A/N: There was so much potential in Nate and Jenny, don't you think? I started planning a multi chapter fic with them a while ago, but in between figuring out stories and plots I started to play around with other pairings that might come between them, and thus, this fic was born! It might be a rough ride for a while, but stay with me guys. Nobody ships Nate and Jenny harder than I do! Although I do love my angst in fanfic... Enjoy! x


Friends and Benefits

She'd never been more grateful that Gossip Girl was dead and gone. Or, at least, that 'she' was no longer chronicling her life. Jenny had to give credit where credit was due – she and her brother had pulled off one of the biggest schemes in UES history, and while she'd sabotaged herself one too many times, she had to admit that the likelihood of her life turning out the way it had had a lot to do with who she was in high school. If she'd never gone to Constance, she wouldn't have become the brave young woman she was. She would never have gone toe to toe with Blair Waldorf and won, and she never would have been able to call Blair a friend.

Sure, they'd had their issues. On occasion, they still had their issues. But the loathing between them was hidden away in a Louis Vuitton somewhere in Blair's attic and that was where it was going to stay. Now they were friends, colleagues – business partners. Successful ones at that.

'What time is it?' her… friend asked from beneath the duvet. The top of his brown hair was peeping out and Jenny affectionately ran her fingers through it. It was one of her favourite things about him, of which there were many.

'Later than we'd like,' Jenny told him.

As she pulled the covers back to reveal him in his boxers, she thought about what they were exactly. They'd only reconnected a few months ago, and she used that term loosely because they were never really anything anyway. He'd spent one breakfast with her extended family years ago, and she'd seen him for the first time a couple of years before that at Serena and Blair's cotillion. That was it.

Of all the places in the world, London was where they'd met again.

Stressed, frazzled, furious and several other things at once, Jenny had been in a hurry to get home and finish packing for her trip to Italy on behalf of Waldorf Designs. Fabrics were missing, another shipment had gone rogue and Blair was breathing down her neck to get some fresh ideas on the table by the time she came back to Manhattan. Jenny hadn't even seen the leggy blonde heading her way on the arm of an up and coming entrepreneur. Before she could side step the girl, Jenny had careered right into her and they fell to the ground in a crumpled heap.

Hissing in pain, Jenny examined the cut on her knee exasperatedly. There goes the mini dress for the cocktail reception tonight, she thought. Accepting the hand that was offered to her, Jenny was helped to her feet, still in one piece. Her phone, on the other hand, was in several pieces and the strap of her handbag had broken. Cursing, Jenny picked up the fragments of her iPhone and attempted to put it back together to no avail.

'I'm sorry, we didn't see you,' the entrepreneur said with an apologetic smile as he helped his date to her feet, too.

'Don't worry about it,' Jenny said. 'I should have been paying attention.'

She chose this moment to look up and found a familiar face looking back.

'I know you,' they said in unison, and he smiled.

'Carter Baizen.' Jenny offered a small smile, given the circumstances. He'd never been very well liked among her friends and family, and though she didn't know him personally, she'd heard enough to know she should probably stay away.

'And you are…' he began, struggling a little. Jenny raised her eyebrows, but didn't offer any help. If he remembered her at all then surely he could dig a little deeper and pull out her name. 'Dan's sister.'

Jenny rolled her eyes. She'd grown up being Dan's sister, but she was so much more than just that now. Still, at least he'd tried. 'Jenny Humphrey,' she informed him, somewhat sharply.

'My bad,' he said. He spied the J for Waldorf design on her handbag and it seemed to dawn on him that she was still a part of the Upper East Side. 'I remember Blair telling me about you during out brief – albeit fun – rendezvous.'

Jenny crinkled her nose in disgust for his date, and she looked quickly at the blonde. She was standing, appropriately, off to the side like a spare part, waiting. Jenny felt for her; she'd been that girl before. Waiting for the guy to notice her, or just remember she was there. Only one guy had ever really made her feel that way, but she hadn't seen him in a few years.

She snapped back to her conversation.

'I should go,' she said, sparing another glance for Carter's date. 'Let you get back to… I'm sorry, what's your name?'

'Tabitha,' the girl offered abruptly, stepping forward and sliding her arm through Carter's.

