Note: there are probably better options to unlock this, but these are all the dialogue choices I made to unlock the achievement.
-I love festivals
-Do you miss home?
-Laugh it off
-Accept (Note: The Booty Call achievement unlocks here)
-Eat something without using her hands
-What do you think of me?
-Rob a bank (Note: The Smooth Criminal achievement will unlock here)
-Is everything alright?
-Are you talking to other guys?
-I'd like to keep seeing you
Achievement unlocks after the credits, which you can skip with RB.