Nice idea to make a game where you have to talk your way through and redo it to get the conversation right. I felt that the choices weren't really that interesting though - like nothing here really required you to have replayed the game to know what to say (except maybe the present thing, but even then you are allowed to back out of your wrong answer). I won on my first try just by being nice instead of mean.
Would be more interesting if there were things you have to know that aren't obvious to not offend them, like if you mention their partner, you learn that they broke up and now they're upset with you, so you have to go back and avoid that topic.