Despite this, his gaze seemed fixed on Jenny and she couldn't deny it felt a little good. Tabitha was stunning. Long legs, high heels, great bone structure, and here Carter was with his eyes on Jenny, looking her over and seeming, dare Jenny think it, thirsty. Not really one for drawing attention to herself – at least not anymore – Jenny didn't mind admitting that she liked it when guys found her appealing. She didn't look her best, really. Old, faded jeans, an even older pair of ankle boots, a plain grey vest and a black blazer fresh from the dryer. It was still creased, but she was too busy to care when she'd thrown it on.

And yet Carter still had his eyes on her, and they were an attractive pair of eyes too.

Tabitha pulled on his arm and he came back to himself, clearing his throat and hailing down a cab. Jenny began trying to fix her phone once more, setting off down the street, but just as she passed him – and with Tabitha busy getting into the cab and giving the driver directions – Carter put his hand on her arm and handed her his business card. Jenny's eyes widened in shock and she looked up at him.

'Seriously? You're on a date.'

'Just the first one,' he said, slowly pulling his hand away. He grazed the inside of her wrist and lingered there for a moment, before biting his lip and turning into the cab. 'Hope to see you around, Jenny Humphrey.'

With that, the cab sped off and was lost in the sea of traffic. Jenny was still staring after it moments later, his business card in hand. Shameless, she thought, crinkling her nose again. Shameless… and somehow appealing? Jenny was barely twenty four. She liked having her fun, but given her history, she'd resolved to stay away from UES men. That said, if Carter was living in London he wasn't exactly an Upper East Side guy anymore.

That was six months ago, and now Jenny found herself staring at him, still groggy from sleep, as he stretched and ran his hands through his hair. When he caught her looking, he winked, and then stood up himself. He walked around the end of the bed and to where she was standing. He wrapped his arms around her bare waist and slid one hand down the back of her panties. Jenny's eyes fluttered and she sucked in a breath, gently pushing him away.

'I have a flight to catch,' she said quietly, struggling to get the words out as his hands roamed further and he started to kiss down her neck. One hand was on her chest now, drawing a line with his fingertip down and between her breasts.

'You could just stay,' he murmured, his hot breath now up by her ear. She reached down and grabbed his wrists to stop him.

'I have to go,' she said seriously, but she dissolved into giggles as he broke free and tickled her waist.

'Just stay one more day,' he said, pulling her back down to the bed, 'and one more night,' he went on, rolling them over so he was on top. He liked being on top.

Jenny wriggled out from underneath him and grabbed a towel from the airer. 'As fun as that would be,' she said, recalling their many, many passion fuelled nights, 'I have to get back to Manhattan. Dan's proposing to Serena and he wants me there for everything. Plus, Blair and I have to start thinking about the new line. It's getting more difficult to work from across the globe, and you know how I love staying at Casa de Bass. The sheets are divine.'

Truth be told, she'd been thinking of heading back to New York full time. She hadn't mentioned it yet, not that it would matter too much. They were just fuck buddies really, friends at a push.

'I thought you preferred my bed,' he quipped, licking his lips. At that, Jenny smirked. She went through to the bathroom and started running a bath. Carter came up and pressed his body against her back as he turned off the taps. He led her to the other side of the room.

'Don't you think a shower would be more fun?' he asked, and she couldn't disagree.


It was early evening when she landed at LaGuardia. Blair had sent a car and a change of clothes ahead for her, with a note that read:

Impromptu benefit at the house with some potential investors.

For as long as she could remember, Jenny had never known Blair to be impromptu about anything. Everything was meticulous, carefully planned, right down to what time the Queen B herself would make her entrance. Not one to say no to a drink with friends, though, Jenny soon talked herself into the spirit of things. She changed in the back of the car. Thankfully the windows were tinted and the driver had rolled up the screen between the front and back seats. By the time they arrived at Chuck and Blair's house, the evening seemed to be in full swing. Jenny's suitcases were taken upstairs by Dorota, who Jenny greeted with a kiss on the cheek.

'How are Leo and Anna?' she'd asked, and Dorota had beamed with pride.

'Very good Miss Jenny, thank you. Miss Blair is wanting to speak with you.'

Jenny waved her off and walked ahead through the house. Strangely enough, it had become something of a sanctuary for her over the past few years. She felt safe there, like she was truly home. She was stopped in the living room by Dan, who swept her up in a bear hug, and then by Serena who drew her in to an even tighter hug and kissed her on both cheeks.

