A/N: I can't get Supernatural off the brain lately. So, I figured I'd better start writing so I can get at least some of it out of my system by November (so I can write an original story for NaNoWriMo, of course). I'm planning on having 101 chapters total (as referenced by the title) but I only have a quarter of the AUs decided on. Requests are welcome!

Chapter 1: A First Attempt

Gabriel mussed his hair. The lighting in the Men of Letters bunker's library was a little dim, and maybe could have been romantic if not for the miles and miles of books on how to kill supernatural creatures that lined the walls. Well, if you didn't know what they were about, maybe it could still be romantic. Sam liked books, right?

That wasn't the point though, and Gabriel knew he was stalling.

"So, look," the archangel propositioned shakily. "What I'm trying to say is I think we should go on a date. Get some coffee. See the Louvre. Snag some chocolate in Switzerland. You know. Start out casual."

Casual. That was funny, right? Casual. And maybe it was a bit of a security blanket to bring up his powers, like that showed what a catch he was, but why not? After all he would have no qualms about zipping Sam anywhere in the world, as long as they were together. There was a heavy silence. Gabriel laughed nervously just to break it, and Sam stared at him.

"A date?" the hunter asked, crossing his arms over his chest. "The Louvre?"

"Y-yeah, well, come on, gigantor!"

Sam massaged the bridge of his nose and sighed. Gabriel's heart sank.

"Gabriel, I… I don't even know where to start with this," Sam said. "First of all, do you honestly think I have enough down time to go skipping off to Europe with you? Some of us actually try to, you know, help people."

The archangel shrunk into himself a little, only daring to meet Sam's eyes in quick darting glances. What he saw there was not reassuring.

"W-well, but I-"

"Secondly, why would I even believe that this is an honest offer at all? When have you ever shown any kind of romantic interest in me?"

"There was the time I-"

"And another thing. Yes, you've helped Dean and me out a few times, but that's it. We were never friends, let alone the potential for something more. I don't know why you bothered saying all this in the first place, honestly."

Gabriel's jaw tensed, and he blinked hard a few times but not to fight back tears or anything because he was a Trickster and an archangel and he didn't give a shit what one little hunter thought of him. Only that was the whole problem; yes he did. Swallowing hard, Gabriel snapped his fingers before Sam could say anything more painful.

The scene around him, Sam included, dissolved.

"One more time," the archangel promised, trying to psyche himself up. "One more time, and I'll get it right."

Gabriel snapped again, and the act started over from the beginning.

"Gabriel?" Sam asked, furrowing his brows. "You're… You're dead."

The angel plastered on a smile and shrugged.

"Can't get rid of the Trickster so easily, Sammy!" he exclaimed. "Here. I'll prove it's me."

With a snap of his fingers, a platter of chocolate-covered strawberries appeared. Gabriel took one off the plate and popped it into his mouth before offering the tray to Sam. Frowning, the hunter waved him away. With a practiced sigh, one perfected by twenty previous attempts, Gabriel set the strawberries on a nearby table.

"Alright, you're you," Sam relented. "What do you want? You've been dead, or at least pretending to be, for like five years now."

"Just busy, archangel stuff. But that's not important. Thing is, I realized something and I…"

Gabriel struggled for a moment. His script had run out, and he needed to find something to replace the previous disastrously received dialogue with.

"You?" Sam prompted impatiently.

"I wanted to say I'm sorry," Gabriel said. "About… Well, lots of things. I'm sorry about Mystery Spot, even though it was hilarious-"

Sam's unimpressed look cut Gabriel off, and the archangel mussed his hair.

"Well, nevermind about Mystery Spot," Gabriel stammered. "I'm sorry I didn't help more, with you and your brother, the whole Apocalypse thing. I'm sorry I haven't come back to help you since then. I'm… Pretty useless, huh?"

"Basically," Sam replied.

Gabriel flinched and snapped his fingers to make Sam disappear.

