as of right now, I believe it's randomized. A lot of people have complained about, so I hope Dontaco can make it easier. But otherwise, nope, you're not doing anything wrong, jus thave to keep working at it.
Possibly talking to he woman at the bar and increasing your charisma may help. Good luck.
It literally doesn't matter which one you pick, you have a 1/3 chance per row of getting a +1. You can save to keep retrying a talk opportunity to try for +2 or greater, but it's random every time, even after reloading a save.
