Note: there are probably better options to unlock this, but these are all the dialogue choices I made to unlock the achievement.
Before the date begins when you are talking with Callum, make sure to choose to drink. This will also unlock the Hold my Beer achievement.
-Sounds good to me
-Single for awhile
-Where are you going?
-Love the 1920s
-Had a one night stand
-Lied about my age
-Are you talking to other guys?
-You matched my friend (Note: The Interrogation achievement unlocks here)
Achievement unlocks after the credits, which you can skip with RB.