Ok this achievement was tricky and most of the gamers that completed it really couldn't remember the sequence of questions to ask so it took me some trial and error .
As you arrive to the bookstore and speak to slappy pick these 5 options
1) give name
2)finish his thoughts
3)bluff
4)really
5)pry
Achievement unlocks . If you have any question on the game hit me up on live or on ta. This game can be quite tricky.