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After visiting Starcon 3 times you’ll unlock the option to call Anna for outdoor photoshoots.

Locations are:

• Mall [ Requires “Red Outfit” from Zuri’s shop ]
• Downtown Streets [ Requires “Cool Outfit” from Zuri’s shop ]
• Hospital’s Patient Room
• Outside Ken’s House
• Club [ Slut Route ]
• Park’s Bathroom [ Need “Lost Key” from Tasha’s shop ]

You can only call once a day. If it is not working from these locations and you have the routes/outfits it sounds bugged. 

As advised before, if you do have the perk and outfits unlocked but unable to call Anna, is because of a known bug. You'll need to get out of the place and re-enter couple times until it triggers.