A/N: I know you guys liked the fluff, but we can't have fluff for too long, right? A little bit of a curveball and some foreshadowing. Let me know what you guys think, and feel free to throw out some theories! It may be a while before I release the second half of this storyline in the next chapter, since I've been quite busy lately. As usual, thanks for the lovely feedback from my dear faithful readers!

"Soooo what are we doing tonight?" Seth asked, sliding up to Blair as she was closing her locker.

"I am spending some girl time with Summer tonight, since I promised her a week ago that I would help her with her algebra, so we aren't doing anything," Blair replied. She turned around to face her boyfriend, tiptoeing to greet him with a soft peck on his cheek.

Seth groaned. He was glad that Blair and Summer were getting along so well despite his history with the both of them, but he didn't really enjoy having to share his girlfriend all the time. He had been looking forward to spending a night in with Blair, just watching a movie – or three. "Blair, I swear last week it was you who was complaining about not having enough alone time," he pointed out with a slight pout.

Blair reached up and ruffled his hair affectionately. "Oh, boyfriend, don't be jealous. I promise I'll make it up to you this weekend," she teased, leaning in closer to him, her nose touching his ever-so-slightly. Seth also leaned in a little closer and wrapped his arms around her waist. Their lips were just about to meet when they were suddenly interrupted by the sound of Summer's voice right beside them.

"Ew," she complained, prompting the startled couple to take a step back, "get a room, you two!" She stepped in between the two of them and grabbed Blair by the arm. "So Waldorf, are we still on for tonight?"

Blair was looking longingly at Seth, but snapped out of it as soon as Summer approached her. She opened her eyes wide and plastered a smile on her face. "Summer!" she exclaimed in false excitement. "Uh…yes. My place at seven?"

"Sure. Ooooh! We can watch The Valley first, and study at the same time! Can't wait! Catch you later, B!" She waved casually at Blair then walked away, throwing one last disgusted look at Seth before she left.

Blair maintained her smile until Summer disappeared around the corner. "Did she just call me B? No one calls me B but Serena, and I am not calling her S!" she seethed, still looking in Summer's direction.

"I thought you wanted to be nice to her," Seth reminded, though equally agitated by the way Summer had interrupted their little moment. He leaned against the locker, watching Blair's expression. "I know that look. What are you thinking, Blair?" he asked cautiously.

Blair turned to him, a small twinkle in her eye. "There's only one way to get rid of her, Seth," she started, a smile playing upon her lips.

"You want to cut her up to pieces and feed them to your neighbour's yappity Chihuahua?" Seth asked, wrinkling his nose.

Blair rolled her eyes at him. "No Seth, though I guess that would kill two birds." She suddenly turned serious. "We're gonna find her a boyfriend," she announced dramatically.

Seth lifted an eyebrow doubtfully. "You really think it'll be that easy to find someone to replace me? I mean, I'm pretty hard to get over," he joked.

Blair hit him with her purse and laughed. "Shut up, Cohen! I mean it! It'll be the perfect way to get her off both our backs, and we'll have all the time in the world to spend with each other," she emphasized, smiling sweetly at him.

Seth couldn't help but return the smile, his dimple appearing deeply in his cheek. He held on to Blair's hand, and swung it from left to right as they spoke. "Yes, yes. You're right, as always. But it's Summer we're talking about. She isn't exactly the easiest girl to please."

"Is that yet another attempt to fish for a compliment? 'Cause your ego is getting so big I can hardly breathe in here," she teased matter-of-factly.

"Do you have any suggestions?" Seth asked. They both leaned against the locker and observed the flock of boys that were making their way down Harbor's halls.

Blair watched as two boys walked past them, one of them dribbling a basketball. He had light brown hair, and thick eyebrows. Kind of reminded her of Nate, but more…sweaty. "This one? Sporty…nice face," Blair commented.

"…and a complete douche. He looks like he hasn't washed his hair in two months," Seth complained. Blair shrugged. The man had a point.

Seth suddenly nudged Blair with his elbow. "Oh oh ooooh! That one! He looks like the smart and sensitive type," he said as he nodded approvingly at a band member that walked past them with a French Horn in his hands. He had on thick-rimmed glasses and the tightest pants Blair had ever seen anyone wear – boy or girl.

