So I came across a neat tumblr recently that had me clicking like on a lot of Role Player problems. http://role-player-problems.tumblr.com/
I've come up with my own from recent experiences in rping on ista.
"Roleplayer problem: making a cruel character who is called adorable and cute."
So, thought it would be fun if people added their own Role Player Problems, either from ista or maybe other places.