Which episode of The Office is the most awkward of all time? 'Scott's Tots' vs. 'The Dinner Party'

It’s not easy determining the most cringeworthy episode of The Office, but EW TV critics Kristen Baldwin and Darren Franich were up to the task. Read on as they take sides over which Michael Scott situation is hardest to watch.

KRISTEN: When it comes to cringe comedy, Darren, The Office is television’s undisputed champion. But we’re here to debate which Office episode is more wince-inducing: the agonizing “Dinner Party” (season 4) or the literally dreadful “Scott’s Tots” (season 6). While it’s impossible to get through either one without suffering severe secondhand embarrassment, my vote for Most Hilariously Painful Office episode goes to “Scott’s Tots,” in which Michael Scott’s boneheaded promise to put 15 students through college comes back to bite him after 10 years. When the bill finally comes due, Stanley can’t stop cackling with schadenfreude-y glee now that Michael has to tell the kids the truth, but it’s Pam who speaks for the rest of us: “Michael, this is a terrible, terrible thing you’ve done…. The longer you put it off, the worse it’s gonna get.” And, Darren, it gets worse. So much worse.

DARREN: Disturbing indeed, Kristen, to see the collective ruination of youthful hopes for the future. But Jean-Paul Sartre said that “hell is other people.” I assume that quote comes from Sartre’s recap of “Dinner Party.” Michael entraps Jim and Pam into an at-home group couples date, which becomes a mesmerizing showcase of relationship dysfunction.

All hail Melora Hardin as Jan, the onetime Dunder Mifflin executive turned candlemaker and live-in girlfriend, who makes every cheerful line sound dangerously acidic. It becomes a running terror joke how often Jan and Michael say “Babe?” to each other, and even a casual game of charades turns into a ticking time bomb of pent-up hostility. I got nervous whenever The Office left the office, but this misadventure conjures the particular awkwardness of socializing with people you badly don’t want to socialize with. And the vasectomies, Kristen, the vasectomies!

KRISTEN: I’m cringing even just reading about “Dinner Party,” Darren. And indeed, that episode is 22 minutes of intense awkwardness, but what I think makes “Scott’s Tots” even more painful is how long it delays the inevitable — in this case, Michael Scott’s demoralizing destruction of a group of young graduates’ dreams. Because before he can tell them the awful truth — he doesn’t have, and never did have, enough money to send these kids to college — Michael (and we) are forced to watch as the bright young students (all wearing “Scott’s Tots” T-shirts) sing his praises, literally, with a special rap-and-dance number written just for him. (“Hey, Mr. Scott! Whatcha gonna do? Whatcha gonna do/ Make our dreams come true!”)

But that’s not all! Another student testifies that Michael’s promise kept him out of the “drug game” and a teacher gives an emotional tribute to the Dunder Mifflin doofus, saying his generosity proves that “anything is possible.” By the time Michael finally (finally!) stands up in front of his “Tots” and comes clean — followed by a whispered, “I’m so, so sorry” — I was curled up on my couch in the fetal position. No more! I can’t take it!

DARREN: You’re so right about the sustained anxiety, how the truth is a loaded gun waiting to go off in Michael’s face. “Dinner Party” similarly circles the drain of a very simple revelation: Michael and Jan hate each other. By this point in the show’s run, The Office was full of dating coworkers — Andy and Angela also attend, to Dwight’s chagrin — and I love how this episode defenestrates the very idea of a will-they/won’t-they romance. “I can’t prove it,” Michael whispers, “but I think she might be trying to poison me.” They’re poisoning each other emotionally, and we watch their corrosion play out like horrifically personal dinner theater. Except there’s no dinner, Kristen, because Jan’s osso bucco needs three hours to braise. Thankfully, “Dinner Party” runs only 22 minutes, just long enough to cook this bad romance’s goose.

To check out the runners-up, grab a copy of Entertainment Weekly’s Ultimate Guide to The Office, available now wherever magazines are sold or buy it online.

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