Title: Matchmaker, Matchmaker, Make Me a Match

Wordcount: 579

Rating: PG

Characters: Azazel, Sam, Dean, Jess, mentions of Sam/Jess, Dean/various

Summary: Azazel is trying to find his boys "proper" companions- proper in this case being evil- but Sam and Dean just won't cooperate. Sam seems to be falling for this lovely, but unfortunately good, young woman named Jess and Dean isn't interested in settling down at all

Spoilers/Warning: You need to know who Azazel is. Otherwise, you're good to go.

AN: This… this story sprung pretty much fully formed out of my head during a IM conversation with pathsforme, who also provided a second look at the story. Anyway… it's crack, with added evil Sam and Dean.


Where had he gone wrong? Azazel frowned as he watched his boys laugh and joke. Oh, he wasn't upset that they were happy, what father would be?

But Sam and Dean Winchester, the humans he'd raised after possessing John Winchester twenty-two years ago, did not take any care in choosing companionship, and didn't like Azazel's choices.

Dean, it seemed, didn't want to settle down. He flirted and slept with any woman who caught his fancy, but those relationships never lasted more than a week.

Not that Azazel minded fornication, not at all. He just wished Dean would have just one relationship that lasted more than a month.

And Sam- Azazel sighed. Sam was always polite to the women Azazel set him up with, but he didn't really like any of them. Not the witches, not the demons, not even the completely human but completely evil ones interested him.

No, Sam's choices were almost always completely normal. This last one, however… Azazel groaned. Jessica Moore was completely human. She'd be perfect for Sam, except for the fact that she was good. Jess was pure, dedicated to helping others, and her soul was uncommonly bright. She just wasn't the proper sort of consort for the Antichrist.

Both neither of his boys seemed to care. Sam adored her, which was another thing that set Azazel's teeth on edge, and Dean seemed to already think of her as a sister.

Azazel really didn't need this. He watched the boys, Jess, and Dean's date of the week head out of the bar, and presumably back to the apartment Sam shared with Jess.

Azazel knew he couldn't just deal with Jess like he normally would a problem. Sam would never forgive him if Azazel killed her. He might even turn away from his destiny if he did that. So that was out. And he couldn't order one of his demons to possess her. Sam would see right through that. And Jess had already believed Sam when she caught another woman- just a student at Stanford- trying to kiss him. It probably helped that Sam had been trying to push the woman away without hurting her when Jess had found them.

There had to be some way to drive Jess away.


Dean escorted his date- a co-ed named Melissa- to her car and then returned to the Impala, where Sam and Jess were waiting.

"So, how long are we going to keep this up?" Dean asked as he slid in.

Jess grinned at him and pulled off the medallion she was wearing. The aura of brightness around her seemed to vanish, replaced by feel of a witch's soul. Dean started up the Impala and pulled away.

"How long do you think we need to?" Jess asked.

Sam smirked. "Well, it is nice to get a bit of payback for the last few times he's tried to set me up on dates," he said. "But if we let him think that you're a saint for too much longer, he might do something drastic."

"I give it another week," Dean said.

"At the most," Sam agreed.

Jess nodded and put the medallion back on. All three of them shuddered at the feel of goodness that invaded the car as she did so. "I will be glad when I can destroy this," Jess said.

"Me too," Sam said.

Dean smiled and turned up the music. Led Zeppelin sang on as they headed through the streets of Palo Alto.


I do hope you enjoyed this little bit of insanity.