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The Office: The 10 Cringiest Michael Scott Moments That Make Us Want To Crawl Out Of Our Skin

While it's been almost six years, the American version of The Office has remained one of the most endearing TV comedies of the late 2000s and early aughts. A lot of that is thanks to Steve Carell's portrayal of the insanely inappropriate regional manager of Dunder Mifflin, Michael Scott. Sure, he departed from the series in season seven, but he left some truly wince-worthy memories that we just can't erase. That's why we watch, however, so if you're looking to watch some awkward comedy on Netflix, we've listed the cringiest Michael Scott moments from The Office.

RELATED: Ranked: The Office's Funniest Characters

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10 Date Mike

From: "Happy Hour" (Season 6, Episode 21)

Oh God, this one hurts to watch. Pam Beasley (Jenna Fischer) and Jim Halpert (John Krasinski) invite a friend to meet Michael at an office happy hour event in the hopes they can spark romance. At first, it goes well, then he realizes he's on a date. So despite things going smoothly, our favorite regional manager runs to his car, grabs a cap from his trunk, undoes a few buttons, and comes back as "Date Mike". Everything about this is all kinds of cringe and he almost gets kicked out of the bar. To make matters worse, he ends up ditching his date for another person!

9 Kissing Oscar

From: "Gay Witch Hunt" (Season 3, Episode 1)

In an attempt to help Oscar Martinez (Oscar Nunez) come out as gay, Michael holds a meeting for him against his wishes. In an attempt to help the office get a little more accepting, Michael then offers to hug the accountant. Oscar says he doesn't want to, but then does, and then Michael goes in for a kiss. This is really hard to watch but in the best way.

8 The Dinner Party Fight

From: "Dinner Party" (Season 4, Episode 9)

Jan Levinson (Melora Hardin) and Michael Scott had one dysfunctional relationship, and it all came crashing down in one awful dinner party. While waiting for dinner to be served at 11:00 p.m., the two started throwing passive-aggressive jabs at each other in front of Pam, Jim, Dwight Schrute (Rainn Wilson), Andy Benard (Ed Helms), and Angela Martin (Angela Kinsey). The two argued about everything — including getting and reversing a number of vasectomies — but came to a head when Jan threw one of Michael's Dundee awards at his tiny $200 plasma screen TV.

We've all been out with a fighting couple before, so this episode, while exaggerated, is just a tad bit too relatable.

7 Michael's Diary

From: "The Deposition"(Season 4, Episode 12)

Michael Scott had to make a tough decision when Jan decided to take legal action against Dunder Mifflin for her dismissal, and Michael Scott is the person the whole case hinges on. Despite that, he made some poorly timed jokes and tried to weasel out of a few questions but the worst of it occurred when his diary was read to the room.

In the pages, he detailed how he slept with his boss Jan, how she said it was a mistake and spoke a lot about how attractive he thinks Ryan Howard (B.J. Novak) is.

Even his David Wallice, Dunder Mifflin's Chief Financial Officer, apologizes when it's all said and done. To make matters even more awkward, he ends up taking the company's side in the entire ordeal and has to drive back home with Jan after missing out on a $4 million payout.

6 Forgetting Who His Girlfriend Is

From: "A Benihana Christmas" (Season 3 Episode 10 & 11)

Michael Scott had a really bad Christmas in 2006. Following the end to a short but intense, relationship, Michael is down in the dumps and is taken out for lunch at a Japanese restaurant prior to the Office's holiday party. There he meets a waitress and he takes her back to the event along with her friend who came with Andy. Now, the fact that they seem way too young, to begin with, is cringy enough, but it gets worse. Unfortunately, Michael gets a little too tipsy and can't tell the two apart. So, to differentiate the two, he marks the one that came with him when he goes in for a hug.

5 Replacing His Girlfriend's Ex-Husband In Family Vacation Photo

From: "A Benihana Christmas" (Season 3 Episode 10)

Michael Scott is a bold man. So bold, in fact, that he literally photoshopped his face of his girlfriend's ex-husband in a family vacation photo with her kids.

Related: The Office: 10 Times Jim Halpert Was Actually A Jerk

Obviously, he got called out on it, but to try and cheer her up, he invites her on a trip to Sandbanks, Jamacia. Obviously, she breaks up with him, but man, what an awful car wreck to witness.

4 His Appearance On TV

From: "Take Your Daughter To Work Day" (Season 2 Episode 18)

Michael Scott was something of a child star back in the day. OK, well he appeared on a children's show and somehow was just as awkward as his adult self. When asked what he wants when he grows up, he replies by saying he desires a family with many kids so that he can have friends who will never leave him.

This is compounded by the fact that, at that point in time, Scott was single, hitting 40, and didn't have any children.

3 Helping Tony Gardner On The Table

From: "The Merger" (Season 3, Episode 8)

When Dunder Mifflin Scranton absorbed the Stamford, Connecticut branch, a lot of the talent coming to Pennsylvania were a little uneasy about the transition. So, to ease the new blood's fears, Michael Scott puts together a party where he puts the new members of the branch on a pedestal — literally. Moving a table in the conference room to a wall, he placed a few chairs on top and welcomed the Connecticut team to take a seat on their thrones. The only issue was, one of them, Tony Gardiner, was a little too large to do so.

Instead of respecting his employee's wishes and letting him stand away from the table, Michael forced the issue and even tried lifting him up to help him. After a few seconds of awkward groaning and groping, Tony yells at Michael and quits. To assert his dominance, however, Michael fires the upset employee, which means the company then has to give him a severance package. Yikes.

2 Walking Phyllis' Father's Wheelchair Down The Aisle

From: "Phyllis' Wedding" (Season 3, Episode 16)

To get a bit of a longer honeymoon, Phyllis Vance (Phyllis Smith) allows Michael to push her wheelchair-bound father down the aisle — a move she probably regrets.

Michael is quite the hassle the entire day, but when it came down to doing his actual job, he's not needed. Phyllis' dad gets up and slowly makes his way with his daughter, getting an ovation when he does. Not to be upstaged, Michael Scott still walks towards the altar, dragging the wheelchair as he does. Then, he squeezes himself in between two groomsmen who didn't want him up there.

After shoving his way between everyone, the ceremony proceeds, and when the priest says "you may kiss the bride" Michael yells "Ladies and gentlemen, may I present to you for the first time as a couple, Mr. and Mrs. Bob Vance!" to a silent chapel. That's because the couple didn't kiss yet.

1 Scott's Tots Get Batteries Instead Of College Tuition

From: "Scott's Tots" (Season 6, Episode 12)

Thinking he will be a millionaire by the time he's 40, Michael promises a group of inner-city third-graders that he will pay their college tuition if they can keep up good enough grades to get into university. Yet, his roadmap of the future didn't really pan out. 10 years later, he was invited to a thank-you event — which featured some inspiring speeches and an entertaining musical number — from the graduating class, he had to tell them all he couldn't afford their tuition. To make up for it, however, The Regional Manager of Dunder Mifflin Scranton offered the kids some laptop batteries.

It's simultaneously the best and worst The Office has ever been, and we still can't watch this episode without covering our faces out of second-hand embarrassment.

Next: 10 Times Creed Was The Best Character On The Office

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