now What?
Episode 2New Morning
Old friends
Episode 3Fresh Fish
Not in Nottingham
I cannot confirm that this will be the same for anyone else experiencing these issues, as well as if there's any other bugged achievements in Episode 4 or 5. Moving forward I'm going to attempt to pop these "bugged" achievements starting from a fresh save as of writing this solution. I just wanted to post this to let everyone be aware that these achievements are potentially bugged depending on the choices you make.
I got the achievement to pop using the following choices:
After popping "Now What?" in Episode 1, I exited to the main menu and started up Episode 2.
*** Spoiler - click to reveal ***
**My playthrough started me off with Pete in the van.**
>How are you feeling?
>[GIVE SAW]
>Opened backpack
>Tried starting van
>Examined radio
>backed out
>Searched box
>[GIVE CIGARETTE]
>[POKE]
>you're going to be okay
>I'll watch out for him
>you're coming with me
>I'll find him!
>1 QTE action
Achievement should pop. Please comment if this worked for you. I will see you next for the attempt at popping "
Old friends".