Plot: Karen's younger brother comes to town with a few surprises for his sister.
Author's Note: Special thanks to Alice for helping me with the plot and title.
Disclaimer: I don't own "Will & Grace", Jack & Karen, or anything else in this story except for the character of Conner Delaney who is a creation of mine. Please don't sue me.

Guest-starring Brendan Fraser as Conner Delaney

It was 11:00 in the morning at Grace Adler's office and, big surprise, her assistant, Karen Walker, was nowhere to be found. But this didn't stop Grace from scheduling her clients and gathering materials together for a loft she would be designing the next day. It seemed like today would be just another ordinary day at Grace Adler Designs.

At least, that's what Grace thought. Just as she was getting ready to place a phone call, a nearby pile of carpet samples began to lean dangerously. As Grace rushed to catch them, a young man walked in. Grace had her back turned to him, struggling to get a hold of all the samples, but they quickly slipped out of her arms. She groaned, then stooped down to pick them up.

"Oh, let me help you," the man said, startling Grace. She whirled around and noticed for the first time the young twenty-something standing by Karen's desk. He walked over to the spilled samples and quickly helped gather them up. Grace smiled, partially in response to his help, and partially because this guy was really cute.

"Thanks," Grace said, putting the samples into smaller piles. She paused, then looked at the young man. "I'm sorry, but who are you?"

"I'm Conner," he said, holding out his hand. Grace shook it.

"Grace Adler, " she replied. "Not to sound rude, but is there something you want?"

"Actually..." he began, but stopped as Karen walked in, carrying an armload of shopping bags.

"Hi honey," she said absentmindedly to Grace, not bothering to look at her. Karen dumped the shopping bags by her desk, then picked up a nearby catalogue and began to flip through it.

"Uh, Karen, it's eleven...oh, never mind," Grace sighed. "Conner, this is my 'assistant'-"

"I know," Conner said, smiling. He walked over and leaned down until he was eye level with Karen's catalogue, then said, "Hey Kare".

Karen looked up, startled, then noticed the young man starring back at her. Her face broke into a smile.

"Conner, honey!" she exclaimed, standing up and embracing him. "What are you doing here?"

"Well, I told you I was coming to New York in my last letter," he explained. "I found out where you worked and I decided to surprise you."

"Oh, sweetie, it's great to see you!" Karen replied, hugging Conner again. Meanwhile, Grace watched the scene with a very confused look on her face.

"How do you two know each other?" she finally asked.

"What?" Karen said, still not paying much attention to Grace. Then she focussed in. "Oh, Grace, I'd like you to meet Conner Delaney, my little brother."

"What?" Grace said, surprised. "Since when do you have...blood relatives?"

"Honey, do I have to tell you every little detail of my life?" Karen asked. "Conner's been studying away in Egypt this past year, and in England for five years before that. My little scholar."

Conner smiled, then turned to Grace.

"Karen's told me so much about you," he said. "How's your husband, Will?" Grace glared at Karen.

"Honey, how about me and you go out for lunch, catch up things?" Karen asked, returning her attention to Conner.

"Great, when?" Conner asked.

"Now," Karen replied matter-of-factly.

Ten minutes later, Karen and Conner were sitting in one of New York's most elegant restaurants. After placing their orders, Karen turned to her brother and asked, "So what've you been up to, honey? Anything interesting happen in the last few months?"

"Uh, actually, yes," Conner replied. He looked nervous and started fiddling with his fork. Finally, he looked at Karen. "I have something I have to tell you. Now, I know you're probably going to be fine with this and I'm worrying about nothing, but...well, here goes."

Karen waited and Conner continued playing with his fork for a few minutes, then finally put in down and looked at his sister. "Karen, I'm...I'm gay."

Karen felt her eyes widened, but when she saw the nervous expression on Conner's face, she smiled. It was a bit of a surprise, but at least it wasn't a bad surprise. She reached out and took Conner's hand in hers.

"Sweetie, that's great," she said. "I'm so happy for you. When did you realize this?"

"Well, probably during my time in Egypt. There were some really cute guys in my tour group," he said, grinning. Karen grinned back.

"Do you have a boyfriend?" she asked.

"Uh, no," he said. "I mean, I've dated, but I haven't met anyone who I'd want to have a serious relationship with yet."

"Well, honey, you've come to the right place," Karen replied. "I'll do my best to help you find the perfect man. Or at least a man who will do for a few weeks."

"Thanks, Kare," Conner said.

At that point, their food arrived and conversation stopped for a few minutes. Then Conner brought up a new topic.

"Have you spoken to mom lately?" he asked.

Karen rolled her eyes and made a face.

"Kare, I know you two don't see eye-to-eye-"

"She's a bitch, Conner."

"-but it would really be great if we could all be in the same room together without you calling security and having her dragged out."

