Your boss tells you says, "You look ... Tired."
I sure hope so!
I think you may be interpreting that phrasing differently than it was intended. :)
As the person who wrote this, thinking about the daring response makes me want to cry. Or be sick. Or both.
I'd probably say "I am, thank you for noticing," then go on to explain, "it's been rough. One of the guys was up all night, and started yelling around 3:00 AM."
This is why Tony is self employed.
Crazy response: "You look like Mr. Burns. But I can take a nap."
Daring response: "You look like you've been working me too hard."
Smart response: "Maybe a little. There's just so much to do!"