A/N: Regrettably, there are some discrepancies in the time frame in which this story takes place. Currently, Jenny is 23, and the Gossip Girl Wiki (I'm a thorough fact checker, me!) states her birthday as being on April 2nd. Based on the ending of season 6, I always assumed that Dan and Serena married around September time, because I felt we were being introduced to a new wave of Constance kids as they headed off to school to start the year.

Being that this story takes places roughly four months before the nuptials, and with Jenny still 23, I've decided that her birthday is now in June. It isn't crucial to the plot and therefore really doesn't matter, but I just wanted to get that in there to put to rest any confusion. If there even was any. If you didn't notice, or simply don't care, then let's just leave it there.

Moving on!

In this chapter, we delve a little bit further into Jenny's past, and touch very briefly on how she and Blair came together to create J for Waldorf. Despite their growing friendship being the primary one in Jenny's life as she readjusted, I always felt that in order to come back to the Upper East Side, Jenny had a lot of bridges to mend. Not least of all with Serena, which is what the flashback centres on. Let's be honest, Jenny made things preeetty difficult for our favourite golden girl in seasons 3 and 4. She owed S an apology.

But that's enough from me for now. Enjoy!

Sage Advice

'B, we really should just stay out of it.'

'Nonsense. The very well-being of our friend is at stake here.'

'I think that's being a little dramatic.'

Serena had more important things to worry about that day, and while she cared about Jenny just as much Blair - if not more – she knew that Jenny was perfectly capable of taking care of herself. And honestly she just didn't believe Jenny would be silly enough to date Carter Baizen. The stories about him from strangers were enough to turn anyone away, let alone stories from close friends and family. She'd grown to think of Jenny as a sister. They'd been sisters before, obviously, but not by choice. Now that Serena planned to spend her life with Dan, Jenny came as part of the package.

It was a package that Serena loved and trusted dearly.

Still, the persuasive tones of her best friend were difficult to resist. Blair Waldorf Bass was a well-oiled, perfectly manicured little machine. Serena huffed into the mouthpiece of her cell, tapping her foot.

'I'm actually meeting Jenny in a couple of minutes.'

'Wonderful,' Blair cooed on the other end. 'Now, I need details. How long, how often –'

'How often?!' Serena screeched, outraged.

She caught the eye of a middle-aged man sitting a few tables over and offered a smile in an attempt to recover some of her dignity. He promptly cleared his throat and fluffed out his paper, as if he hadn't even noticed her there.

'Really, S? You're going to play coy? We need to get to the bottom of this thing between Jenny and Carter, and snuff out the torch before his ship makes port again.'

'Oh my God,' Serena groaned, covering her face with her hand and leaning her elbow on the table. 'Blair, that's enough. She said they're just friends.' The door chimed and Serena looked up. Jenny waved and began making her way over. 'She's here, I have to go.'

'Find out!'

'Alright mom, I love you. Bye! Jenny, hey.'

Serena stood up and kissed her on both cheeks. She caught a breeze from the door as it swung shut and was thankful for it. It was turning out to be one of the hottest days of the year so far, and being only June, Serena was excited for what the summer would bring. Partly, anyway. She was also terrified of making it to the end of the month for a couple of reasons. The first was Dan. He was acting strangely, and had been for weeks now. He seemed nervous around her and dodged questions like where they would spend Christmas, and what Jenny might like for her birthday. It was almost as if he wasn't planning on being around. Serena knew she was probably, most likely, almost definitely over thinking things, but it wouldn't help to get a second opinion. That was where Jenny came in.

Few people knew Dan Humphrey as well as Serena did. Jenny was one of them.

The second reason she was dreading and wilfully expecting the end of the month in equal measure was this:

Serena was late.

'How's Lily?' Jenny asked, sitting down. She picked up two menus and handed one to Serena.

'My mom… is great, thanks. She and Dad are enjoying Bali at the moment.'

'I'm surprised they get cell reception over there. Weren't they staying off the grid?'

Serena smiled and bit her bottom lip. 'Right. Yeah. Lucky five minutes I guess.'

Jenny was looking at her suspiciously. Serena's ability to bend the truth used to be pretty good, given who she was best friends with, but Jenny had been fierce in that respect too, and being queen of Constance had taught her a few things. Serena knew right away that Jenny could see straight through her, but she soldiered on so as not to disappoint Queen B.

'How are things? Are you excited for your birthday?'

