This achievement requires you to ask the computer to allow you to manually 'skip' when the time comes, instead of letting the computer do it for you.
However, the only
way to unlock this dialogue option is to have a BELOW AVERAGE
Intelligence attribute, so as to unlock the 'Dumb' dialogue options. The only way to alter attributes is through character creation or flaws (alongside certain pieces of clothing, but none alter the Intelligence attribute)
The only ways to get this achievement are:
-- Create a Character with Below Average Intelligence
-- Create a Character with Average Intelligence and then, though the course of gameplay, accept the "Permanently Concussed" flaw, which lowers the mind attributes by 1.