Define "creepy" .

1) Ever paid for a staffer/lover's abortion?

2) Any "parties" involving more than one consensual participant/staffer?

3) Any "quid pro quo" involved? (meaning a raise/promotion that came thanks to sexual favors performed?)

4) Any major age differences, or particular staffer "types" that were preferred (ie/early 20s/blondes/perky)? Any signs of "recruiting" such types to work for the show who later might be asked to date the boss?

I think that last question is really the one that will be focused on as the names, backgrounds of these women surely will be leaked by the media.

Did Letterman have good taste in his women? If so, I suspect he gets a pass. If they seem smart, independent, and decently good looking, then I think the public judges him differently than if these women are more of an easier type (ie/ the "bimbo" who solely serves as sexual outlet).

If Letterman expects addressing this in advance for a home-team audience willing to laugh it up will end the questions, I doubt it. The media loves a sex scandal, and the politically correct world has long been suspicious of employment relationships -- that's why you generally re-assign people to avoid the appearance of a conflict of interest if people at work start to date.

If, say, he paid for an abortion to cover irresponsibility... If it turns out there were no real dating "relationships", just sex hookups one after another... If any workers were given preferential treatment for sleeping with the boss...

It's all going to come down to how you define "creepy", I suspect.