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.
"This is a sixty-year MacCutcheon," says Widmore, taking two crystal glasses and going back to his desk as he blah-blahs about an Admiral MacCutcheon, the most decorated man in the Royal Navy, who retired to the highlands to spend his remaining years making whisky, and all of it is bullshit as far as I've been able to ascertain. Widmore sets the two glasses down on his desk, and Desmond allows himself a slight smile as he thinks this is a celebration. But with this much setup, and given what we already know, I think most of us were just waiting for the guillotine blade, hey? "Admiral MacCutcheon was a great man, Hume. This was his crowning achievement," says Widmore, and pours a little whisky into just one of the glasses, and puts the cap back on the bottle. Desmond's smile falters.
Widmore holds up the glass. "This swallow is worth more than you could make in a month," says Widmore. Because the pay in your administrative department is shit? Or... oh. A stricken Desmond watches as Widmore swallows the whisky, and looks reflectively at the glass before speaking again. "To share it with you would be a waste, and a disgrace to the great man who made it. Because you, Hume, will never be a great man."
It takes Desmond a while to answer, while Widmore's eyes burn holes through him. Holy shit, Desmond. Stand up for yourself! Part of me believes Widmore's testing him. But all Desmond can do is weakly stammer out, "I know I'm not... " and Widmore cuts him off. "What you're not, is worthy of drinking my whisky. How could you ever be worthy of my daughter?" Desmond just looks around and doesn't say anything. Not, "Too bad, we love each other," not "sod off," not anything. I'm having a really hard time rooting for Desmond when he seems so paralyzed by wussiness.
Outside, though, Desmond takes out his frustration on his tie, by angrily tearing it off and throwing it down on the sidewalk. Would it have killed him to have displayed a little bit of that fire in front of Widmore? Maybe, actually -- Widmore looks kind of tough.