This trophy is missable. However, you are forced into a dialogue with Hugh Darrow near the very end of the game so you cannot miss the opportunity to get the trophy.
This battle of wits is story-based and unmissable, the chance to get this achievement however, is very much so.
If you have the Social Interface Augmentation then choose:
Extrapolate > Appeal > (Pheromones) Omega option
If not then choose:
Extrapolate > Appeal > Extrapolate > Extrapolate
I always had the Social Interface Aug by the end of the game since I was running out of useful places to put Praxis kits. Unless you really don't want that Aug you should most likely have it.