Nate had a date. A hot date no less, a girl from his Philosophy class at Columbia. She was blond with blue eyes and big boobs. It was time to get back in the saddle. Being alone was completely overrated.

He straightened his collar and admired himself in the mirror. Pretty hot. He thought to himself. He checked his watch and went to grab his keys. Sure he'd told his grandfather that he was giving the Ferrari back but then he figured that keeping it for a couple weeks couldn't hurt. Besides if they didn't want to speak to him how could his family ask for it back?

"Nice car." His date, Serenity, said when he picked her up. "What is it like a Rolls Royce or something?" Nate tried not to roll his eyes at her.

"It's a Ferrari actually. My grandfather gave it to me, perhaps you've heard of him. William Vanderbilt." Nate usually didn't name drop but he was in the mood to impress.

"My dad does business with him." She said. "He's thinks very highly of him." She slid into the passenger seat of the car, giving him a preview of what was under her skirt in the process. Nate winked at her.

Three hours later Nate was trying to remember why he had asked Serenity out in the first place. Sure she was nice to look at but there was a lot missing upstairs. She'd spent the first hour talking about her new dog. A Teacup Poodle named Sylvester. Apparently after Sylvester Stallone, who was her favorite hairdresser. Nate was bored.

"Oh! Hello, it's my favorite magazine. Just a second I have to see what's happening in the world." Serenity said grabbing the magazine and leafing through it. "It's so important to be up on the issues of the world today." She told Nate matter-of-factually. He nodded.

"Good grief why doesn't she just hire a photographer to follow her everywhere? She's all over now what's so great about her." Serenity wrinkled her nose in disgust. "Ugh Serena van der Woodsen, so over rated." Nate's head shot up at the mention of her name.

"What does it say about her?" Nate asked trying to be non-chalent. "She was out at some club opening with Shia LaBeouf last night. Look, what an attention whore." Nate practically grabbed the magazine out of the girl's hands.

His heart practically stopped at the sight of Serena's smiling face as she danced with what's his face from Transformers. The picture barely did her justice.

"Hey, Nate!" Serenity was getting impatient. "We're on a date not you and some over photographed debutard. Ugh, she's not even pretty."

"She's gorgeous and she's fun and she's wonderful." Nate snapped. "Tell you what why don't you catch a cab." He handed her a 20 dollar bill. "I just don't think it's going to work out between us." He turned to walk away.

"Yeah well." She stopped as she tried to think of a retort but by then Nate was out of earshot.

"Archibald." Carter said emerging from the Club's bar area. "I was hoping to meet you here." Nate barely acknowledged him.

"Carter what can I do for you? Serena's favorite color? Which kind of underwear she prefers? Her turn ons perhaps?" Nate sipped his whiskey sour and turned to face the older boy. Carter's face was arranged in a scowl.

"I have no problem turning on my girlfriend and as for her underwear…well let's just say that she rarely worries about losing it." Carter smirked knowing he had hit a button. Nate tried to ignore the images of Carter and Serena invading his mind. "Actually I wanted to give you a little friendly advice. Man to man."

"Oh and what could you possible have to advise me on?" Nate shot back. "Manipulation? Lying? Cheating? Stealing? Shaming your family?"

"Funny last I checked my family had welcomed me back with open arms and yours was still ignoring your calls." Carter retorted moving closer to Nate. "My advice is that you keep your hands to yourself when it comes to Serena." Their faces were inches apart and Nate was not about to back down from Carter Baizen.

"Serena's a big girl she can make her own decisions." Nate countered.

"True. I'm not choosing for her just offering some friendly advice. Besides I spent last night with her I'm not worried." Carter moved away towards the exit.

"If you're not worried then why are you threatening me?" Nate challenged.

"Because there's nothing wrong with a little insurance." Carter shot back. "We had a deal Archibald and I can always do the opposite. Tell grandfather Vanderbilt about the gambling and partying. That might not go over so well. Or I could tell Serena that you made a deal with me."

"Won't that make her mad her you?" Nate asked.

"No, I'll tell her that I was simply nervous about making her happy but you demanded that I do you a favor in return. I simply wanted some friendly advice." Carter smirked. "Have a good night Archibald. I'm going to go see my girlfriend. I hear that Rufus is treating Lily, Eric, and Jenny to a night out at the theatre. So we'll be all alone." With that Carter left and Nate had to take a deep breath to keep from smashing his drink glass in his fist.