"And yet," Crowley pointed out. "You're still here." He tilted his head, looking at her. The hint of a challenge burned in his gaze. Either she'd stay, or she'd go. Either way, he knew he'd gotten to her. He always got to her, he just had that kind of effect on her.
His ultimate goal was not to make Anna more miserable. he'd put too much time and effort in to her, to want to watch her wallow. She had an inner strength that Crowley admired, except lately she wasn't pulling from it. She was letting herself get dragged down in to the trenches of humanity. Crowley sort of found that repulsive. By providing some level of normalcy, he hoped to drag her out of that sticky pit, and back where she belonged. It wasn't much fun for him to harass her, if she wasn't playing on his level.