I worked through the dialogue files of the game and found what I'm very confident are the optimal choices to take in dialogue. A plus sign means you just repeat that choice until the end.

Border guard: 14 11 31 Employer: 11 11 11 31 11 Neighbour: 11 11 11 31 1 Gas station attendant: 21 21 1+ Gas station attendant revisited: 11 11 11 32 41 1+