A/N: Kind of ties in with my story, KindaSortaMaybe, but you don't have to read that to understand this. It's probably good if you at least read the Characters chapter in KindaSortaMaybe. Otherwise, the OC's might confuse you. AU-ish.

What is the best way to propose, anyway? Honestly, girls were picky. Of course, that didn't stop millions of proposals from happening every day. Sometimes, it ended in happy tears and kisses. Other times, it ended in broken hearts and awkward rejections. In retrospect, Jack probably was just part of another one of the millions of proposals that happened every day. He had hoped for a quiet, quaint little proposal where Kim would say "yes" right away, but he supposed that would be asking for too much. Therefore, on February 14th, when Jack Anderson walked out of his large mansion, and into the road, he was expecting not a peaceful proposal, but at least a successful one. You see, Jack Anderson is a whispered, revered name among CIA teen spies. Jack Anderson is also a name that's very popular in magazines. Of course, the title of Oscar (three times) and Grammy (one) winner had something to do with that, not to mention being the son of a famous model (and a pretty respectable model himself). He wasn't the only one with such prestige. His close friends, each and every one of them, all operated within the same circle as him. Jerry Martinez, Kelsi soon-to-be Martinez, Eddie and Amanda used-to-be-Bryant McCornick, Rachel formerly-Young and Milton Krupnick, Wini married-happily and Andrew Flarhety, Fawn forced-to-marry (or so was her excuse) and Drew Shawn, and Thomas and Cora I-don't-like-this-last-name Condor were just a few of the highly revered, highly publicized names that were Jack's best friends. And, of course, there was one more, veryveryvery special person that made today a veryveryvery important day for Jack Anderson.

"Hey, Jack!"

Kim Crawford, model and singer extraordinaire (three Grammys, thank you very much). Throw in a few movies (one Oscar) and you've got yourself a triple threat. Also known as, Jack's longtime girlfriend. They got together when they were 15, and 8 years later, were still going strong. Although, today was the day that Jack might have the honor of changing Kim Crawford's last name.

"Hi, Kim," replied Jack, kissing her on the cheek. "Hey, listen, the guys and I are having brunch at Kerry's Cafe, so can I catch up with you later?"

"Actually, that's perfect. I have to go to brunch with the girls, too, and Nate's going to drop me off," explained the lovely blond.

Jack paused. "Nate Effenhowser?" Being girlfriend/boyfriend for ten years leaves you with the ability to read the other like a book. Kim Crawford and Jack Anderson were no exception to this very ancient law.

Kim smiled, leaning up (because eight years later, Jack still held five inches over her) to kiss him soundly on the lips. Pulling away, she replied, "Jack. He's just a friend."

"Just a friend, my ass," said Jack half-heartedly. "Did you not see him totally checking you out?"

"Careful, Jack, you're starting to sound like Cora," chided Kim, referring to her crazy, flirty best friend. Actually, shorten that to crazy. Thomas is cute when he's jealous, but such a pain, too.

"Whatever," grumbled Jack. "I still don't like him."

"Aw, Jack, you're cute when you're jealous," giggled Kim. She patted his shoulder. "C'mon, how long have we been together?"

"Eight years, five months, six days and counting," replied Jack promptly.

Different emotions flickered over her face. Shock, disbelief, then a tender love. "Oh my, God, Jack, you counted the days?"

He grinned sheepishly back at her. "I'm not much of a romantic, but I pulled straight A's in math."

Kim shoved his shoulder. "Way to ruin a romantic moment, you jerk."

"You love this jerk," he replied, pulling her into a hug. He dipped her, and kissed her soundly.

"Jack," she murmured. "We're in the middle of the sidewalk. People are staring."

He smirked against her lips. "Let them. They're just jealous."

Kim laughed breathlessly, pulling away. "I really have to go, but I'll see you later, okay?"

"Bye, Princess," he mumbled, kissing her one last time.

"See ya later, Casablanca."

-Kickin It With You!-

"Hey, Thomas," Jack greeted the blond. "How's Cora?"

Thomas rolled his eyes. "Three months pregnant. She's annoying the hell outta me!" he whined, to which Eddie, entering, the cafe, just chuckled.

"Yeah, well, get used to it. Believe me, it gets worse," reassured Eddie.

Andrew, catching the tail end of their conversation, added, "When Wini was pregnant, she kept asking for these weird choco-bananna sandwiches."

Drew walked in, groaning. "Do not mention pregnancy to me. Seriously. Andrew, whatever Wini did, she can't be half as bad as Fawn. She kept throwing staplers at my head the whole entire time and making me buy her weird food. The whole. Entire. Time. Do you guys realize how long that is?"

"Nine months," replied Milton promptly, ever the genius.

"Hey, guys!" chirped Jerry, walking in cheerfully.

"Why are you so happy?" muttered Thomas.

Jack rolled his eyes at his friend's antics. "He's just happy that he's getting married."

"Two more months, baby!" crowed Jerry.

"Hey, speaking of getting married, how come you and Kim aren't hitched yet?" asked Eddie.

Jack groaned, letting his head fall in between his hands. "You know I've tried to propose a million times. I've used every trick in the book, and some that aren't in the book!"

-Flashback-

"A toast," said Jack, raising his glass to Kim. "To the most important woman of my life."

