When Jack overhears Will describe him to Grace as someone border-lining on pathetic, Jack decides to mess with Will.

Jack and Karen stumble into a life they never expected.

Inspired by the season 8 episode, "Forbidden Fruit". The first part of this story follows Karen as a new mother and the second part follows Karen's relationship with her daughter as she grows up and begins to discover herself and who she wants to be. In progress and still actively updating!

While walking in a bad neighborhood at night, Karen and Will get mugged by a violent, crazy man with a knife. Karen is scared to report their attacker to the police and Will feels responsible for the whole thing.

There was always one thing Grace could count on whenever she met Karen for a drink: there would always be someone who was confident he could worm his way into the socialite's heart. It used to bother her, thinking about what would happen if one of them actually succeeded...until she learned that she was the one who held Karen's heart so that none of them could.

Karen gets some new that will turn her whole world upside down, and she needs the help of her best friends to deal with what is going to happen. Note: this story takes place after season five, and Stan Walker is really dead.

When Will and Jack are away on their summer vacations, Grace and Karen fall into a brilliant three-week romance. But once the boys return, their brief relationship becomes a secret, never to be mentioned or acted on again. That is, unless Grace can muster up the courage to tell Will exactly what Karen means to her.

"Somewhere in heaven." Will said to the stranger next to him. "Somewhere in heaven there's a designer, a socialite and an actor reeking havoc on the afterlife."

For as long as they've known each other, Karen was the one Grace went to with her relationship troubles. When Leo Markus came along, Karen instantly hated him. But as time went on, and she helped Grace through all of the things Leo put her through, she started to realize her reasons for hating him went deeper than she thought. And she started to realize her own feelings for Grace.

It's Valentine's Day, and Karen wants to finally ask Grace out on a date.

Once upon a time, Grace and Karen accidentally created a holiday tradition in Grace's hour of need. Fourteen years later, after they let that tradition fall to the wayside, Grace decides to dust it off and give Karen a reason to smile.

Grace finally realizes why it feels so good to hear Karen call her "Honey."

For as long as she can remember, Karen has kept a diary dedicated to the ones she loved and lost, the ones who left, the ones who broke her heart. She could tell from the start that Grace wasn't like the others. But her history is daunting, and her walls are built high. And she knew that sooner or later, that diary would dictate their story.

This thing (whatever it is) between Will and Jack is so new that they're hiding it from Grace and Karen. Both men, however, are aware they need to discuss their future.

What happens when a mysterious man meets Karen at a bar? What hapens when they realize that man is also Jack's son?

Drabbles containing moments between Karen and her stepkids throughout the series (both old and new!). Chapters in no particular order. Prompts welcome!

Jack tries to help Karen deal with the loss of her husband.

Continuations and variations of the many Jack and Karen moments throughout the series. Rated T for now

Jack's incident with a stripper at a party leaves him lost and confused. Karen tries to help him out.

Part 2 of the Friend's Shouldn't Kiss Like We Do series. Karen is pregnant and Jack is the father. Rated T (for now)

Reality sets in as Karen has to deal with the fact her and Jack can never be together in the way she longs for.

It's Jack's turn to take care of Karen when she needs him most.

Karen witnesses the breakup between Grace and Nathan and does what she can to make Grace feel better. Just a little fluffy :)

ESCORT AU Grace has a wedding to attend and no one to go with, but Will is too busy to go with her. However, he has a friend who owes him a favour, an escort he knows as K. Grace is desperate, and accepts, but what will happen when she finds out K is not exactly what she imagined? Grace/Karen

Will and Grace unexpectedly switch lives in a Freaky Friday style body-swap. Because why not? [WIP]