The Office Michael & Holly’s Most Awkward Moments

The Office: Michael & Holly’s Most Awkward Moments

Michael and Holly have a complicated love story. Here are the most awkward moments that occur throughout their tumultuous romance.

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Michael Scott has been through his fair share of heartbreak over the years. He was attached to Jan for far too, was willingly involved with a married woman, and even tried picking up waitresses at a Benihana. Michael can be desperate when he’s lonely but the moment he saw Holly he knew she was the one. And unlike many other times in his life, he turned out to be right about her.

Michael and Holly have a complicated love story. They were torn apart in different directions before finally coming together in Michael’s final season. However, even though they were engaged and in love, Holly and Michael had some of the most awkward encounters in Office history. To take a look at their strangest moments, scroll below!

10 When They Forgot To Lock The Office Doors After Sleeping Together In The Staircase

One of the most awkward moments between Holly and Michael is when they first slept together. Michael was nervous about moving to the next step with Holly and ended up blurting out the question (“Do you think we’re going to sleep together?”) while in the office.

Holly responded with “Hell yeah” before the two of them went back to work. Instead of going home to do the deed, however, Holly decided to make it official in the workspace. The only problem was that when they left the office, they forgot to lock the building. That night, someone broke into their office and stole important documentation because of Holly and Michael’s romp.

9 When Michael Sat On Holly’s Lap During A Meeting

Michael and Holly were beside themselves when they realized they loved each other so early on. Once they began dating, they couldn’t stop their acts of affection. Gabe even had to have a PDA meeting to get them to realize how uncomfortable they were making everyone.

In the PDA meeting, Michael sat on Holly’s lap because he loved the feeling of her thighs on his backside… The entire ordeal made the office uncomfortable and they didn’t understand why.

8 When They Took On Different Characters For Andy’s Business Meeting

When Andy is trying to become a better salesman, he creates a seminar in hopes of bringing in more business. To make sure everything went smoothly, Michael wanted to join the seminar as an actor, since the guests didn’t know who he was. However, Michael decided that he would be Greek.

Holly helped Michael perfect his Greek persona but Michael took it too far when he told her she was the love of his wife and tried kissing her. Holly and Michael weren’t dating at this point so she left in a hurry.

7 Their Disagreement Over What’s Ethical

With Holly as Dunder Mifflin’s human resource manager, it’s her job to make sure the office is running ethically. It’s obvious the Scranton branch is far from ethical but Holly tries hard to do her job.

At this point in the series, Holly and Michael were just friends, so when Michael’s ethics are different from Holly’s the two get into a disagreement in front of everyone. It gets worse when corporate sides with Michael.

6 When They Broke Up In Front Of Darryl

To avoid another Jan and Michael fiasco, David Wallace transferred Holly from Scranton to Nashua. They planned on making long-distance work but as they were driving they realized that they were never going to work. Holly begins crying in the car and Michael becomes concerned.

He awkwardly wonders why she’s crying and asks if it’s because Darryl touched her. She quickly says Darryl didn’t touch her and Darryl is mad at Michael for insinuating such a thing. Just another awkward day in the life of Michael and Holly.

5 When They Fought In The Middle Of The Office Over Woody

Only at Dunder Mifflin Scranton does a tiff between former loves involve the entire office.

With Holly back at the Scranton branch for a few months, Michael assumes they’ll start dating again, but the only problem is that Holly and AJ are still dating. Holly has a Woody doll on her desk and tells Michael it’s a gift from AJ. Michael, of course, didn’t handle it well and threw Woody in the trash at the Chrismas party and dumped his hot coffee on it. Holly found the doll and interrupted the party to find out who defaced her Woody doll. When Michael comes clean and brings up their relationship, Holly lets him down in front of everyone, which only made the entire office against her.

4 The Dreaded Company Picnic

As many awkward moments as Michael and Holly have, none were worse than their performance at the company picnic. Michael knew seeing Holly would mean a chance to rekindle their relationship but when she came holding hands with AJ, Michael changed his tactic.

He and Holly decided to team up for a performance for the entire company and it was an utter flop. They created their own version of Slum Dog Millionaire and changed the characters to match Dunder Mifflin’s history. Sadly, no one thought it was funny. Things got worse when Michael and Holly let the entire company picnic know that Dunder Mifflin was closing down the Buffalo branch… Unbeknownst to the Buffalo branch.

3 The Herpes Phone Call

When Michael wakes up with an ingrown hair above his lip, he assumes it’s a pimple. But when his co-workers tell him that a cold sore is related to herpes, he assumes he has herpes. Dwight forces Michael to call all his former lovers and tell them that he has herpes, which means they may have it too.

He calls all his former lovers, including Holly. The conversation didn’t go well, mainly because Michael couldn’t stop telling Holly that they’d probably be married with twins by now if she stayed in Scranton. Sadly for Michael, she turned him down and said he “romanticized” their relationship into something it wasn’t’.

2 When They Were Rubbing Hands In Front Of Oscar

When Holly finally gave into Michael the second time around and started dating him again, she couldn’t get enough. In fact, they both couldn’t. They barely left each other’s side the entire day.

When Oscar went into Michae’s office to ask him a question, Michael couldn’t focus on Oscar because he was too busy rubbing Holly’s hand. The two were oddly rubbing and rolling and tickling each other’s hand while simultaneously reading. It was awkward beyond measure.

1 When Michael Was Mean To Holly In Front Of Jan

In the early stages of their relationship, Holly and Michael became best friends, this is why she was stunned to find out that Michael had such a gorgeous ex-girlfriend (Jan) and that they were expecting a baby together. At Jan’s baby shower, Holly was—once again—disturbed that Michael was treating her so poorly.

She didn’t know who this new Michael was. He insulted her in front of the office just to make someone like Jan happy. It was incredibly awkward and humiliating for both Michael and Holly.

Link Source : https://screenrant.com/the-office-michael-scott-holly-awkward-moments/

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