There's a soft smile audible in his reply. "Good night, Pepper." He thinks he likes being on a first name basis with her, though he can't explain why such a simple thing gets under his skin. He tries desperately to call upon the drowsiness he'd felt lying on the mat in the gym not too long ago. But now it's predictably gone. He's alone in the dark with his thoughts and that never helps him accomplish much at the end of it all.

For an hour or so, Tony actively tries to follow her into sleep, but then he's turning over in frustration, staring at the ceiling for a few seconds before his curiosity gets the better of him. He moves as subtly as he can onto his side facing her, the blue tendrils of light that escape through his shirt framing her peaceful countenance perfectly. He can't say for sure why, but laying there next to her and observing her sleep helps him relax. Watching her for another hour at least he's eventually able to drift off, face only a half-pillow's space from hers.