Doesn't sound like a challenge...more of being stuck in small talk zone.Anyway,you could introduce yourself then make a cold read or assumption about her...
Qualification question?How is that a screen
Chase got articles on screening and qualifying over at the site.Maybe take a gander.
In Htmgc there's a section on being challenging.Don't be too much a challenge and don't be less of one either.Hurts your attainability.
Again "and what does that mean'' doesn't sound like a challenge or a ''get to know you" question.If you would like to get past small talk you could ask her something like ,"What quality best describes you,Roxana?"Then ask her why she thinks of herself as such.
You kinda challenge her to show you why she would think of herself as "worthwhile" ...say if she talked about a great quality of hers.
All in all,it's the balance that does matter when being a challenge.Fundametals too .You ain't going around challenging hot chicks with poor fundamentals.They wouldn't care.Some may but not most.