See the SENSES SYMPATHY SYSTEM tutorial.
choose new game and then choose the either option (After or Before). after a few minutes of dialogue and scenes an icon will appear in the top right corner of the screen. press Back when you see this icon to open the senses screen. press down to choose the person and then press right until the slider reaches the MAX end and press A twice. after a little more dialog you will get this achievement.
if you want to make the dialog go faster, press X then choose the 5th selection to go into options, press RB twice and go to the third option (the second one that is not a scroll bar). move that option to the right and press A twice to save your settings. now press start and it will skip thru really fast.