"You cannot be serious," Blair replied with a disgusted look on her face. She scanned the hall for another suitable candidate. "That one over there?" she suggested, nodding in the direction of an Asian boy dressed in a yellow preppy sweater.

"Blair, my grandfather has that sweater." Seth looked over at Blair as she tried to hide her smirk. "I'd have to say you have the absolute worst taste in men," Seth answered, shaking his head.

"Which explains what I'm doing with you," she answered lightly. "What do you know about what girls want, anyway?"

Seth rewarded her with an adoring smile for her snarky comment, and Blair narrowed her eyes playfully at him. "I know what they don't want, and that's Mr. Asian Sensation there who looks as if he's spent the last ten years of his life playing golf with the guy from The Price is Right," he retorted.

"Well, fine then," Blair conceded, "I hereby challenge you to a duel. One week. To find the most suitable date for Summer – one that she would approve of and be happy with. You in?"

"A duel? Blair, you want to fight me…with swords and other advanced weaponry?" he joked.

"Is that fear I hear hidden behind your little Jewish sarcasm, Cohen?" Blair cooed at him.

Seth mimed an exaggerated laugh. "Oh you're going down, Waldorf. Don't cry to me when you realize that Seth Cohen is actually the single most badass matchmaker in town. Might even go ahead and start my own business. Tell you what, Blair. To prove how non-scared I am of your little challenge, I will give you a head start and allow you to pick your man first to take Summer out on a date. Consider it my gift for you, because you're my girlfriend," he replied, crossing his arms.

"You're going to be sorry, Seth. No one wins a challenge like Blair Waldorf," she warned, walking away from him.

"We'll see about that," he called out behind her. Blair smiled victoriously to herself. She had no doubt that she would be able to find the most suitable guy for Summer. After all, all girls in Newport wanted a variation of the same thing – rich and handsome, smart and sensitive. Maybe not so much smart, for Summer, because let's be honest – her intelligence is not exactly her forte. She whistled to herself as she continued to keep her eyes peeled for the task, and made a mental note to assign her minions to go through the entire Harbor database and come up with a list of all the eligible bachelors by sundown. Just when she was about to dial Kelly's number, she was interrupted by a husky voice:

"Blair? How've you been?"

Blair looked up – way up – and saw Luke Ward staring down at her. He was wearing a sleeveless shirt which showed off his bulging biceps despite it being the middle of winter, and she had to admit that he was looking better than ever. He ran his hand through his dirty blonde hair, and she examined him closely while one of his friends passed by, punching him playfully on his arm.

Hmm…rich, categorically handsome, impeccably sensitive…and as a bonus, definitely popular, Blair thought. True, he may not be her type, but she knew that Luke was certainly considered a good catch in just about every other girl's eyes. As for the intelligence department – well, she had already established that it wouldn't be necessary for Summer, so why not?

"Luke!" she exclaimed brightly. "Just the boy I wanted to see!"

"Really?" Luke wondered aloud, looking surprised.

Blair didn't want to encourage him, but she had her mind set on him from the moment he magically appeared in front of her two minutes ago, and she took it as a sign of divine intervention. Besides, pairing Summer up with Luke would single-handedly resolve both of their residual feelings for Seth and Blair respectively, and would effectively displace them to a new, more appropriate, target. It was like killing ten birds with one stone. Blair smiled to herself in satisfaction.

"So Luke, are you free this Friday night?" Blair asked, batting her eyelashes at him innocently while they walked down the halls together.

Seth shifted uncomfortably in his seat. From the moment he learned that the "ideal date" Blair had chosen was Luke, he had known that this would be a horrible idea. But of course, when Blair Waldorf had her heart set on something, there was no telling her otherwise. He stabbed at his plate of salad grumpily.

"Seth, mind your manners," Blair said to him through her teeth. She knew that this wasn't the most desirable arrangement with her and Seth out on a double date with Luke and Summer, but she had chosen the fanciest, most exclusive restaurant in Newport, and was confident that if nothing else, the romantic ambience should put everyone on the right track. The truth was, Blair didn't know how else to get Summer to agree to go on a date with Luke without masking it as just a casual dinner with the two of them. She prayed for the best as the four of them picked at their salads awkwardly, no one making a sound. Blair decided to take action. "Soooo Luke, why don't you tell everyone about the new convertible your dad just got you, huh?" Blair prodded him, trying to make conversation.

