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Bro, how many times do I have to ask Hinata for a massage? I have obedience level 2 and dominance level 1. I've accumulated enough money to be AFK for about 30 in-game days. However, whenever I have the opportunity to ask, she keeps saying she'll think about it. What should I do?

Try going through all her lines of dialog and raise her respect, you can buy her a bouquet of flowers from tenten and gift it to her in the evening in her room to raise her respect faster