Notes:

This story was written as a gift for aworldinside for the Yuletide Fic Exchange on Archive of Our Own. Now that the authors have been revealed, I can post it here for your enjoyment also I can properly thank my betas on this. Thank you to erinwert, rumpelsnorcack, and Claudia for helping me to refine this and fix up my silly typos. You all made this better.

The Worst Wingman Ever

The first time Fitz met Darcy, he was completely perplexed by him.

As a child, Fitz had never had much difficulty making friends. He was naturally outgoing and funny, and other children responded well to him.

William Darcy was a quiet kid who often stared into space with his brow furrowed and his lips set in a serious line. Despite Fitz's usually sunny disposition and winning personality, William Darcy did not seem impressed. The other children were, however, and every day at recess, Fitz had an endless supply of kids to play with.

Then, Fitz started to notice something about William Darcy that bothered him more than the fact that he didn't seem to be impressed by him; William Darcy was always alone. In the classroom, when all the other kids pushed their desks together to sit with their friends, William would push his off to the side. At recess, while everyone else was running around playing tag or soccer or swinging from the monkey bars, William would be sitting under a tree or up against a wall. Sometimes he had a book with him, but other times he'd just sit there, staring into space, looking contemplative.

It was on one of those days when William was staring into the distance that Fitz's curiosity finally got the better of him. He wanted to know why William never seemed to talk to anyone else, why he was always off by himself instead of playing like everyone else.

"Yo!" he said lightly, sitting down next to William. "I'm Fitz. Fitz Williams actually. We kinda share a name." Fitz laughed, but William didn't join in. Instead he just looked at Fitz, his eyes wide.

"You're talking to me?" he whispered after a moment, a hint of awe in his voice. "No one ever talks to me."

"Because you never talk to them."

William wrinkled his brow. "I do not know what to say."

A lightbulb went off in Fitz's head as he realised that William wasn't unfriendly, or snobbish, he was just shy and awkward. Not all kids were blessed the the kind of charisma Fitz had. Good thing, too, he thought, it made him more unique.

"Well, Darcy - Can I call you Darcy? That whole William Williams thing is confusing."

The other boy shrugged. "I guess."

"Great! Okay, so, Darcy, you could always start with something easy like, 'Hi'?"

"And then what? I am not interested in soccer or tag or other such trivial notions that everyone else is so enthusiastic about."

"You're always reading a book or thinking. What do you think about?"

"Everything."

"Everything? Dude, that's not possible."

"It's slightly hyperbolic but—"

"Hold up, hyperbolic? Man, you realise we're only in fifth grade right?"

Darcy shrugged. "I read a lot. My mother says I have an extensive vocabulary. I pride myself on that."

Fitz considered this. "Okay, then."

"Physics."

"What?" Fitz eyed the other boy in confusion. He wasn't at all what Fitz had expected.

"You asked me what I think about. Today I was thinking about physics and how the velocity of the cars going through that intersection changes based on the color of the traffic light."

"Green go, yellow slow, red stop. Everyone knows that, dude."

"It's more complex than that —" The bell interrupted his explanation and Fitz offered a hand to help him up. Darcy looked surprised by the gesture but, after a beat, he accepted and let Fitz pull him to his feet.

From that day on, Fitz would often join Darcy under the tree. Some days, Darcy would share his thoughts with him like he had on that first day. Other days, Fitz would talk and Darcy would listen raptly, hanging on to his every word. Sometimes Fitz even managed to convince Darcy to leave the comfort of the tree and talk to some of the other kids. The more they did that, the more Darcy seemed to be comfortable and have a better idea of what to say. He'd often look to Fitz for help if he was uncertain and Fitz was always happy to jump in and take over or get the conversation moving until Darcy felt more at ease.

The first time Fitz met Gigi, he was immediately enchanted. They were in middle school and Darcy had invited Fitz over to work on their science project. Gigi had pranced around the room as they tried to work, singing songs for Fitz and bringing him what must have been every toy in the house.

"I'm sorry, "Darcy said through gritted teeth. "Little sisters can be SO annoying."

Fitz laughed. "It's cool, dude. I think it's hilarious."

"You think everything is hilarious."

"Ouch. That really hurts, bro."

"You'll get over it." Darcy tossed him a marker. "Come on, we have a science project to finish."

Fitz sighed and got to work.

The first time Fitz saw Darcy cry was on the day of his parents' funeral.

Darcy stood by his parents' grave, Gigi clinging to his hand, as silent tears streaked both of their faces. Not wanting to intrude on the moment, Fitz observed from a distance at first, then slowly came to join them. He hugged Gigi first, then clapped a hand on Darcy's shoulder.

His friend met his gaze and Fitz was struck by how old Darcy's eyes suddenly looked. It was as though he had aged from sixteen to thirty in less than a day.