"Um…I can't figure out how to drive stick, so he got me an automatic," Luke answered straightforwardly. Blair caught Summer rolling her eyes at him, and Luke continued to look at his plate uncomfortably. She felt bad for dragging him into this, especially while getting his hopes up by leading him to think that she wanted to have dinner with him alone, but convinced herself that it was all for a greater good. Unsure of what else to say, she nudged Seth sharply in the ribs. "Say something, Cohen!" she whispered at him.

"It's a competition!" he whispered back, both of them disappearing under the table. Blair shot him a menacing glare, which Seth ignored, and the both of them sat up straight again, rejoining the table. Summer was looking distractedly at the tables around them, as she realized that they were the only ones in the entire restaurant.

"Why is this place so empty? I thought it was a Michelin three-star," Summer asked curiously.

"It is," Blair chimed in, relieved that there was finally something to talk about, "I reserved the entire place for us tonight. I wanted a quiet and cozy environment for all of us to get to know each other." Blair looked meaningfully at Summer and Luke, who shared an awkward glance. Summer looked away immediately, as if afraid to catch Luke's eyes. "So," Blair attempted again, "Summer, why don't you tell us about how you and Luke know each other?"

Summer made a face at her. "We hardly do. I only know him because he dated Coop for like, their entire prepubescent lives," she pointed out.

Oops. Blair hadn't considered that before deciding on the plan. She had only figured that Summer would at least find some redeeming qualities in Luke, since Blair had honestly begun seeing him in a new, much more favorable light right before Seth suddenly kissed her on the night of the school play. The thought of it sent a light blush to Blair's cheeks.

Luke observed Blair's reaction, and suddenly spoke up. "Well, I always thought you were a cool girl, even when I was dating Marissa," he offered, realizing what Blair was trying to do and attempting to be cooperative for her sake. He gave her a friendly smile, which made Summer smile back, after some hesitation.

"Thanks," she replied, "you too – I guess." They looked at each other and exchanged another small smile.

"GREAT!" Blair exclaimed a little too happily, clapping her hands together. "Shall we fetch the maître d' and ask for our entrees? You've got to try a bit of my Canard à la Rouennaise – it's simply divine," Blair gushed at Seth. She proceeded to wave the waiter over and conversed with him in fluent French.

Seth sank back into the chair. He always wondered why these fine dining places always had such uncomfortable seats, as if they were worried that sitting comfortably might give you bad posture. It's not that he never ate out at such fancy restaurants; being a Cohen, he was accustomed to being pulled along to having long, boring family gatherings at the most snobby and pretentious of places. Still, he found it unsettling that this was Blair's idea of a perfect date, looking perfectly content and right at home, while Seth wanted nothing more than to curl up on his couch and relax in front of his video games. He watched as Summer and Luke began to chat with one another, making small talk.

By the end of the night, it seemed that Summer and Luke were getting along just fine, and Luke had even managed to make Summer laugh out loud a few times. Granted, Seth thought Luke's jokes were merely a grade up from knock-knock jokes, but who was he to judge? He was just dying to get back home at this point and completely write the day off. Luke had kindly offered to drive Summer home, and Seth eagerly rushed back to his car to take Blair.

Blair was humming cheerfully to herself while Seth drove in silence. "Well I'd say that went rather well, wouldn't you?" she asked him, not waiting for an answer. "I just knew they would hit it off!"

"I wouldn't exactly say they hit it off," Seth remarked, "but sure, if you say so." He continued driving, not in the mood to elaborate. Blair watched him curiously, surprised at his sullen mood. It wasn't like Seth to be so quiet. Usually, he wouldn't stop talking even when she demanded for him to shut it.

"Does this have to do with the fact that you don't approve of Luke?" Blair suggested, slightly annoyed that Seth was being such a sore loser.

"It's not about that. Just – forget about it, okay?" Seth replied. He was trying to concentrate on the road, but something was upsetting him – something he couldn't quite put his finger on.

"Is it because you don't want Summer to start dating? Are you jealous, Cohen?" Blair asked, throwing out random theories now. She didn't like that he was acting so cold to her, especially when she was in such a good mood over the seemingly successful date.

"No, Blair! I said just leave it, okay?"

