hello hello fellow gamer who stumbled upon the same issue! i have answers. make sure your bot is fully dressed- underwears inculded! once that is done, you can ask her.
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Does it matter what kind of clothes she wears? By that I mean the color, like does it have to be a set. I also doubt that i haven't visited the cloth shop enough or that I have not bought enough, It's the 22nd day and I've bought out her entire store for like 5-6 times. The only chat option besides nevermind that I get when I try to talk to the bot is Small Talk
did the shop keep question you about your gf, asking to see her? if yes, then i'm sorry but i got no clue, if no, you can just go in n' out of the shop without buying anything. until she talks about it. then come back until she has her usual dialogue, then if your bot is fully clothed, you'll be able to talk with her.