ETA: Thanks to SignedOG, who pointed out that there is no 4th Ave uptown. Although I'm not quite sure there'd be a "little coffee shop" on Madison Avenue, so sorry if I'm still screwing everything up.

AN: Holy crap I did a bunch of research on this. It's unfinished right now, but I'm hoping against hope that I'll finish it sometime in the next few days and then post it periodically. I'm really tired of having unfinished WIP's laying around.

Disclaimer: John Hughes owns this. Oh. And he owns everything you recognize as Breakfast Club.

Chapter One

Shermer, Illinois, 1984

Claire bit her lip, shuffling uncomfortably in her desk chair, eyes once again taking in the phone number written on the top sheet of her stationary, right on top of the letterhead. Seven digits that would change her life as she knew it.

Claire frowned at the numbers, wearing a hole in her lip even as she contemplated what she was planning to do. Last night at Stumpy's had been a disaster of epic proportions (or so she was told) – Andy had brought Allison. Andy had brought basketcase Allison to a party full of jocks and populars, and it had been a disaster. Half the girls at the Shermer were now refusing to even acknowledge Andy's existence (beyond the piles and piles of gossip being spread like wildfire) even though Friday afternoon had had most of them mooning over him.

And what Claire was planning to do would pretty much solidify the entirety of Saturday's delinquents as outcasts.

Claire felt a rush like she'd never felt before, and gritted her teeth for a moment before picking up the receiver and dialing out the number.

It rang three times before anyone answered, and then it was a young voice that answered. "'Lo?"

In the background, Claire heard a woman yelling "Henry, I told you not to answer the phone! Who is it?"

"Who is it?"

"I…it's Claire Standish."

"She says her name is Claire!"

The answer was garbled, but Claire caught "…she want?"

"What do you want?"

Claire dug her teeth into her bottom lip again. She could still back out. Still be Prom Queen, still go shopping next Friday with Annabelle and Rose.

"Hello?"

Maybe 'Henry' would get impatient and just hang up on her. But she'd be mortified if he mentioned that Claire had called. She was conceited, and she was a bitch, but she didn't want to be those things.

"Yes, can I speak to Allison?"

New York City, 1992

Claire tugged at the collar of her shirt, bemoaning summers in New York for perhaps the twentieth time that day as she made her way up 5th Avenue, dodging two disgruntled looking models stomping past in a flurry of cheap runway knockoffs that were the next issue of Vogue's fashion flubs. At least, if her article got to print, they would be.

She swung down the street at a dizzying pace, and made to turn onto East 44th. Only instead of finding an empty walkway she walked straight into someone turning onto 5th.

Papers and manila folders went flying everywhere, and as Claire stumbled backward, attempting to keep her footing on the Blahniks she was trying out in preparation for next months fall fashion issue, while the man she'd bumped into bent and began furiously reaching for the papers that, thankfully, had merely floated to the sidewalk.

"Oh, I'm so sorry!" she said, bending to help the man.

"No, no, it's okay, they're just really important financial figures for the upcoming quarter, really, it's no big deal."

Claire paused as the voice registered in her brain, and she glanced up at the man kneeling beside her. He had broad shoulders tapered to a narrow waist, and a shock of blonde hair slicked back in the style Claire had seen many a Wall Street employee wear. He glanced up at Claire after a moment too long of her studying him, and she smiled at the blue eyes locked onto her own.

"Claire Standish?"

Her smile widened. "Hey, Brian."

"Oh, man, you – you look great! I mean, of course you do, you've always looked great, but… Hey, how are you?"

"I'm pretty good. How are you? What are you doing here?"

"Yeah, I'm excellent. I'm here on business. Accounting stuff, financial…things. It's really boring."

"You're an accountant?"

"More of a business partner, really. I mean, it was a joint venture, and I guess John sort of owns a larger portion than I do, but we make the same amount of money, so…"

Her heart skipped a beat. It couldn't – "John?"

"Hmm? Oh – yeah, Bender. I mean, small world right? Who knew?"

Claire handed Brian back a final piece of paper, and they both stood. "John Bender? You…opened a company with John Bender?"

"Yeah, yeah, a few years back." He paused, and scratched the back of his head, and Claire saw again the sixteen-year-old who'd wanted to kill himself with a flare gun. His face had filled out, but he was still there in Brian's mannerisms and his speech. "We make lamps."

Claire tried not to smile too wide at that.

"Listen, do you want to go for coffee? I know this place just up the street…if you're not busy?"

Brian's eyes lit. "No, no, I'm not busy. Coffee – well, I don't actually drink coffee, because it does something funny to my system and I get a nervous tic, but – yeah, that sounds great. Talking. Not the nervous tic."

Claire grinned back at him, nodding her head in the direction of Madison Avenue.