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The Most Awkward, Impossible To Watch Episodes Of 'The Office' Because Of Michael  

Jacob Shelton
1.8k votes 355 voters 8.6k views 14 items

List Rules Vote up the episodes of 'The Office' you can barely watch because Michael is so excruciatingly awkward.

The Office is built on watching its cast live through painfully embarrassing moments, and no character better personifies the series' uncomfortable underpinnings than Michael Scott. Across his seven seasons on the show, Michael proves himself inept, quick to anger, kind of dumb, and just all around awful. Somehow, he embodies all these negative traits while still having a heart of gold.

In the most awkward Office episodes, however, Michael leans into his worst qualities without ever trying to redeem himself. While funny, these moments don’t offer viewers a sense of narrative atonement; it just looks like Michael is a bad person. Thankfully, Michael is played by Steve Carell, who loads the character with enough sweetness to make you want to binge the show until you pass out - but you may be passing out from rage.

1 175 VOTES
Phyllis’ Wedding (Season 3, Episode 15)
Phyllis’ Wedding (Season 3, Ep... is listed (or ranked) 1 on the list The Most Awkward, Impossible To Watch Episodes Of 'The Office' Because Of Michael
Photo: Universal Pictures Home Entertainment

It’s always a wedding or a party that brings out Michael Scott’s urgent need for attention. Throughout the episode, he impedes on Phyllis’s ceremony; he’s then thrown out of the reception by Bob Vance for giving a truly horrific toast.

Michael’s behavior is so abhorrent even Dwight won’t let him back in the wedding. Unfortunately, this isn’t the last wedding Michael ruins.

Is this horrifically awkward?
Gay Witch Hunt is listed (or ranked) 2 on the list The Most Awkward, Impossible To Watch Episodes Of 'The Office' Because Of Michael
Photo: Universal Pictures Home Entertainment

Not only does Michael unintentionally out Oscar as being gay in this episode, but he does so by using a bigoted epithet. Throughout the episode, his ignorance will shake you to your core, but that’s hardly the most uncomfortable part of the show.

While apologizing to Oscar in an office-wide meeting (where else?), Michael kisses him without his consent - then Dwight tries to follow suit.

Is this horrifically awkward?
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3 149 VOTES
Double Date (Season 6, Episode 9)
Double Date (Season 6, Episode... is listed (or ranked) 3 on the list The Most Awkward, Impossible To Watch Episodes Of 'The Office' Because Of Michael
Photo: Universal Pictures Home Entertainment

After dating Pam’s mom for a few episodes, Michael books a reservation at a restaurant Pam loves for a double date with her and Jim to celebrate her mother’s birthday. While on the date, Michael realizes that at the age of 58, Pam’s mom doesn’t share his same interests - specifically, traveling and “white water rafting.”

Michael breaks up with her right there, ensuring no one in Pam’s family will ever forget her mother’s birthday.

Is this horrifically awkward?
4 125 VOTES
Happy Hour (Season 6, Episode 21)
Happy Hour (Season 6, Episode ... is listed (or ranked) 4 on the list The Most Awkward, Impossible To Watch Episodes Of 'The Office' Because Of Michael
Photo: Universal Pictures Home Entertainment

When the whole office goes out for happy hour, Pam invites her friend Julie along to meet Michael. After Michael and Julie hit it off, he changes from the laidback, fun Michael into “Date Mike,” who’s awful to be around.

Wearing a Kangol hat and an open shirt, “Date Mike” acts on his most misguided instincts and leans into being the worst version of himself. He ruins pool games and, at one point, tries to tie a knot in a cherry stem with his tongue - and chokes on it.

Michael almost gets kicked out of the bar by the manager, yet somehow he lands a date with her.

Is this horrifically awkward?