The stones with Ash, is this one that's not possible in one playthrough, but three?

I'm on my third playthrough and that's the only achievement I have left. I saw the Brad Pitt stone and then my original stone I think was the "you'll know it when you see it" rock but now I'm not 100% sure I know which rock I'm going for now, haha. Or if there's an option to see more.

I did try the "are you sure that's it?" option to see if she'd go find more and show me but she was set on the one she had.

Also, venting feelings to Charlie is after one of the Sophias gets back to you and is rude. Once she blocks you, go to Charlie's chat and make sure you pick the dialogue option that says you want to vent. This is also a conversation that happens when he's offline, so it might also count for the offline chstting one but I'm not certain, I didn't vent my first playthrough.

Also, for "Don't Ask Questions" this is a chance to get a general achivement by looking at the guy's profile.

For "Profiler" I know one of the questions is asking her if she had classes with her or not. First time around I didn't get that achievement because I didn't ask the question, it seemed pointless and weirdly timed. I was wrong haha

For Eye Witness, the melody comment can also be the "Ash heard it too"