THERE YOU GO ANON a very very very shortened version of how I think it would go down given the possibility.
In case it’s unclear to some: Sasori doesn’t actually think that Sakura crying was a sign of weakness. He wouldn’t understand it, sure, but he respects her, and her emotions were the driving factor that brought his change in attitude and ultimately his death. He also knew that using her feelings against her would rile her up and help break her out of the genjutsu, it’s the reason why he was there in the first place. Hope that helps!
sorry for the multiple changes of art style during this comic inconsistency is my middle name