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Check the FAQ for 0.80

I dont think premium program is linked to a day. I think it might be linked to amount you spend at her store, and maybe whether or not you come there with Jun. It happened around day 18 for me. Not sure what happened with the skirt for you, it could be a bug, or you're just very unlucky. I hope you can get it soon

I got them by just going to the clothes store. They are called sneakers (also you need to unpack them before using if you buy them)

Patchnotes for the new version mentioned ending related to bot being found. I tried going outside with the bot without high-tech hypercamo skin, but I didnt get any results. Am I supposted to do something else? 

in browser simply type 'iamacheater' (without .ic)

To go outside with a bot you need to speak with lady from clothing store about it (just keep coming to the store for a while and she will ask about your girlfriend). Bow tie isn't necessery in order to go outside, but a skirt is, I hope you can get it if you keep coming there, I know no particular way to find it, sorry. After going to clothing store for a while, if you buy a lot of clothes, you will get access to premium program where you could get any piece of clothing you want.

To go outside you need to talk to the girl from clothing store. At some point she will ask you to come with your girlfriend, and you could talk about it with Jun. It happened around day 15 to me. I think you need high tech hypercame skin for it, but Im not sure.