OK, I pulled out the game code so I could give you some more specific advice. Try playing as a softer, gentler Ari, and surrendering to the soldiers at the start - if you play your cards right you'll have a good heart-to-heart, and that'll really help out long term. (It's also possible to not surrender to the soldiers and still make it work, but it requires some very deliberate choice-making and is a bit trickier).
You'll know pretty quick if he's into it, because the conversation about how he's into Raeann can go in a direction that it sounds like you haven't seen before.
Good luck!