A/N - Not only am I a huge Will & Grace fan, I'm also an avid lover of history so I thought I'd combine the two and explore the question of What if Will & Grace were set a century earlier? It's not supposed to be a hundred percent free of anachronisms - I threw in a few to maintain the feel of the characters - but other than that, it's pretty rooted in the nineteenth century (which is one of my favorite historical eras) I hope you enjoy!

1898

William Truman, a refined gentleman and esteemed lawyer, had had a busy morning writing up invoices on his new typewriter, and was taking a well-earned break admiring his freshly-groomed mustache in his hand mirror.

Lost in a reverie of his own handsomeness, he's startled when the door to his office bursts open. Standing there is of his biggest clients, Karen Walker, dressed to the nines in an extravagant feather hat and a flowing, yet well-tailored pinstriped dress.

William would be ashamed to admit, despite his misgivings about the socialite, that her dress alone was enough to take his breath away - albeit not quite in the way that one would expect from a thirty-two year old red-blooded male.

"Mrs Walker," he smiles, standing up and automatically reaching to adjust his tie. "You are, as always, a vision."

"And you look like hell. I thought I told you to do away with the mustache," Karen retorts.

William frowns, then hastily changes the subject.

"It appears you're actually early, for once," he says, pulling his out his pocket watch. "I wasn't expecting you until noon."

"Actually, I'm here about an entirely different matter," the woman says harshly, before stepping into the room, to reveal that she's tugging a struggling young man by the ear.

William furrows his brow.

"Let me take a guess - you discovered another peeping tom outside your chambers?"

Karen lets out a burst of sardonic laughter.

"You're slaying me! This nancy-boy here," she yanks his ear for emphasis, eliciting a pained squeal from the young man, "has been keeping me up day and night with that deranged tone-deaf bird of his, squawking at stupid o'clock in the morning. I can barely hear myself drink!"

"You mean think?" Will corrects.

"...Why would I do a thing like that?" Karen says, sounding offended.

"...Never mind."

"If you must know," the man finally speaks, tearing himself free from Karen's grasp, "the bird is called Guapo, and I'm teaching him to sing the National Anthem. We're a double act." He takes a moment to straighten out his suit. "We're going to be performing a duet at Carnegie Hall. We're going to make millions. Millions, I tell you!"

"...Jack McFarland, is that you?" Will says, instantly recognizing his old friend. "You're looking well."

"William Truman," Jack says curtly, his icy demeanor concealing his relief at encountering a friendly face. "You've...gained weight."

"It's good to see you too," Will smiles, accustomed to his friend's blunt asides.

Karen watches the exchange, and scoffs.

"Of course, the two nancy-boys know each other. I should have known."

Will stares at them both, and hits an open palm against his head.

"I'm sorry, I forgot to introduce you. Jack, this is Karen Walker, one of my most prized clients. And Karen, this is Jack McFarland, one of my…" he smiles sweetly. "...Dearest friends." He cocks his head. "Albeit one who hasn't contacted me in a long time."

"My deepest apologies," Jack says, "but I've been busy writing my one-man autobiographical play. It's called…" he braced himself. "...Jack with a J!"

"...Of course it's with a 'J'" Will replies. "What else could it possibly-"

"It's a working title," Jack snaps.

Karen is eyeing up Jack with renewed interest.

"You're an actor, you say?" she asks, her voice dropping to a drawl.

Jack tilts his head in consideration. "I suppose you could call me a thespian, though I've also dabbled in singing, dancing, composing…"

"...Shoe shining, chimney sweeping, bathhouse entertaining," Will finishes wryly.

Jack narrows his eyes.

"Well. I gave up on chimney sweeping. It was doing disastrous damage to my hair."

Karen smiles up at the young man.

"So you could say that you're a… jack of all trades?" she says.

"Yes, you could say tha-" Jack's eyed widen, stopping in his tracks. "Ooh, that's what I should call my show. Jack of All Trades!" He jumps up and down excitedly like a young boy.

Will shakes his head, smiling.

"Bully to you, Jack," he congratulates.

