What was Michael's most awkward, cringe-inducing moment? Needless to say, there have been many! For me, the worst one was when he showed up at Jim's party uninvited. No matter how many times I've seen it I can't help but cringe after Dwight yells "surprise!".

"I was just driving by, figured I'd stop in."
To Ryan: "Temp - take my coat!"
To the middle-eastern IT guy: "come on, THAT guy?!?"
To the camera immediately after: "he's a good guy. Not a terrorist."

Ouch.

Hiding behind the mop as Jan is telling the warehouse guys that the plant would be closed if they formed a union.
"If you have any further questions you can direct them to Michael"

The Diversity workshop -- with everyone wearing index cards on their foreheads -- was a very special Michael moment.

Anything with Jan. It was pretty good when his two dates met at Casino night and he was trying to defend himself.

Yeah, or in Valentines Day when he blurts out in front of all the other branch managers that Jan is (or used to be) his girlfriend. Ouch!

How about in The Injury when Michael was putting the owner of the building under the spotlight because he is in a wheelchair:

Michael: "How long does it take you to brush your teeth in the morning?"

Good one! I think it's right after that that Jim says to the camera that he'd like to clamp Michael's FACE in a George Foreman grill!

End of Health Care when Michael comes back with ice cream sandwiches and Stanley says "that's not the surprise is it?
Michael: "No, of course not.
Then the entire office stands around at the end of the day waiting for the surprise, which, of course, there isn't any.
Hard to watch Michael try to think of something to say.

I need clean urine... for the lady.

enough said?

Agreed...doing drugs & then lying about it isn't very Michaelish.

Anything in "Sexual Harassment"

When he makes his online dating name "little kid lover"

"The only thing I'm worried about is getting a boner"

"I'll have the chicken breast...hold the chicken" to the Hooters waitress.

Jim's expression says it all!

Also, he looked like such a spaz in the whole improv scene.

Give me all your guns!

These are all so good! Here's another:
During "The Fire" and the game of "who'd you do?"
"I play this game all the time before I go to sleep!"
and, of course...
"Well, I would definitely have sex with Ryan, because he's going to own his own business."

The whole suggestion box scene in the conference room during Performance Evaluation just makes me cringe every time I see it.

Also, during Casino Night, when Darryl is in Michael's office and Dwight says Michael asked him to come in when Darryl arrived "for protection."

OMG.

"I said not THAT." Priceless.

The worst was the pilot when he pretended to fire Pam and made her cry. He looks SO uncomfortable w/ Ryan there just shaking his head.

You are so right!! It was such an awful situation.

Sadly, I think Michael's most awkward moment was his kiss with Jan in The Client.... If you watch it, you'll see that he goes in and just holds his head completely still, like he has no friggin' clue what he's supposed to do after that. Jan gets the action going (yeah, she must have been REAL drunk) but Steve Carell does such an awesome job in a 40-year-old-virgin kind of way!

Oh! This is fun!!

Okay, I would say the best awkward Michael moment was when he opened up his secret santa gift and got a homemade cheap oven mitt after he had spent over $300 on his gift. Not an "even" exchange. hahahaha!

During "Take your Daughter..." when he shows the television segment that he was on as a little boy - everything about that scene is profoundly awkward.

That scene just about broke my heart. And then Toby's daughter says, "so you didn't get to be what you wanted to be."
How awkward was it when Michael was asking Toby if Sasha (I think that's her name) had a godfather?

When he imitates a Hindu convenience store owner and tries to sell googy-googy to Kelly....
When he talks smack about Tobey to Katy, in front of Tobey!
When he answers the call from Todd Packer and T.P. asks that impertinent question about Jan's physique....
When Craig discloses Michael and Jan's affair during the staff meeting at corporate headquarters.
Is that enough? Shall I continue?

From Casino Night when he is about to roll the dice (di? I don't know how to make that plural. I feel like Michael, it's incalcalable)...
Anyway- He has Carol blow and then says he's not playing favorites and puts them in front of Jan's face. Right in front of everyone!

Also when he goes to buy the condo and he meets the Homeowner's Association guy, Bill. He starts quoting the old SNL skits and no one has any clue what he's talking about- or if they do it's just not funny.

