This is semi story related, but only pops if you don't choose the dialogue options in the correct manner to take the paths in the Spoilers below. As long as you choose the different path at least once, you'll get this achievement.
You'll want to go into the Options and change Skipping from "Seen Text" to "All Text". Max out the sliders for Text Speed and Auto Speed also, for good measure. Then go back to main menu and click START.
You can fast-forward through most of the dialogue by clicking many times on the double triangles in the lower right of the screen. It stops at times when a dialogue choice is necessary. But then you can keep clicking through. Or... Lots of people like the story, so give it a read if you're interested in it.
The other 2 achievements depend upon the path you take with dialogue choices spread throughout the game. So you will have to play through the story twice more to get both of the following achievements.
Leslie's route
*** Spoiler - click to reveal ***(in the Agency office)
Don’t worry. I’ve got this.
(in the speakeasy/bar)
Spit it out.
One’s enough for me.
I don’t know, something sweet?
(in the Agency office)
…and he flirted with me.
Eavesdrop on the politicians.
…how adorable you are.
I definitely don’t wanna forget it.
Meyer's route
*** Spoiler - click to reveal ***(in the Agency office)
I worry about you too…
(in the speakeasy/bar)
Swallow.
Is there any better stuff…?
…Whiskey.
(in the Agency office)
…and he seemed important.
(in the back parlor of the speakeasy)
Ask about his history.
Ask what his favorite activity is.