Karen trails her eyes down Jack's physique, and strokes her heavily powdered chin.

"Not very lucrative, though, is it?" she comments. "Say, why don't we strike a deal? You get that ghastly bird to shut up, and I will take you on a little excursion to a little place called Saks Fifth Avenue?"

"Oh, I've always wanted to go there!" Jack squeals, clapping his hands.

"It literally opened last week." Will says.

"I've always wanted to go there since last week!" Jack corrects, smiling down at Karen. Will rolls his eyes, but smiles at the unlikely friendship unfolding before him.

"You know, I'd also like a trip to the Midtown," he says idly. "I'd love to purchase the new Oscar Wilde book that-"

"You're not invited," Karen cuts in, smiling sweetly.

"Oh."

"Well," she continues, "I'll see you on Friday. For now, I have to get to my new job."

"You, a job?" Will says, surprised.

"Indeed, a job," Karen spits back. "A girl can't simply spend all day frequenting opium dens and tending to their husband's gout, you know."

"What job, if you don't mind my asking?" Will inquires, taking an idle sip of his coffee.

"If you must know, I'm posing for a new, up-and-coming artist," she says, her eyes flashing. "Nude."

Will lurches forward, nearly spitting out his coffee.

Jack gasps. "Posing nude? Why haven't I thought of that?"

"Which artist?" Will says, after composing himself.

"Grace Adler," Karen smiles.

Will's eyes widen in shock.

"...Grace Adler? As in...my Grace Adler?"

"That rather depends, is your Grace Adler a Bohemian, bony, red-headed, butch little Gibson Girl Jew?"

"...Yes."

"Huh! Small world, eh boys?" she cackles. "Anyway, I thought it best to immortalize myself in art while I'm still young."

Will bites his lip, resisting the urge to comment.

"Bye, boys," she says, throwing a wink at Jack before disappearing out the door.

Jack stares after her in awe.

"My word, I love her! Say, why haven't you introduced us before?"

"For whatever reason, I didn't predict the sheer chemistry," Will shrugs. He sighs, straightening his suit. "Well, I'm off, too, Jack. I have an important business meeting with a potential client."

"Oh?" Jack says, tilting his head suggestively. "Well, isn't that just a coincidence? I also have a business meeting with a potential client later this evening." He grins impishly. "His name is Javier. He works in construction."

Will fixes him with an incredulous look.

"No, I mean an actual, literal, business deal with an actual potential client!" he says, adjusting his necktie.

"Uh-huh," Jack says, staring at his nails and already losing interest. "Well, you are at least attending my show, correct?"

"...When - or rather, if you get a show," Will chides, glancing over his shoulder. "I will, of course, be in the front row seat."

"Throwing roses at my feet?" Jack says hopefully.

"Perhaps not quite," Will says.

"Oh, trust me, William. When you hear my modern rendition of Funiculi Funicula, you shall be. It may just be the next Lisztomania."

Will shakes his head, but laughs encouragingly and takes another sip of his coffee. "Rather."

"And also, it almost slipped my mind to tell you," Jack says. "I saw Michael yesterday in Coney Island."

Will freezes up, suspending his coffee cup halfway to his mouth.

"He was with a younger fellow," Jack continues airily. "They went on the ferris wheel together."

"The one at Steeplechase?" Will says shakily, and slightly higher pitched. He coughs in attempt to sound unabashed.

"That's the one. He didn't see me, though. I was hiding behind a lady's matinee hat." He laughs. "She accused me of attempting to steal the darn thing. I had to bite my lip to stop myself from telling her, nobody would want to steal it, matinee hats are quite out of fashion."

Will nods, not really listening.

"I have to go," he mumbles, grabbing his overcoat. "As previously stated, I have a … meeting."

He dashes out of the office without another word.

A/N Hope you like it so far! I had to make a few adjustments, i.e Grace's occupation - apparently interior designing didn't exist in the nineteenth century. I'm excited to introduce Grace (among many other characters who will gradually make an appearance. I'll try to include as many characters as possible) Let me know if you want to see a second chapter and I'll work on it right away!