When he goes to get a "great joke" from the warehouse guys and they just start making fun of him in Sexual Harrassment. That was just sad. Yeah, whoever said the entire episode was right.

FYI
Dice is plural - die is singular
"it is so sad that I know that"

Here's one: In "Basketball" when Phyllis offers to be a cheerleader and Michael just blurts out "Ewww, gross!" and then tries to cover himself. Michael trying to cover his screw ups is as entertaining as the screw ups themselves, in my opinion.

Also, i have to mention Michael stretching out the drum roll in "Healthcare" and then just has NOTHING for a surprise. I know it's been mentioned, but there's nothing that says two people can't have the same moment, so...

Yeah, and then they start walking out and he's just standing there with nothing to say. Brutal!

I also should mention the scene in the Fire where Michael and Ryan are in the car. Michael asks Ryan what he thinks and Ryan suggests getting some air because he's miserably uncomfortable. Michael says he's fine and then Ryan, with [censored] i might add, just flat out says, "I'm really uncomfortable." It's so great.

Um, hello. On the booze cruise when he repeats all of the safety instructions that Capitan jack says. "I am your party capt. Too!" That one pains me. PLus at the end when he tells everyone that the boat is sinking. Slay me.

in the fight

michael: queer... eye. that is a good show. important show. yeah

this thread is great

what about when Michael gets hit in the face on accident while playing basketball in the warehouse and then ends the entire game saying that it was a "damn shame" about them playing that way....

Thank you jimrox. Obviously I only have street smarts... and book smarts.

In line with the queer eye thing, how about when he calls Jim gay? In the bad at sports way, I think that goes without saying.

I have to say, looking back over these awkward moments, that this one takes the cake. I saw it coming and I still couldn't get out of the way. I think I hid my face in my hands for most of this scene.

We all know that Michael Scott(steve carell) is the reason why The Office is so funny because he is soo annoying and obnoxious. HOwever, I found many moments where we cant help but see the soft side of Michael. I think it would be interesting to discuss some of those moments.

For example, The halloween episode, when he gives the candy to the kids.

The booze cruise talk with Jim at the end

The end of The Basketball episode where he calls off the saturday schedule.

Great thread, sweepthelegs!
How about during "Valentine's Day" when he takes the fall for Jan and tells her boss that he made everything up?

After the whole urine swap thing with Dwight, when Michael pulls some strings and makes Dwight security liason for the office, although he doesn't get to have a gun ( or a bowstaff)

Don't forget his thank you moment at the end of Office Olympics. The second sweetest tear-in-the-eye of the whole series.

When he goes with Dwight to the MRI so Dwight wouldn't be alone. When he rearranges his hair to match Jims. When he sang the "baby back ribs" song at Chilis. I agree also with the ending of Office Olympics when his "heart was full" and the end of the Booze Cruise scene when he was giving Jim a pep talk. And the fact that he wrote a screenplay with graphics is so adorable. :-)

Another good one was after Hot Girl, he talks about the one night stand and how he would choose his office workers over any one night stand.

I think that the premise behind Conflict Resolution is a great moment for Michael. Granted he goes about it in a terrible, horrible, no good, very bad way, but he has the best intentions. And no, it's not only to one-up Toby, but I think he sincerely wants to help his employees resolve their issues. I mean, he had the conflict book out and everything. He was dedicated to finding everyone a Win-Win(Pam: win) situation.

When he gives away Jim's big secret and then is really upset because he thinks Jim won't be his friend anymore. That was so pitiful.

I thought he was genuinely sweet when he was pulling Carole's kids around the rink with his hockey stick.

When he orders pizza for the guys in the warehouse and is glad to see that black people do, in fact, like it too.

It wasn't really a 'soft' side of Michael but I loved the look on her face when Jan realizes that Michael is going to get the sale in The Client - she is convinced that he is a total muck-up and then she sees that he is going to pull off the coup of the year for DM - Scranton! Go Michael!

The client, to Jan:
"well if it was a mistake, it was a wonderful mistake."

(not sure if thats verbatim, but loved the look on his face)

Lets not forget Michael's generous donation to Oscar's nephew's charity (the alliance). His face expression is priceless when he found out that it was 25 per mile.

when he took the time to look up skin cancer statistics to try and comfort kevin.