Hey, GAWAIN spends ridiculous amounts of time haunting HQ as well! Maybe these two have met often before, discussed the horrifying amounts of paperwork awaiting at their respective offices with the same tone the would speak of the weather?
Heck, considering they seem to both (least pretend to) posses amoral behavior, perhaps they've been dispatched in one or two or several Black Ops together since Dart joined?
GAWAIN I do like the idea of the two interacting in a more social setting. It's possible that they have worked together, and perhaps they are dealing with the after-action reports and such late one night at HQ?