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When should you talk to creepy guys?

Hi ladies and gents
I have a question and that is, when should you talk to a creepy guy as a woman. So, this guy keeps sending me weird photos but i see he has money and im rather broke, so i wonder should i tell him to have groceries delivered to me? It doesn't really feel really great either when i think of asking but i love moose track icecream from target (its really really good caramel especially) and I am craving!

Or should i ask for a nice dinner? honestly a weird guy trying to get photos from me and flashing me with few sclothing on on snap.
When should you talk to creepy guys?
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