10. Judy Collins Calls Out Hannah (Episode 8)
It'd be bad enough to have your high-school OCD rear its ugly head, as it did for Hannah. It would be worse still to fight with your parents about it. But to have OCD, fight with your parents about it and then have singer/songwriter/American treasure Judy Collins call you out from the stage as you slink toward the bathroom would be almost unbearably WTF.