Boss Man's Last Known Joke

The scene: our whole department is sitting in a conference room, trying to stay awake during a particularly boring meeting. And let me tell you, in order for one of our meetings to stick out in your memory because it was boring means that it was on a level of mundane thus far unbeknown to man. Add that to the fact that Boss Man had scheduled this particular meeting very, very close to Close of Business on a Friday, and you can see why the staff may have been a bit more perturbed at attending a boring meeting than usual.

And that leads me to say, with a small amount of sincerity: Thank God for Overshare.

Boss Man: And so... blah blah blah... blah blahtery blah.... and that should about wrap things up.
Group: [half of group wakes up, other half releases a collective relieved sigh]
Boss Man: Anyone else have anything they need to talk about or ask?
Group: [shoot Dagger Glares around the table, half-daring anyone to speak up and prolong the meeting]
Boss Man: No? Nothing?
New Colleague, Recently Relocated: I was just wondering... [group hastens to aim their Dagger Glares at her, she withers slightly] do we ever meet for dinners or anything, you know, off-site? To talk about strategy? Get to know each other?
Group: [grumbles]
Boss Man: Err... not really.
NC,RR: Oh. Well, maybe we should start.
Group: [collective sigh, everyone checks watches, rolls eyes]
Boss Man: Well... [decides a very, very rare attempt at a joke might break the tension] Overshare has a whole list of nightspots in her repertoire. Maybe she's willing to share.
Group: [Laughs nervously]
Overshare: I don't know what you're talking about, Boss Man!
Boss Man: I just thought that with your extensive social life...
Overshare, offended: I have no social life! I'm too busy keeping CTF out of jail!

Ok... how out of control does your Oversharing have to be for your BOSS to label your social life "extensive?" I would have died of embarrassment, and that Keeping My Boyfriend Out of Jail excuse? Yeah, I would have kept that to myself.