In my experience, you need couple things to do:

To spend a lot of money, that is, buy an expensive thing, go out and take a walk(you can take bread for lesser energy lost), come back, buy another expensive thing, and so on until Annali says, "You said you'd come with a girlfriend, But I don't see her."

You need the bot to like you.

You have to get all parts, legs, arms.

You don't necessarily need a specific outfit, the main thing is to have shoes, something to cover the bottom (a skirt or baggy pants), and something to cover the top (either a shirt or a baggy hoodie). Panties and bras in the game have no meaning except for interactive streams and during sex, decorative. Socks in turn help if the leg parts are of poor quality, they help to hide it.

If everything done right, you need to go and talk with bot about "the possibility of going out with her"(or something like that).

And one more thing, after multiple playthroughs I noticed that Annali starts selling sneakers, only after that you can talk to the bot about the possibility of going outside, and if there are no sneakers in the store, then there will be no conversation. If there are no sneakers, then something is wrong or more work needs to be done. (sounds logical, because before you can go outside, sneakers have no meaning in the game). Consider this as a trigger. 

I know some things I said have already been written by you, but I hope rest of this helps.