After that, things changed. Darcy was even quieter than usual, he was more contemplative, and his main concern became Gigi. The two had moved in with Darcy's aunt and Fitz rarely saw Darcy outside of school anymore.

The first time Darcy had a crush on a girl, Fitz knew he was in trouble. They were taking a college science class together (science had weirdly become their thing) and anytime a particular girl at the table next to theirs spoke, or laughed, or came near, Darcy would freeze up and either drop whatever he was holding or trail off from whatever it was he was trying to say.

After over a week of near disastrous mishaps (including one memorable moment when Darcy nearly spilled a caustic chemical on Fitz's foot), Fitz decided to take matters into his own hands. He coached his friend, giving him advice and even suggesting things to say, but even so, every time Darcy opened his mouth to speak, it would either come out rude, or not at all. It wasn't until the final day of the class that Darcy finally managed to get out a coherent, non-offensive sentence, but by that point, it was too late and the girl simply rolled her eyes and left the room.

The first time Fitz met Lizzie, he had not expected to like her. Darcy had always spoken of her with such a mixture of distaste and admiration that Fitz hadn't quite known what she would actually be like. To his surprise, she laughed at his terrible jokes, humored his silly whims, was incredibly interesting to talk to and Fitz took a liking to her right away.

The only problem was she seemed to have an incredibly negative view of Darcy, and if Fitz's suspicions were accurate (and let's face it, they usually were), his friend was actually quite besotted with her. So Fitz did his best to talk his friend up, to help Lizzie understand that Darcy wasn't being intentionally rude, that he was just awkward and reserved. He told her what a great friend Darcy was, how he had even prevented Bing from making a horrible mistake.

If only he had known that the girl Darcy had stopped Bing from dating had been Lizzie's sister, Jane, perhaps he wouldn't have nearly ruined everything.

The first time Fitz heard about Darcy's attempt at confessing his feelings to Lizzie, he cringed. When he saw the video later, it was like watching a train wreck happen in slow motion and he genuinely wished there was a way he could prevent the inevitable explosion. Unfortunately, it came anyway in the form of a massive bombshell and Darcy's broken heart.

"I'm so sorry, man," Fitz told Darcy after Darcy gave him a full account of his confrontation with Lizzie that afternoon. "I think I made things worse when I told her about Jane."

"It is not your fault, Fitz, it is mine. I should never have let my feelings overcome my better judgement." Darcy sighed. "So these videos, you've seen them?"

Fitz shrugged. "A few. Lizzie's pretty funny in them."

Darcy nodded and pulled out his laptop. "I guess I have some catching up to do then."

The first time Gigi watched Lizzie's videos, Fitz followed her tweets about them with great interest. As soon as she was fully caught up, she called him.

"So, obviously we know my brother likes her," she began without preamble. "Well, loves her actually."

"Yep. His feelings are genuine, although I think we can agree he didn't go about telling her in a way that was conducive to any form of reciprocation."

Gigi laughed. "Isn't that the truth." She paused. "Regardless, I think that perhaps there's still a chance."

"As do I," Fitz agreed. "Lizzie seems to be reevaluating everything since he gave her that letter."

"I agree, but I also don't trust my brother to do this on his own. We both know how hopeless he is in these kinds of situations."

Despite the fact that Gigi couldn't see him, Fitz nodded. "Boy do I ever."

"So should we do something about it?"

Fitz grinned. "I'm already on it."

The first time Fitz really started to believe that their plan was working was the day Gigi and Darcy took Lizzie sightseeing in San Francisco.

Fitz watched with rapt interest, feeling a certain measure of success as pictures rolled in on twitter (along with a few covert shots that Gigi had texted him privately)

Then he checked twitter and saw this exchange:

Lizzie Bennet: wmdarcy Thank you and Gigi for an awesome day.

William Darcy: TheLizzieBennet Our pleasure.

He grinned and immediately called Gigi. It was time to celebrate a job well done.

The first time Fitz watched Lizzie's 98th video, he was without words. All he could manage was to bounce and flail his arms as he made a sort of squeaking sound and beamed like a loon while he observed his friend finally finding happiness.

As soon as the video ended, he hit play again, feeling an absurd need to confirm that he hadn't imagined the whole thing. The second time around, his reaction was just as incoherent as the first and by the fifth, he was practically bubbling with joy. Darcy, the shy little boy who didn't know how to talk to other kids at school, and who had a talent for making an absolute fool of himself around girls he liked, had finally managed to communicate effectively enough to land the girl of his dreams.

Fitz beamed with pride as he tweeted back and forth with Gigi about the video.

He may be the worst wingman ever, but no one could deny that he was the best covert matchmaker ever. Well, one of them.

Fin