I talked with bartender and I got the item, but nothing triggers . Also , I think I got enough affection with Roxy .Main Quest 2 you talk to the Bartender then look around in the alley at night, you should find a broken item, you can have it fixed from the shop.
to increase Roxy's affection of you, you can give her the non functioning Bolter gun & food, you can also talk with her from your apartment once a day.