One r/DunderMifflin thread ultimately pinpointed a scene in Season 4’s “Night Out” as the series’ single most cringe-worthy sequence. In the episode, most of the Dunder Mifflin employees end up accidentally locked inside the building for the night. Later, when Jim, Toby (Paul Lieberstein), and Pam laugh at a joke together, Toby unconsciously puts his hand on Pam’s knee, confirming his crush on her in front of everyone, including a mortified Jim. Toby climbs the fence and runs away but the sheer discomfort of his gesture stayed with the show’s viewers.
One Reddit user accurately commented that “Just the fact that it happens, everyone acknowledges it is happening, but no one does anything during this long awkward silence, that makes it so much worse.” Meanwhile, another Redditor observed that the “worst part of it is that Jim didn’t flick [Toby’s] skeezy hand off her leg.”
Other users in the thread also named “Phyllis’ Wedding,” where a jealous Michael nearly ruins the event, as well as Jan (Melora Hardin) singing “Son of a Preacher Man” at her baby shower; both truly hard to watch sequences in a show that thrived on them.
You can currently stream “Night Out” and other “Office” episodes on Peacock.