The Office‘s Michael Scott is a complicated man. He can be sensitive, sweet, innocent, idiotic, and immature. Despite his silly antics, there’s plenty of evidence that he has a creepy side. Among the many strings to his bow, his creepiness is the most off-putting and difficult to watch.
One of the things Michael is less known for is displaying tact. Whether it’s adopting a creepy alter ego, attempting to kiss a co-worker, or just staring at someone, Michael has repeatedly revealed a side of him that can make others squirm, wince, and shudder.
9 Comparing Pam To A Previous Version Of Herself
In the pilot episode of The Office, Michael is introducing Pam to the camera. With a smarmy grin on his face, he says “If you think she’s cute now, you should have seen her a couple of years ago,” followed by a “rawrr.” Pam is taken aback and doesn’t know how to respond.
The scene perfectly conveyed what kind of person Michael Scott is, the kind that will not only make an inappropriate and degrading remark to someone’s face but will do so in front of a camera.
8 Being Inappropriate With Katy The Handbag Saleswoman
Michael Scott first meets Katy Moore in the episode Hot Girl. Katy sells handbags and briefly dates Jim. Michael compliments Katy, right in front of Pam, saying “Look at you, you’re like the new and improved Pam, Pam 6.0.”
He then latches on to the fact Katy likes drinking coffee and buys a coffee machine in the hopes of impressing her. When he asks about the coffee Katy had, he calls her a “greedy little thing.” Finally, Michael offers Katy a lift home, which she grudgingly accepts. Despite his creepiness, the viewer ends up feeling bad for Michael as Katy ditches Michael for Jim.
7 Getting Back With Jan Because She Had Breast Implants
Having sought the council of Pam, Angela, Phillis, and Karen Filippelli, Michael goes into his office where Jan is waiting, fully intending to break it off with her for good. What he doesn’t count on was the fact that Jan has had breast implants.
Clearly flummoxed, fans can see Michael thinking things over. In The Job, Michael is clearly trying to find a way to rationalize getting back together with Jan after declaring their relationship over. He decides to give her another chance because it’s “a sign of maturity.”
6 Attempting Proposes To Carol Before Trying To Kiss Pam At The Diwali Party
The episode Diwali isn’t one of Michael’s finest moments, even amongst the great number of embarrassing and creepy moments he’s had. Diwali starts with him proposing to Carol, with whom he’s gone on only nine dates. Understandably, Michael is rejected.
As Carol’s about to get into her car, Michael proposes that he comes with her because he’s got “this book called the Kama Sutra.” To top it off, a dejected Michael tries to kiss a similarly-dejected Pam, only to be rejected. He then asks for a ride home, to which Pam replies, “If you sit in the back.”
5 Saying He Has A Loaded Gun In His Desk
In Viewing Party, Michael is upset with Gabe because he thinks that the employees view Gabe as the boss and not him. During Gabe’s Glee-viewing party, the two fall out over the volume level of the TV and Michael stages his own viewing party in Gabe’s bedroom.
Pam enters and suggests he go back to the party. A lonely Michael sits on the bed and tells her with utmost seriousness that he has a loaded gun in his desk at work. He tells Pam that, if he ever acts like Gabe, she should shoot him 100 times in the groin until he’s dead.
4 Referring To A Photo Of Stanley’s Daughter Inappropriately
In Sexual Harassment, Michael thinks that the photo Stanley has put up on the wall next to his desk is from a magazine. Michael claims Stanley put it there because it’s “hot and sexy and turns him on.” Even if he didn’t realize the girl in the photo was Stanley’s daughter, it’s disgusting for Michael to declare that the best part of his morning is staring at a photo of someone who is quite clearly not an adult.
3 Kissing Oscar To Make A “Statement”
In what must surely be one of the most awkward scenes in The Office, Michael attempts to make a statement about homosexuality. Michael kisses Oscar in front of everyone during an office meeting in Gay Witch Hunt.
Oscar, not best pleased with his role in the scenario, fends Michael off and insults him. Oscar calls Michael small which makes Michael cry. Feeling guilty, Oscar then backtracks and allows Michael to plant a kiss on his nonreciprocal lips. Everyone in the room is at once confused, sad, and creeped out.
2 Staring Intensely At Ryan
Michael’s obsession with Ryan was perhaps best illustrated when he stared at him through the blinds from inside his office in episode 14 of season 2, The Carpet. With Pam on vacation, Ryan is manning the reception desk. This causes Ryan to be the subject of Jim’s glances, as Jim has become accustomed to looking over at Pam. Ryan isn’t as bothered by Jim’s habitual glances, as he is also in full view of Michael. The camera catches Michael staring at Ryan in a much more intense and creepy way.
1 Date Mike Unleashed An Onslaught Of Creepiness
In Happy Hour, Michael was having a perfectly good time with a woman in a bar until he found out that Pam had set him up on a date. Michael then creates and turns into a new alter ego, Date Mike. The vibe immediately turns sour as Date Mike unleashes an onslaught of forced, inappropriate behavior.
He attempts to tie a knot in the stem of a cherry and almost chokes, then knocks over a waitress’s tray with a pool cue, and does air guitar on a pool table. Date Mike’s date is horrified and he is threatened with being thrown out of the bar before he finally ditches the persona.
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