They drove the rest of the way in silence, and Seth opened the door for Blair as she got out of the car. Without turning back to look at him, Blair walked into her house and shut the door behind her. Seth got back into the driver's seat and sighed. He knew that Blair would inevitably be upset at him for a day or two after tonight, but he really wasn't in the mood to explain to her. Besides, he had no idea what he would explain, even if he wanted to. It seemed that the evening had simply caused a wave of melancholy to wash over him, and he was left with an unsettling feeling at the pit of his stomach. Maybe Blair was right, he thought. Maybe he was just upset at the fact that he seemed to have lost after Summer and Luke's date, and was just nervous about the fact that he hadn't found any suitable candidates for her yet.

Feeling moody after the strange double date and his non-fight with Blair, Seth decided to drive out to the beach to get some fresh air. Just as he was stepping out onto his skateboard to ride towards the beach, he crashed head-on into a stranger dressed in a purple blazer and light pink shirt. Even under the low light, he could see how new and crisp his shirt looked. He stepped back, rubbing his head at the collision and taking some time to examine the other victim. The boy looked around his age, maybe one or two years older, though it was difficult to tell with all that hair gel and his strange attire. Who wears purple blazers in Newport? Seth wondered to himself.

"Are you alright? Sorry I didn't see you there," Seth explained, helping the stranger catch his balance.

The boy held out his arm, signaling that he was fine. Almost immediately, two extremely tall and skinny model lookalikes rushed up to him, each taking him by one arm. "I'm fine, ladies," he assured them, looking at them with an air of arrogance that Seth thought only appeared in movies like The Godfather. "You should check if this one is okay instead," he said, throwing his head in Seth's direction.

The girls obediently headed towards Seth instead, but he stopped them before they could touch him. "I'm fine, really. This happens to me all the time," Seth replied in attempt to lighten the mood. The stranger continued to stand at an awkwardly straight angle, examining his polished Berluti's for scratches. Just the sight of him radiated money – and not just the regular Newport kind. Seth knew at a glance that this guy was completely loaded. What's more, he was also a complete womanizer. He watched in awe as the supermodels approached him again, appearing to be wholly at his command. He glared at the two of them, then looked up at Seth, realizing that he was still there and was watching him intently.

"Is there a problem?" the stranger asked rather sharply.

Seth gulped loudly. "Well…no. Actually yes – I mean, no. Not a problem," Seth stuttered. He took a deep breath to gather his thoughts. "What I'm trying to say is, I was wondering whether you'd be interested in a date," he finally managed.

"A date?" the boy almost spat the words out. "You want to ask me out on a date? Sorry, but I don't think you're my type," he replied, looking slightly amused at this point.

"Oh, you thought I meant me? Oh, wow, um – no, although I now see how that question could have been grossly misinterpreted. But no, that – uh….no," he finally finished. The stranger looked at Seth impatiently. Seth drew in a deep breath and started again. "What I meant was, there's this really nice girl that I've been wanting to find a date for, and it would nice if you can take her out on a date. That is – if you're free," he explained.

"Interesting," the boy growled in a low voice, waving away his companions and leaning in closer towards Seth. "So tell me, if this girl is really so nice, why does she need you to try to get her a date?"

Seth suddenly realized why he was so drawn to this stranger – he reminded him oddly of Batman, with his low whispers and the way he openly flashed his wealth and status. "She doesn't," he replied, seeing that he was pretty much trying to do the impossible. "It's kind of a bet that I made with my girlfriend, and we were both trying to find the best date for our friend. She found someone, and now it's my turn," Seth informed him unwillingly, realizing how utterly twisted and pathetic the whole thing sounded.

"Now it makes sense," the stranger replied.

"It does?" Seth didn't think it made any sense at all.

"Of course it does. You want to find the best of the best to beat your girlfriend, and you found me, who you assumed would be able to win this girl's heart since I'm obviously rich, charming, and have my way with all sorts of women," he replied cockily, giving him a sneer.

Seth didn't realize that anyone could speak with such an air of superiority, and wasn't sure whether he should feel humbled or disgusted by the size of this guy's ego. It wasn't usually his type, but he remembered Blair telling him that girls loved confidence – and this guy was sure as hell confident. "So, are you in?" he asked, half-hoping that he would say no.

"Sure, why not? I have a week to kill before flying back home anyway," he replied, holding out his hand.

"I'm Chuck Bass."