So I discovered a website called that awkward moment . net and I decided to reenact a bunch of awkward moments with the Supernatural characters. Aren't they just so fun to play with? They're like little voodoo dolls that you can poke and prod, and, in this case, put them in awkward/fail situations! Enjoy! ;)

Also, I'm debating whether or not I want to make more of these. What do you think?

Disclaimer: I don't own!

That Awkward Moment

That awkward moment when you're singing MC Hammer's 'Can't Touch This' and someone touches you.

Gabriel was sitting in his office in TV Land's show Dr. Sexy, M.D. singing along to the radio which was currently playing 'Can't Touch This' by MC Hammer. While he was distracted, a nurse approached him tentatively. When saying, "Excuse me, Sir?" didn't work, the nurse touched Gabriel's shoulder to get his attention. Gabriel, stopping in the middle of singing the chorus, stared at her scandalized. 'Can't touch this' indeed.

That awkward moment when the 9 year old you adopted from a questionable orphanage turned out to be the spawn of satan.

John and Sarah Smith walked out with their newly adopted little girl. He and his wife had spent a long time filling out paperwork. As they walked out, the orphanage owner's eyes flashed black. When they got home, the little girl turned around and started ordering them to do different tasks for her. "Darling, I don't think you have the authority to boss me around." John told his little girl. "Oh, but I think I do." The little girl said as her eyes went all white.

That awkward moment when your doctor asks if you're sexually active in front of your mom.

Ellen and Jo were at the doctor's because Jo had been feeling weird pains in her stomach, and they were sure it wasn't menstrual because that normally came later in the month. They came in, sat down, and told the doctor what was happening. The doctor asked a few questions, and Jo was fine with answering them until they came to one question; "Have you been sexually active anytime in the past few months?" There was an awkward pause. Jo hadn't, in fact, been sexually active, ever, but it was the principle of things. During that pause, Ellen stared at Jo, her stare getting harder with every second that passed. The doctor just stood there, feeling out of place in the stare down going on in front of her. Finally, when Jo couldn't take it anymore, she turned to the doctor and answered no. Ellen let out a sigh of relief; she wasn't going to have to murder someone.

That fail moment when someone say "Happy Birthday!" and you respond "Thanks, you too!"

It was Dean's birthday. He and Sam were celebrating it at Bobby's with Ellen, Jo, Bobby, Castiel, and Gabriel. Well, Gabriel was only there because it was a party. Dean didn't get many presents, but it was a lot more than what he normally got. Currently, he was standing by the table with a beer in hand, and staring at the presents, trying to guess what they were, based on their shapes. Jo grabbed her own drink and walked up to him. "Happy birthday Dean!" she said. Dean replied, "Thanks, you too! Er… wait…" Dean looked kind of confused and embarrassed at what he said, like he couldn't believe it came out of his mouth. Gabriel snorted from his place in the corner where he had conjured up the newest game console and was furiously racing Sam in Mario Cart.

That fail moment when you fall up the stairs.

Uriel was strutting past all of the mud-monkeys who thought that their jobs and lives meant something, going towards the stairs. There was no way that he was going to trust those things mud-monkeys call "elevators." As Uriel was walking up the stairs, his foot caught on the next step, and he went down like a ton of cupids. Uriel quickly got up and tried to brush off his suit like nothing happened. Next time, he was taking the elevator, mud-monkey contraption be damned.

That fail moment when you fall down a staircase with only two stairs.

Dean had just gotten into another argument with Sam, and ended up storming out of the diner. Dean was debating whether to or not to leave Sam at the diner when he saw Castiel standing by the Impala. Dean stalked towards Castiel worriedly, but he didn't quite make it. Dean had forgotten that the diner was higher off of the ground, and therefore had a couple of stairs leading up to it, and Dean fell faster than angels could fly. While Dean was groaning on the ground, Castiel was staring at him confused, and Sam was laughing at him from inside the diner.

That fail moment when you trip on the battery cord and do this weird hop to save your laptop from eternal destruction.

Sam was pouting. He had forgotten to charge his laptop earlier when he wasn't using it, and now when he did need it, it needed to charge. The wall plug was over by the bathroom door, and the table was on the other side. Dean had just gotten out of the shower and was walking over to where his bag was to get some clothes. Well, he was trying to, at least. The cord for the laptop was caught on his foot, and he started hopping backwards to keep the laptop from falling. Sam gave him a glare that said 'If you ruin my laptop, I'm harming the Impala.' The cord untangled from his foot, the laptop was fine, but his towel had been lost in the struggle, and Dean hurried over to his bag to finally get some clothes on. He liked being naked, but not in front of his brother.

That awkward moment when you're sitting in the theatre about to watch a movie and BAM, human giraffe sits in front of you.

Gabriel was sitting in the theater, watching the trailers while waiting for the movie to start. He was just starting to get interested in one of them when this super tall guy sat down in front of him. Gabriel scowled, and was about to start yelling at the guy for being so damn tall when he recognized the dude. Gabriel hopped into the seat next to the guy and said, "Hey there, Luci! How've you been lately?" Lucifer looked over at him and groaned. Gabriel was not someone you wanted with you when watching something; he talked too much. Lucifer decided that ignoring Gabriel was the best way to go, and just turned towards the screen. There was one thing wrong with that; some gigantic person had just sat down in front of them, and there was someone with him who was only slightly less taller than the other one. Both Lucifer and Gabriel were going to start complaining, until they caught a glimpse of who the people were. Lucifer leaned over to speak in the taller one's ear. "Hi there Sammy! I'm surprised to see you here." Sam paled.

That awkward moment when you tense your muscles and your shirt rips.

The laundry needed to be done again. Both Dean and Sam had been putting it off for a while now, and both of the brothers were left with only one clean shirt left. The problem was, these shirts no longer fit. Somehow, though, they managed to fit the shirts onto their bodies. Dean and Sam loaded their clothes into the Impala, and drove off to the nearest laundry mat. As Sam was putting clothes into the washing machine, they heard a loud tearing sound. Sam froze; his shirt had just ripped straight up one side. Dean looked up to see what happened and started laughing hysterically. Dean's shirt didn't agree with the movements made while laughing, and also ripped. Sam joined Dean's laughter, and the rest of the people in the laundry mat just did their best to ignore them.

The awkward moment when you go to grab somebody sexy and tell them 'hey', but your hand hits the mirror.

Dean stumbled into the motel room, shit-faced drunk. Sam was off at the library being a prude so Dean had the motel room all to himself. He had planned on picking up a girl, but then he got too drunk to remember to. He stumbled along the wall until he reached something. Dean looked over to see what it was. Oh, why hello there! He saw a very attractive man standing there looking at him. Normally Dean didn't go for men, but he could make an exception for this one. Dean went to go pull the man closer, and the man reached out for him as well, but there was some weird glass thing standing in the way. Dean got angry at the glass and smashed it, but as soon as he did, the other man went away.