Tonight we were treated to another installment of The Office After Dark. Nighttime episodes of The Office tend to rub a lot of fans the wrong way. They find them a little too kooky, dark and twisted. I, on the other hand, tend to dig them for those very same reasons. Accordingly, tonight's episode was big on boozy camaraderie, sordid confessions and psychodrama.
Yes, The Office gang was headed to Winnipeg! Dunder-Mifflin suit David Wallace decides to cheer up a despondent Michael Scott by sending him and wingmen Oscar and Andy to Canada for a sweet-ass business trip/really crappy vacation. Meanwhile, Jim patiently counts down the hours until Pam returns from art school and suffers the creepy smiles of his co-workers, all of whom disconcertingly seem as invested, if not more invested, in the happy couple's impending reunion than Jim himself, especially Creed, who subjects him to a seriously unnerving shoulder rub.
Michael beams with child-like enthusiasm before the trip, packing two suitcases just for souvenirs. Michael is the king of both self-delusion and small pleasures, so he treats the prospect of a mundane business trip like an all-expense paid cruise around the world. He's especially excited about the fact that his hotel has a concierge, a woman dedicated, in Michael's fevered imagination at least, to "fanciness and pleasure". Alas, he seems to have confused "concierge" with "concubine".
An ostensibly humbled Ryan decides to win Kelly back through an erotic display of his push-up prowess. Kelly proves an easy mark and it isn't long before they're engaged in a clumsy office hook-up. Ryan decides to make it easy for Kelly by thoughtfully composing her a text message breaking up with Darryl. "It's well written and all", Kelly concedes before they romantically hit the send button together.
Darryl couldn't be happier to finally be rid of Kelly and her craziness. In the episode's funniest moment he half-struts, half-swaggers to his car as if the biggest, most crushing weight in the world had just been lifted off his shoulders. It was a fucking genius sight gag, as was the look of abject mortification on Ryan's face once he realized that A. He wasn't fucking Darryl over so much as doing him a really big favor B. Breaking Kelly and Darryl up meant that he was now once again obligated to be the boyfriend of a needy, clinging, co-dependent flibbertigibbet
Be careful what you wish for indeed. Back in Winnipeg, Oscar and Andy get hammered on Long Island ice tea and it comes out that Andy hasn't had sex with Angela yet. When Andy drunkenly calls Angela and asks why they haven't hooked up yet he's demoted to first base–chastely kissing her forehead. Andy and Oscar really hit it off in Winnipeg–in a great talking head Andy beams that it's weird he had to travel to Canada to find out that Oscar is delightful!