Reading Challenge and Philosophy

Thinking about doing this challenge.
https://m.facebook.com/coffeandagoodbook/photos/a.284326781684444.65232.284148681702254/880027748781008

Looks like fun.

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Philosophical debate:

I was watching a television show.
Why is it that,  on a first date,  the person can buy you flowers,  balloons,  food, tickets to entertainment, or even gifts; but if the person gives you money (the equivalent of any of that),  it's a bad thing? It's possibly prostitution. So it's illegal (in many places).

Any thoughts on either topic?
Have a friend that would like to weigh in?