Me: "Roll persuasion to seduce the guild member into giving you a discount on house repairs"

My bard: "This is where I get a Nat 1, guys."

*Gets a Nat 1. Everyone Laughs*

Yes harr de harr, she jinxed herself, but her attitude going into that roll is what worries me; Self-defeating, and with a chip her shoulder.

I'm running out of ideas to assist this player who, despite playing with us for +3 years, does not seem to TRY to understand what she can and can't do in her given role, and clearly just wants to "exist" in the game with us, her friends, who are too tight of unit to ask her to leave.

I don't know how to design an encounter that is going to be "fun" or "challenging" for my seasoned wizard player, but that is just going to completely shut down my Bard player.