Karen sighed and put her fork down.

"Sweetie, it's not going to happen. Not unless the room we're all in together is the funeral parlour and she's the one in the box, and even then there might be exceptions," Karen said.

Conner sighed. He could tell this wasn't going to work.

"So how's Stan?" he asked, changing the subject before Karen could start her tirade about why she hated their mother.

"How should I know, honey?" Karen joked. "He's been out of the country for a week and the money keeps rolling in."

"When do I get to meet this Jack you're always writing about?" Conner asked. "He seems like a really interesting guy."

"Oh, honey, interesting doesn't begin to describe Jack," Karen laughed. "But I'll tell you what, he's meeting me at work in a little bit, why don't you hang around and I can introduce you?"

"Sure, sounds fun," Conner replied.

An hour later, Karen and Conner were back at Grace's office. Will was there as well, anxious to meet Karen's brother. While Karen went back to her catalogue, Will and Grace dragged Conner over to Grace's desk.

"So what was Karen like as a child?" Will asked, grinning gleefully.

"Well, guys, I'm not really sure," Conner replied. "Keep in mind, she was 14 when I was born. But she's the best sister I could ask for. One summer when I was 8 and I broke my leg, she drove down from college just to spend time with me to make sure I wasn't bored stiff."

"Oh," Will and Grace replied, disheartened that Conner didn't have any good details about Karen.

"I only wish she and mom got along, but I can't ask for everything," he continued, sighing.

"Did Karen really have your mom committed?" Grace asked.

"Yes, but after the doctor's found out she wasn't really crazy, they let her go. They haven't spoken since," Conner said sadly.

At that moment, Jack came in.

"Hey Kare," he said. "Ready to go?"

"Sure, honey, just a sec," Karen replied, standing up. "Conner, sweetie, come here."

Conner turned and joined his sister.

"Conner, this is Jack," Karen said. "And Jack, this is my baby brother, Conner."

"Your brother? Since when do you have a brother?" Jack asked.

"Honestly, do I have to tell everyone every little detail of my life?" Karen asked.

"If it's me, then yes!" Jack replied. He turned to Conner.

"How do you do?" Conner said, holding out his hand.

Jack took Conner's hand.

"Well, I see good looks run in this family," Jack said. Conner blushed and smiled.

"Jackie, be a dear and take Conner to the clubs with you tonight?" Karen said. "I promised him he wouldn't leave New York without a boyfriend in tow, or at least a couple of phone numbers."

Conner looked at his sister in surprise.

"Kare-," he began, but Karen silenced him by putting her fingers to his lips.

"Sweetie, it'll be fun," Karen replied. "Just go out there and have a good time. Now, where are you staying?"

"The Holiday Inn," Conner told her.

"Here, honey, take my keys," she said, handing him her keys. "No brother of mine is staying at a crummy hotel. You can sleep in Rosario's room. I'll just have her sleep under the pool table again."

"Thanks, Kare," Conner replied.

"So Conner, you read to go?" Jack replied. "I think we'll start at the Atom Barr and work our way up. C'mon!"

Conner planted a quick kiss on Karen's cheek, then he and Jack left.

"Wait a minute, Conner's gay? When did - oh, never mind," Grace said, seeing the look Karen was giving her.

That night, or rather, early the next morning, Conner arrived at Karen's penthouse. He wasn't surprised to see her waiting for him.

"Hey, honey, how were the clubs?" she asked.

Conner beamed.

"They were excellent, Kare," he said, embracing her quickly. He spun around a few minutes, humming.

"Well, you look like you had a good time," Karen commented.

"Oh, Kare, I think I'm in love!" Conner exclaimed.

"Well, honey, that's great! Who's the lucky guy?" she asked.

"Jack!" Conner exclaimed.

Karen stared at Conner, wondering if he was serious. When she saw that she was, she sat down on the nearby couch and repeated, "Jack?"

Conner nodded and joined Karen on the couch.

"Well, I mean, he doesn't know yet," Conner explained. "But, oh Kare, he's the best! He's gorgeous and funny and a great dancer and a great singer and he has the most wonderful personality. I just love him!"

Karen paused, still in shock.

"Well...are you actually going to do something about it?" she asked.

"Actually...I was going to ask him out tonight, but then I thought maybe I should get your approval first. I mean, he's your friend and if you don't think I should date him, I won't," Conner replied. Then he grinned. "But I hope you say I can!"

Karen thought for a minute, then sighed.

"Honey, I don't know...," she began. "I mean, Jack is a dear, but...well, he tends to, uh, go through men fairly quickly. Y'know, one in the morning, one in the afternoon, a few at night..."

"But I could make it work with him, I know I could!" Conner said desperately.

"Honey, you know how many men have probably said that?" Karen replied. She sighed. "Give me some time to think about it. I mean, even if it did work out, what if you two broke up? I mean, who would I comfort, you or Jack?"