'Jenny!' her future sister-in-law – and former step-sister – flashed her famous smile. 'How are you? How was your flight?'

'Good and good,' Jenny said, accepting the champagne Dan had retrieved for her. 'Thanks. Have you seen Blair?'

Serena was still grinning, though Dan was noticeably less enthused all of a sudden. Jenny looked between them and waited for an explanation, but it didn't come. Instead she was surprised to find Chuck had snuck up behind them. He touched her back and she turned to embrace him.

'Jennifer, I trust your journey was pleasant? You look stunning.'

He was the first to comment on the dress Blair had sent over. He must have known it was his wife's choice. The dress was long, black and flowing but the ends of the fabric dissolved into lace by the time it hit the floor. It had some thick straps that criss-crossed over her back, and a cleavage enhancing v-neckline.

'Thanks Chuck. Is Blair around? Apparently I'm in demand.'

'Yes you are.'

Jenny turned once again, worried she might have a spell of dizziness. She found Blair crossing the room, and soon was engulfed in yet another tight hug. Blair then took her by the arm and led her through to Chuck's study, where she closed the door on the party so that it was just the two of them.

'What's going on, Blair?' Jenny asked, crossing her arms. She knew the woman pretty well, and she recognized the glint in Blair's eyes. There was a scheme at hand.

'You'll be happy to know that I've acquired you a date for the wedding,' she said, looking pleased with herself.

'What?' Jenny blurted out. 'Dan hasn't even proposed yet!'

Had she missed it? Why wouldn't Dan have said something? And why did Serena look so happy if they weren't even engaged yet?'

'Relax, Little J. As far as they're concerned it's just a potential suitor, but I happen to have a good feeling about this one. I fully expect him to be your date to the upcoming Humphrey-Van der Woodsen nuptials.'

'So he hasn't proposed yet?'

'No. Keep up, Jenny,' Blair admonished.

'Right,' Jenny said, grip tightening on her clutch bag. Her – now in working order – phone was inside, as were the many phone logs and text messages she'd exchanged with Carter. Suddenly she felt guilty about her somewhat double-life, and most of all about him. But they weren't serious. On cue, her phone sounded in her bag to alert her to a new message.

'Aren't you going to get that?' Blair asked, circling Chuck's desk and smiling fondly at a picture of their son, Henry.

'No,' Jenny said, in what she thought was a convincing tone. Blair stopped and eyed her suspiciously.

As much as Jenny liked to think of herself as a strong young woman, and a gifted liar, something about Blair always left her feeling not quite up to par. She couldn't lie to Blair, and sadly this was the one time she really should have been able to. Blair narrowed her eyes and moved towards her.

In an effort to distract her as her phone sounded for the second time, and then a third, Jenny tried a little too emphatically to change the subject.

'So who's the guy?'

The door to the study opened just then.

'Blair? Chuck said you were looking for me.'

Jenny's breath hitched as Nate walked right back into her life. It had been years, and he still looked as impossibly handsome as ever. Whenever she was in the city she just so happened to miss him by a few hours; she was always dashing off to London or Italy or Paris whenever he'd stop by, and he was busy over in Los Angeles.

In the time Jenny spent staring at him, Blair had snatched the clutch bag from Jenny's unsuspecting hands and pulled out her phone.

'Nate,' Jenny breathed.

'Jenny,' he replied, a gorgeous grin spreading across his face. Jenny smiled, but the moment was short lived, as Blair's shrill, scolding tone rang out in disgust.

'Carter Baizen!'


A/N: Wasssssuuuup? Hope you liked that little intro there. I totally get it if you're maybe a little confused over the time frame and where Jenny actually lives. She's sort of between places and has been for a while because she travels so much as part of her job. Carter became a sort of security blanket in London, where as Casa de Bass became that for her in New York. I always imagined Jenny as being someone who couldn't settle in one place or another for too long because she never really knew who she was. Is that a bit too philosophical? Whatever.

As for the timeline, I imagine Jenny arrives back in NY for Dan's proposal, roughly around four months before he and Serena tie the knot. I don't imagine it was a long engagement at all!

Thanks for reading this chapter, and I hope you stick with the story for the rest. Much more to come!

Please leave some feedback? It's better than cake, and it helps me get better! x