Desmond sits in Widmore's office while the old bastard himself looks over Desmond's rÃ©sumÃ©. Des occupies himself by examining a painting with a polar bear, mountains, a Buddha, and "etsaman" (read it backwards) on it all muddled together, very hatch-mural-esque.
"Penny didn't tell me you were an actor, Desmond," says Widmore, glancing up, and Desmond says he was actually a set designer for the Royal Shakespeare Company. "Impressive," says Widmore, although I assume he thinks it's anything but. Also not actually impressive to Widmore is the fact Desmond didn't graduate from university. "No, sir. I had to look after my three brothers after my father--" begins Desmond, but Widmore interrupts him to ask if he has any military experience. "No, sir," says Desmond, clearly understanding that this isn't going very well. Widmore goes back to glaring at Desmond's resumÃ©, and Desmond looks around the office, settling on a model boat, which he says is beautiful. "My foundation is sponsoring a solo race around the world," says Widmore, and we see some more flashes: Desmond's boat in the stormy weather, the boat in the cove, and a dead, bloody Clancy Motherfucking Brown. "Something wrong?" asks Widmore, and Desmond says there isn't.
Somewhat to my surprise, Widmore offers Desmond a job in the administrative department. "Not the most glamorous duty, but it's a start. I'll speak to human resources." And what passes for a smile even crosses the old bastard's lips. But Desmond says, "With all due respect, sir, I haven't come here to interview for a position in your company." "You haven't?" says Widmore. The glare is back. Desmond says he's come to ask for Penny's hand in marriage. "We've been together two years now, and Pen's moving in and I love her. Your permission would mean everything to me." In hindsight, Desmond might have opened with asking for Widmore's blessing, instead of letting the old bastard look over Des's apparently rather unremarkable rÃ©sumÃ©, especially as he was going to turn down the job offer anyway.
Nevertheless, Widmore says he's impressed, and even it looks, and calls it a "noble gesture" as he gets up and walks over to the liquor cabinet (god, I want an office with a liquor cabinet) and asks if Desmond knows anything about whisky. I think if a potential father-in-law asks you that question, you need to be really careful about your answer. For example, "What don't I know about whisky!" is not the right answer. Desmond says he doesn't know anything, and Widmore picks up a bottle of the same stuff Charlie, Hurley and Desmond will be drinking on the beach in a few years.