"We wouldn't break up though!" Conner said. "Please, Kare, just let me have a try. I've never felt like this about another guy before."

Karen paused, then just said, "I'll think about it, honey."

The next day, Karen and Jack were out to lunch when Karen decided to bring up the subject of her brother. Conner was seeing a movie with Will and Grace and Karen worried that she wouldn't have another chance to get Jack alone.

"Honey, what do you think of Conner?" she asked him.

"He's nice, good dresser, obviously inherited his good looks from his sister," Jack replied, winking at Karen. She smiled.

"But, would you go out with him? If he asked you? And not just a one-nighter, Jackie, I mean really go out with him, see how much you like him, maybe forge an actual relationship," she explained.

"Hey, I am excellent with commitment, I had 5 serious relationships going at once one time," Jack defended himself. "And, I suppose if I like Conner enough, sidebar: which I do, I'd go out with him. Why?"

"Oh, no reason, honey," Karen replied. "I was just curious."

Jack raised an eyebrow.

"Karen...," he began.

"Alright, alright, Conner's in love with you!" she exclaimed. She took a big drink from her glass as Jack contemplated this. Then she continued. "I mean, he likes you a lot and thinks he's in love with you and he wants to go out with you. But he wants my permission first."

"And did you give it to him?" Jack asked.

"Well, not yet, I told him I'd think about it. I mean, you're both so dear to me, if you did have a relationship but something happened and you broke up, who would I comfort? You're my best friend and he's my little brother," Karen said. "Plus, well, Conner's rather new to this and you're...more experienced."

Jack leaned back in his chair and thought about it. Finally, he looked at Karen and said seriously, "If you did give Conner permission, I'd do my best not to hurt him. Now, I'm not saying we'll become an exclusive couple, but I promise if I don't see us being anything more than good friends, I'll let him down as easily and gently as possible. And if we do become a couple and we break up, I'll fully understand if you feel the need to comfort him first."

"Aw, thanks poodle," Karen said, rather doubtful about the last part but happy that Jack was willing to give it a shot. "I guess I'll tell Conner that he's free to go out with you."

When Jack and Karen returned to work, Conner and Grace were there waiting for them. Conner quickly took Karen aside.

"Well?" he asked expectantly.

Karen sighed, hoping she was doing the right thing, and nodded.

"Go ahead darling," she replied. She handed Conner a few twenty dollar bills. "Go someplace nice, and this is Jack we're talking about, so be prepared to pay for everything."

"Thanks, sis," Conner said, kissing her quickly on the cheek before hurrying over to Jack. The minute Jack turned around, Conner said, "Jack, would you like to go out to dinner with me tonight?"

Jack paused and looked at Karen, who quickly busied herself by concentrating on powdering her face, then at Grace, who pretended to be immersed in a collection of different wallpapers. He then looked back at Conner and smiled.

"I'd love to," he replied.

Ever the gentleman, Conner took Jack's arm in his and the two left for a night on the town.

That night, Karen waited nervously in the longue for Jack and Conner to return. She didn't know what to hope for. If things went well, maybe Jack and Conner could become a couple and Conner could move to New York. But if they broke up, Karen worried about who she would have to comfort and whether the other one would be upset with her choice. On the other hand, if things didn't work out, she worried how Conner might feel.

The hours crept past and soon Karen had fallen asleep on the love seat. But she awoke the minute she heard Conner's key in the door. He and Jack entered and Karen decided to keep still and pretend to be asleep.

"Well, I had fun tonight, Jack," Conner said.

"Yeah, I'm sorry it didn't work out," Jack said. Karen felt a pang in her chest and glanced at her brother through slitted eyes, wondering what he was feeling. But she was surprised to see that he actually looked like he was smiling.

"Yeah, but at least we took a chance and found out," Conner said.

"And you did get the phone number of that guy," Jack pointed out. Conner blushed.

"Yeah," he admitted. "Thanks to you inadvertently knocking me into him at the bar."

He and Jack laughed, then quickly hugged.

"I'll see you tomorrow," Jack said.

"Bye Jack," Conner replied.

Karen smiled to herself as Jack left the Walker residence. She was so relieved at how well things had gone. She lay still, waiting for Conner to return to his room so that she could return to hers. Conner paused before going down the hall.

"Goodnight, Karen," he said.

Karen sat up and looked at her little brother. He was grinning at her and she smiled back.

"Goodnight, Conner," she replied.

Epilogue:

The next day, Conner met Jack and Karen at Grace's office. They left soon after and went on a shopping spree. They bought Conner a whole new wardrobe, then went looking at apartments. Conner was planning on moving to New York to be closer to his sister and Jack and all the clubs. Karen felt incredibly lucky to have the two most wonderful men in her life right by her side.

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