Disclaimer: I don't own any of this. But if they're interested in selling Will and/or Jack, someone let me know, okay?

Summary: Fans of Friends might recognise the basic idea for this story. What might have happened if things had gone differently in the flashbacks in 'Lows in the Mid '80s'? What if Will and Jack had gotten together when they were teenagers? What if Will and Grace never reconciled after their breakup? What if Karen never married Stan, but still had Rosario come to work for her?

Chapter One

The jewellery department was almost empty. Outside the cold late-autumn winds were raining red and yellow leaves against the big display windows in irregular bouts. The lone salesgirl smiled disinterestedly at Will before returning to her magazine.

Will perused the glass cases, feeling nervous and a little out-of-place. Having never been called upon to buy this kind of gift before, he was totally out of his depth.

"Excuse me?" he called to the salesgirl. She put down her magazine – managing not to look too put out – and walked around the counter over to where he was standing.

"Sir?" she asked politely. Her nametag read SALLY.

"I'm… um… looking for an engagement ring," Will said, sounding as awkward as a newly-of-age kid buying his first pack of condoms. Come on man, you're thirty-seven, he scolded himself.

The girl gave him a puzzled look and started her spiel. About three-quarters of the way through the elevator doors opened and deposited a flustered-looking redhead woman in a long coat and a zig-zag-patterned dress which was almost certainly a mistake. She went over to the sales counter and re-arranged her windswept hair while she waited for the girl to finish.

Eventually, when Sally had left Will equally as undecided as he had been beforehand, the woman started to speak.

"Hi, I've got a couple of things I'd like to return," she said, rummaging through her spacious handbag and depositing a couple of small display boxes on the top of the desk.

"Okay, do you have the receipts?" Sally asked, smiling that flawless, genuine smile that only very new salespeople can manage.

"Here's the thing," said the woman, and Will looked up, suddenly certain he knew her from somewhere. "They're my wedding and engagement rings from my adulterous soon-to-be-ex-husband, and if there is any way I could return them without the receipts then I'd really like to know about it, please."

Sally's brow furrowed. "I'm in a little over my head here," she said after a moment. "I'm just gonna go get my supervisor."

She swept over to the EMPLOYEES ONLY door at the back of the room and was gone.

The woman turned around and her eyes locked on Will's. "Oh, my God," she said, almost instantly, "Will Truman? Is that you?"

Will thought back desperately, searching for a name. One made itself known very quickly. "Grace?" he exclaimed.

Her face lit up in the familiar smile. "Yeah!" she squeaked, going over to him and giving him a brief hug. "Wow! Fancy meeting you here!"

Will nodded. "How long has it been?"

She thought for a moment. "Must be something like… eighteen years. Woah."

"That long?" he asked. "I thought it had only been about five or six. Are you sure?"

"Yup," she replied. "Definitely. We were nineteen the last time we spoke, remember?

"So what brings you to the Tiffany's jewellery department?"

"Well," he said, "Hopefully I'm about to get engaged. I've already heard what brought you here," he added, smiling slightly.

"Oh," she said, blushing, "You heard that, then?"

"Grace, the entire block heard it," he grinned, teasing her as if they'd been apart for mere days instead of nearly two decades, and as if their last meeting had ended on friendly terms.

"Okay, so my problems have been broadcast to a not inconsiderable part of Manhattan's population," she said, "But tell me all about the lucky guy."

Will reddened slightly, remembering their break-up. "Didn't forget that, then?" he asked.

"How the hell could I?" she inquired. "I was down about it for almost three years. But I'm not still mad at you, if that's what you mean. Eighteen years forgives a lot. Plus I've got a new vent for my anger towards exes – Dr. Marvin Leo I-Can-Save-The-Third-World-But-Not-My-Own-Marriage Adultery-Committing Marcus, the lying-cheating bas – so tell me all about your husband-to-be."

The abrupt change in conversation threw Will off for a moment. "Oh," he said, once what she had asked had registered. "Um… It's our seventeenth anniversary in two weeks' time and – "

"Seventeen years?" she asked. "So you've been together since you were like, twenty?"

Will nodded. "He was nearly nineteen, I was just turned twenty."

"Wow," she said, "I wish I could find that level of commitment. Although obviously it was too much to ask of a certain two-timing Red Cross Aid Worker-seducing – quit holding out on me, what's his name?"

Once again, Will took a moment to figure out what she was saying. "His name is Jack McFarland," he said. "I think you met him at a party once, when you and I were still, you know, together – but you probably won't remember him."

Grace pondered on this for a moment. "The high school kid with braces and blonde streaks in his hair?" she asked after a moment. "The one at Matt Stokes's who couldn't take his eyes off of you the whole night?"

Will nodded, unable to avoid grinning. "I guess, although I hadn't noticed the last one," he admitted. "But I would like to point out the braces and blonde streaks are a fond but fortunately distant memory."

"Well, I guess a lot of things seemed like a good idea back then," she agreed. "We were kids, it was the '80s, everyone had bad hair."

Sally burst back through the Employees Only door. "I'm sorry, my supervisor is unavailable right now," she said, "But she looked at the items in question and doesn't think they can be returned very easily, especially without the receipts."

Grace rolled her eyes in annoyance.

"Sir, do you need any more help?" Sally inquired politely of Will.

"No thanks," Will replied quickly, "I'm gonna think on it for a while and come back tomorrow, if that's okay."

"Alright, sir," Sally said, and smiled.

Will and Grace made their way towards the elevator. "Wanna get lunch or something?" Grace asked.

"Sure," he replied. "I know a good place."

"Great! They don't sell carrot cake, do they?"

"I don't think so," he replied.

"Oh, thank God!" she exclaimed. "No self-respecting cake should be caught fraternising with vegetables. I refuse outright to be in the same room as the traitor cake."

Will grinned. "It really is you."

TBC...