I have a question: I have Bigdaddyhurt sending me a message to go for a walk at 2 am, but nothing happens.

Headpat a sexbot in a dystopian world · By
Why did you mentioning Jun's outfit?
Jun has nothing to do with this event.
If you already used the Lingerie Catalogue, it should trigger when you go for a walk outside alone between 02:00 - 02:59 AM.
If it's not triggering, maybe it's because there are some other event going on. For example, the Riot event.
The Riot event happens around day 30 or more.
"Lingerie Catalogue" is an item that you will get after you tried to throw out bot parts away, decides not to, then input "BigDaddyHurt" for the name of who can help you get rid of the sexbot parts...
"Lingerie Catalogue" will arrive with your next order from BigDaddyHurt's shop...
When your order arrived... Check your inventory for an item called "Lingerie Catalogue" and use it, and it will tells you to go for a walk at "2 AM".
There's nothing to do with an underwear or lingerie underwear that Jun wears, or anything related to Annalie's Clothing shop.
If you are certain that you did everything correctly, then that playthrough might be bugged, and it can't be fixed.
Noted: This step-by-step guide was made for the game version 0.90 and above. We no longer have to wait for his message during streaming.