"This is harder than I thought…" he muttered to himself, pressing the heel of his palm over his heart. "I can't take much more of this."

"Gabriel. What are you doing?"

The youngest archangel whirled around, putting on a shit-eating grin just for his eldest brother.

"Mikey! What are you doing here, bro?"

But Michael just looked at him steadily, and did not respond. Gabriel shifted from foot to foot. He glanced around a little, noticing with some mortification that though he had snapped away the illusionary Sam, they were still standing in the Winchesters' bunker. Gabriel chanced a look at Michael's eyes. They were steely and unwavering.

"Nothing important…" Gabriel said at last.

"You have been simulating conversations with Sam Winchester for the past hour. Why?" Michael demanded.

"You wouldn't get it," Gabriel huffed, petulance rearing to the forefront in an attempt to annoy his brother off the scene.

"You want to start a romantic relationship with him. What is there to not get, aside from why?"

The look on Michael's face was one of no little disdain. Gabriel's smile twitched and faded.

"What do you mean why?" he snapped. "Sam is- he's- he's pretty and smart, not to mention he completely pulled one over on you and Luci, by the way, and he gets this look in his eyes that's just- and the way he says "so get this" when he's found something for a case and-"

Gabriel trailed off when he realized he was rambling. Michael looked even more unimpressed, if that was even possible. Gabriel stuck out his tongue at his big brother.

"This is a waste of your time and energy, Gabriel," said Michael. "You should be helping to restructure Heaven."

"No!"

Even Gabriel was surprised by the sharpness in his tone. Michael took a step back. Squeezing his eyes closed, Gabriel took a shaky breath. He held up both hands, a gesture common between the brothers before their estrangement; Gabriel's signal for 'give me a moment'. With an uncomfortable frown on his face, Michael waited.

"No," Gabriel repeated. "Not until I get this right. I have to- I have to get this right. Please, Michael."

The look in his eyes was uncomplicated; simple, strong desire. For his own well-being, Michael realized, Gabriel had to finish this. Whatever this was, and no matter how frivolous it seemed to him.

"Alright. Fine," Michael relented.

He was gone with a soft fluttering sound, and Gabriel let out a long breath.

"Thanks bro. … Once more, with feeling. Come on Gabe."

With a click of his short fingers, the scene began again. The Men of Letters Bunker, take twenty-five. But he was so worked up he had forgotten how he was supposed to start.

"Look, Sam, I know I messed up-"

"Gabriel?! Dude, what the hell?" Sam demanded, practically falling out of his chair.

Gabriel flitted to his side, to make sure he was steadied, but Sam pulled away sharply.

"Sam, please."

"Please what?" the hunter asked. "You're dead, why are you here?"

"No, I'm not dead. I was hiding out in Heaven. Look, Sam, that isn't… It's not important, I'm here because-"

"Because what?" demanded Sam. "Whenever you show up, it always means trouble."

"What? Come on, kiddo, I'm not that bad, am I?" Gabriel asked with a weak smile.

Sam set his jaw harshly, and Gabriel snapped his fingers.

"Ok," he relented to empty air. "I am that bad. But I can do this. I know I can! I'm the Trickster! If I can get those two yahoos at each other's throats in a day, I can get one of them to fall for my charms!"

The archangel went to snap his fingers again, but after a moment's pause lowered his hand and frowned. Mulling over an idea, he shifted his weight from foot to foot. His golden eyes zipped back and forth as he debated, and then with a contemplative frown and a shrug, Gabriel snapped his fingers again.

The dim, silent Men of Letters bunker vanished. Instead, the white noise of a huge crowd buzzed in Gabriel's ears, and everything was bright and colorful. A perfect blue sky sailed overhead, and the smell of ice cream and turkey legs wafted through the air like a college boy's cologne.

"Maybe we just need a change of scene, huh Sammy?" Gabriel asked rhetorically, a grin on his face.

And what better place to start his journey to suave, Sam-seducing confidence than the Happiest Place on Earth?