My 10 Favorite Awkward Moments From The Office
10 — Michael’s Diary Is Revealed During A Deposition
During Jan’s lawsuit against Dunder-Mifflin, she enters into evidence, Michael’s personal diary. Copies are made for everyone involved in the case and passed out to be thoroughly examined during the deposition. Michael’s in-office nemesis and Scranton’s human resources rep Toby also gets his hands on one.
9 — Jim’s New Boss Is Not Amused
When Dwight sends out a memo that office workers are dressing too informally, Jim shows up the next day in a full tuxedo. Unfortunately for him, that day is also the day their new boss drops by to observe the office and he is not humored by Jim’s prank.
8 — Ryan Asks to Take the Lead
Ryan and Stanley are sent on a sales call together and on the way, an over-zealous Ryan asks to take the lead during the presentation to one of Stanley’s regular clients. Stanley humorously agrees and enjoys himself perhaps a bit too much as Ryan makes the pitch to a group comprised completely of distinguished black businessmen.
7 — Michael Presses Send All
Michael went on a tropical getaway with his boss/girlfriend, which resulted in Michael gaining possession of erotic pictures of his partner. When attempting to email the pictures to a longtime frat-buddy friend, Michael accidentally hits “send all” and emails the entire company list serve.
6 — Dwight Tells Holly that Kevin is Mentally Challenged
When the office gets a new human resources representative following Toby’s departure for Costa Rica, Dwight informs Holly that Kevin is mentally challenged. She goes to bat for Kevin several times, criticizing the other office workers for berating him and helping him with simple tasks until Kevin reveals to her that he is not mentally challenged.
5 — Michael Enjoys a Picture of Stanley’s Daughter
While lecturing the office about what is and is not appropriate in the workplace, he references the photo of an attractive young black girl in a Catholic schoolgirl that Stanley keeps at his desk. The girl is, in fact, Stanley’s underage daughter that attends Catholic girls school.
4 — Pam Walks In on Michael Changing
Michael calls Pam into his office to discuss something reception-related, but she arrives quicker than he anticipated. When she knocks on the door, Michael ushers her in while still pulling up his pants and underwear. He loses his balance as she comes in and his drawers fall down, leaving Michael quite exposed and bottomless.
3 — Pam breast-feeds the wrong baby
After Pam gives birth to CeCe, she struggles to breastfeed her firstborn. The newborn does not seem anxious to latch on and Jim and Pam spend several awkward sessions with a breast-feeding instructor. A few nights after the birth, Pam successfully feeds their baby, only to realize after the feeding that the baby that just chowed down belonged to the couple sharing their room.
2 — Michael kisses Oscar
Oscar is unintentionally outed by Michael and Dwight which leaves Michael attempting to prove he is completely accepting of Oscar’s lifestyle. By the end of the episode and after several offensive shenanigans, Michael calls a staff meeting in the conference room which culminates in Michael kissing a very disturbed Oscar on the mouth.
1 — Michael reneges on a promise
Ten years previously, Michael had made an arrangement with 20 young children. He promised that if they graduated from high school, then he would pay for their college education. Scott’s Tots approach their graduation day and throw a celebratory party to thank Michael. But Michael’s knack for exaggeration forces him renege on his promise. He sits through the entire performance and accepts their gratitudes before telling them he can’t afford to put them all through school. He does however, buy all of them batteries for a laptop.