A two-part question.

Part one: If your new boss looks exactly like Conan O’Brien, at what point is it appropriate to tell him?

Things to consider: Lack of knowledge about his sense of humor; Halloween costumes; possibly unleashing a wild torrent of humor that may completely dishevel the entire office; the fact that he might already know this and be either very proud of this, or very annoyed by it; the liklihood that if you wait it out and get to know him better, he won’t really look like Conan anymore; live late-night entertainment; a tabloid scoop about Conan’s “day job.”  

Part two: What is the most appropriate way to express this pent-up fact?
A. Throw it into the conversation. “Sure, I can get that done by Thursday good show last night and I will get those photos assigned, too.”
B. Via e-mail, such as “Hey Conan, so here are those TPS reports…”
C. Via e-card, such as one that says, “You look exactly like Conan.” I crafted a brilliant one on someecards.com but they have that site fancied up so I can’t figure out how to post it here.
D. Casually send him this blog. If he doesn’t think it’s funny, be like, “What? Gosh, wait, what, oh you thought I was talking YOU? Oh my gosh, NOOOO, of course not, gee. I was talking about … my friend told me she has this boss who… ha, yeah, funny that you would even think I meant you, because, duh, obviously, you don’t at all, you’re totally more like David Letterman…? NO, I mean Jay… no? No. You’re right. I should go home now.”

I think I’m going with D.
Wish me and my holiday bonus (or soon-to-be retracted bonus) luck.

And on that note, let it be known that I think Conan is REALLY, REALLY GOOD LOOKING, but in a completely professional and respectable way.

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