Awkward Conversations: You Tell Your Boss You Have A Dentist Appointment During The NCAAs
March 18th, 2008 by NextRound
[You knock on your boss’s door. He waves you in.]
You: Morning, boss. Gotta second for me to run something by you?
Your Boss: Sure, take a seat. What’s up?
You: Well, let me first say I’m a complete idiot for not bringing this up before now. But I’ve got this upcoming root canal scheduled. Think I’ve been working so hard I just blanked on it. I would have forgotten altogether if an Outlook reminder hadn’t just popped up. God bless Office 2003.
Your Boss: OK, not too big a deal. When is it?
You: It’s scheduled for this Thursday and Friday.
[Five seconds go by as he looks at you like he’s trying to figure out if you just farted.]
Your Boss: This Thursday and Friday?
You: Yeah. I think it’s two days because it’s such an important procedure. Luckily it’s only in the afternoons. Although I may not even be able to come in Friday morning because of the pain in my face. I’ll try to tough it out, of course. You know me, I’m a trooper.
Your Boss: It’s this Thursday and Friday, and only in the afternoon?
You: Yeah, I thought that was weird too. But hey, you can’t argue with doctors can you? The asshole probably has tee times both mornings and I’m the one whose schedule gets screwed.
Your Boss: So this two day dentist appointment…
You: Root canal, actually, sir. A lot more serious.
Your Boss: Oh, yeah, thanks for the clarification. “Root canal”. Sooooo, what you’re telling me is you have a two day “root canal”, only in the afternoons, and this root canal just happens to coincide with the first two rounds of the NCAA tournament.
[You do your best imitation of the who farted face right back at him.]
You: Huh? Sir, I’m going to have to apologize for my ignorance here, but I’m a little confused. What could my root canal possibly have to do with the NCAA tournament?
Your Boss: You’re saying there’s no correlation?
You: How could there be? One is an extensive medical procedure, something many people consider a serious surgery. I think I read somewhere where the mortality rate is up to about 10%. And the other is…what? A sporting event, right? I believe it’s basketball. Or is it baseball?
Your Boss: You don’t know what sport it is?
You: Well, I think it’s basketball. I saw a poster in the Children’s hospital I volunteer at that led to me believe it’s basketball. But I’m not a big sports guy. Unless you consider loving your work a sport. Then I’m a MASSIVE sports guy.
Your Boss: Didn’t I see you and Johnson comparing your brackets yesterday?
You: I think you must be mistaken sir. The only brackets I use are for carpentry. Like Jesus.
Your Boss: No, I’m pretty sure it was you and Johnson. I remember because I overheard you telling him–and I’m paraphrasing here–that he was a “big fucking homer for putting Indiana in the Elite Eight” and how he “might as well go ahead and give you the money he was planning to use to buy a hooker this weekend, because it will be yours soon enough.”
You: Ummmm…Wow. Sir, no disrespect, but that sure doesn’t sound like me. The profanity, the sports knowledge, the reference to prostitution. Not like me at all. Are you sure Johnson wasn’t talking to himself? He’s kind of a weird dude.
Your Boss: No. I specifically remember listening to you tell him “he’s about as good at picking winners as he is at picking out chicks that don’t look like guys.” And it really stuck with me because his date to the Christmas party had more hair on her arms than I do.
You: Again, sir, I think there may be some sort of confusion…
Your Boss: OK, well do you have a note from your dentist?
You: A note? Ha. What is this middle school? Do I need to start getting hall passes from you to take a dump?
Your Boss: Well, can I give your dentist a call then? Sounds like this is a pretty serious procedure. I probably need to make sure there aren’t any special accommodations you’ll need around here.
You: Oh, funny you mention that, because it’s actually the oral surgeon doing the procedure. The referring dentist is vacationing at his timeshare in Boca…
Your Boss: Geezus. You are seriously full of shit. Listen, I’m not doing dick for work around here on Thursday or Friday either. Let’s plan on heading out at 11 to make sure we get a good seat at the bar. You have to buy the first beer for being an asshole, though.
[You start easing your way out of his office.]
You: Uh, OK. 11 it is. I’ll have to reschedule that root canal, but for you boss…
Your Boss: Make sure you bring ones. Where we’re watching the game, you’ll need them. Hope you like lunch buffets.
Previous Editions of Awkward Conversations:
“Awkward Conversations” is the segment where NextRound makes up exchanges between famous and quasi-famous people. Click here for previous editions.

