Kim blushed. Jack was kind of goofy and fun most of the time, so whenever he got romantic, she got flustered. "Thanks, Jack," She raised the glass to her lips and drank. And promptly choked. Jack would later thank Mr. Jackson personally for teaching the Heimlich Maneuver in eight grade gym class.

Throughout the chaos that ensued, Kim never remembered to ask what it was that made her choke. She never knew that Jack was trying to propose, and what she choked on was actually a ring.

-Flashback Over-

Drew chortled. "Oh, God, I remember that!"

"That was a fail," Jack deadpanned.

"Or what about the time you put the ring in her cake?" laughed Andrew.

Milton grinned. "Kim choked. Again."

"You know, you really should send Mr. Jackson more muffin baskets," Jerry mused.

"You know, I did try proposing to her through fireworks," Jack muttered.

Eddie's eyes widened. "I remember that! You had millions of Kims calling you that day because they thought you proposed to them!"

"Kim was sick that day," said Jack glumly.

"Do you guys remember the time he tried doing it with one of those airplane cloud thingies?" asked Thomas.

Jack groaned. "A stupid airplane flew over it. The message was completely destroyed."

Andrew shook his head, whistling. "You know, you seem to have it the hardest. It surprises us all, you know?"

"Yeah," agreed Milton. "We though you'd be the first one to get hitched."

"And now, we're all on our way to a family life." Eddie shook his head. "It really is ironic."

"Anyway, I'm gonna propose to her today," announced Jack.

Milton snickered. "Yeah. Again."

Jack glared at him. "Shut up, Milton. Besides, all those times weren't really my fault..."

Thomas and Drew looked at each other, then chorused, "It was karma."

Jack waved them away. "Not helping, guys. C'mon, help me out! It has to work this time!"

"Speaking of, I wonder how many rings and how much money you spent trying to propose to her," mused Jerry.

Jack actually considered it for a second, then waved his question away. "Money, I've got plenty of. I just need it to work, this one time!"

Jerry, however, was not letting it go, and was counting on his fingers. "Let's see, that time, plus that other time, and, oh, those times..."

Impatiently, Milton answered. "Jack tried to propose six times. Six rings. I'm guessing... $300,000?"

Jack nodded glumly. "Something like that."

Drew whistled. "Just on rings alone."

Andrew grew tired of the constant flamboyant proposals, and suggested, "Why not just propose to her normally? That's what I did with Wini. You know, take her to a romantic place, have dinner, get down on one knee."

"Yes! That's it! I'll propose to her normally!" Jack looked delighted. He quickly reached for his iPhone. "Hey, Yvette. Book me a private conference room for two at New York's best resturant. Six o' clock. Yep. Uh-huh. Thanks."

He grinned at the seven guys assembled in the flowery cafe. "Wow, you all have way too much time on your hands."

-Kickin' It With You!-

"Hey!" greeted Kim breathlessly.

"Hi, Kim," said Cora, hugging her best friend. "Everyone's waiting for you."

The second Kim stepped into the living room, she was bombarded with questions.

"So, who was the cutie who dropped you off?" Kelsi wanted to know.

"I don't think it was Jack!" sing-songed Fawn.

"Uh-oh, trouble in paradise?" teased Amanda.

Rachel gasped theatrically. "I think the golden couple is turning bronze!"

"That doesn't make sense," Wini deadpanned. "Hi, Kim. Sorry you had to be here with all these crazies. Don't worry, they took their meds. I think."

"Wini, just because you're two weeks pregnant with your second kid doesn't mean you're helpless," Kelsi pointed out. "So we could totally attack right now and not get yelled at by Andrew. Actually, he would probably encourage it. After all, he's going to be taking care of you for the next nine months."

"Yeah, you guys really got busy after you got hitched!" crowed Cora, winking at Wini. "So, how's Andrew in bed?"

"Cora!" Amanda let out a scandalized hiss.

Cora waved her away, laughing. "Jk, honey, jk. Besides, I hear you and Eddie are pretty busy yourselves. How are the Twin Terrors these days?"

Amanda smiled grimly. "Annoying the hell outta me, but looking adorable doing it."

"Kimmy, you have got to get married!" pleaded Amanda desperately. "Otherwise I'll be forced to arrange play dates with Fawn, Wini, or Cora's children. You know, if you stay around crazies for too long, you might become one of them."

"I only see one crazy in the room, and that's Kim," proclaimed Rachel. "Seriously, honey, either get married or dump the guy!"

Kelsi evidently agreed. "I mean, Jack's hot and all, but it's been 8 years. If the kid doesn't plan on marrying you soon, then you're better off with Cutie from before."

"Speaking of, who was that?" wondered Fawn.

"Nate Effenhowser. I mentioned he was bringing me here to Jack this morning, and he got all jealous," explained Kim. "And you know what? He counted the days that we've been together!"

"That's sweet, but when is the boy going to propose?" snapped Fawn impatiently. "Seriously, Kim, we all love Jackie-boy, but this is getting ridiculous."

Kim hesitated before answering. "Jack will propose when he's ready."

"Well, he better be ready soon," muttered Wini. "Or the crazies- that's us, by the way- are gonna go after him."

-Kickin' It With You-

Halfway across town, Jack was picking up a ring from the best jewelry store in the city, when he felt a chill go down his spine. Was that a spark of malicious intent?