Jenny smiled broadly. 'I am. Things are going well right now. I'm finally inspired for the new line – Blair and I bounced some ideas around this morning and we're even thinking of dabbling in menswear. High end couture suits, that kind of thing. She also mentioned a promotion which is really exciting. I think I'd like to be back in Manhattan,' Jenny paused briefly. 'As long as I could keep my feet on the ground and my seventeen year-old self at bay…'

Serena was nodding along as Jenny spoke, taking in her words but not really listening. She was bursting with questions and panic and worry and just couldn't hold it in any more.

'Is Dan going to break up with me?' she wailed, staring at Jenny across the top of their menus.

Jenny's eyebrows went up in surprise, and Serena couldn't blame her.

'Are you kidding?' Jenny asked, completely serious, as she set down her menu. 'Serena, no of course not! Why would you even think that?'

'He's been distant lately, acting weird. Every time I bring up anything to do with the future, from your birthday to this Christmas and next year, he gets all wordy and nervous and finds a way to change the subject, or drops the conversation.'

Serena could hear herself getting clingy, but she just didn't care. When it came to Dan Humphrey, she was as clingy as she cared to be, and as loving and loyal and lovely as she could be. Jenny's expression had changed from surprise to something else. She was trying not to look Serena in the eye. The guy with the paper a few tables away was not that interesting.

'Spill,' Serena said, eyes narrowing.

'There's nothing to spill,' Jenny insisted, slapping on one of her most eager smiles to date. She grabbed at her menu again. 'I might get eggs. Do you want eggs?'

'Jenny.'

'But then I am a Humphrey, and the waffles here are so good.'

'Jenny.'

'Dad would flip if he thought I was eating anyone's waffles but his own-'

'Jenny!' Serena had hissed and stolen the menu away. 'Tell me.'

Jenny was resolute and refusing to budge, so Serena had to invest in her Blair tactics. She pursed her lips and leaned in, quirking one eyebrow just enough to make Jenny sweat under her gaze.

'Fine. If we won't talk about Dan, let's talk about Carter Baizen.'

Jenny's otherwise engaged gaze froze on Serena and she visibly stiffened, before dissolving into a guilty little sister.

'I can't tell you what he's planning!'

'He's planning something?'

Jenny realized her mistake. 'No…'

'What's he planning?'

'Nothing!'

Serena grinned and sat back, triumphant. 'He is planning something. Is it a weekend getaway? A vacation in Europe?'

'I'm not saying anything else.'

Serena clapped to herself, still smiling, and then reached for Jenny's hand across the table. She'd been so worried this morning and now her mind was half at rest. With the issue of Dan out of the way, she could focus her energies more on the issue of her late period. It was probably just the stress of worrying about her relationship, and she'd get it soon enough. She felt Jenny squeeze her hand, and saw the look in the youngest Humphrey's eyes. She'd seen it before, a few times. Once at Serena's mother and Rufus' wedding, when they'd said their vows, at the guerrilla fashion show when she'd seen how much people loved her designs and she'd run into Nate's arms, and then again when she'd returned to Manhattan in the Spring of 2015, two years earlier.

Jenny looked so happy, Serena mused, as butterflies flew in her own stomach. Good things were coming, she could tell. She'd forgotten entirely about the Carter Baizen situation.

'Just take my advice,' Blair chided her.

Jenny rolled her eyes on the other end of the phone and somehow, she thought, Blair probably knew and it only added to her irritated tone.

'I don't know if this is a good idea.'

'Of course it is,' Blair said sharply. 'Jenny, we've been through this. Waldorf Designs would like to bring you aboard, but we won't be welcoming you back to Manhattan while there are so many unresolved issues between you and my circle.'

'Right,' Jenny conceded. 'Okay. I'll call you when I land in Paris. Can you email the itinerary, please?'

'Already sent, mon ami. Now get to it. Au revoir!'

Blair clicked off just as Henry began sobbing in the background. Jenny heard enough to know Henry wanted his Daddy.

Considering Serena Van der Woodsen was one of the nicest people on the Upper East Side, at least that Jenny had met, she'd never been so nervous to talk to her. As she rode the elevator up to Serena and Dan's apartment in her old building, Jenny wondered which of Serena's famed personas would meet her when she arrived. It could be her loveliest one, wherein she loved everything and everyone, or it could have been the brief, head-bitch-in-charge one she'd adopted briefly at Constance during her war with Blair. Jenny hoped it was the former, and given Serena's unearthly capacity for forgiveness, she didn't think it was too much of a stretch to hope for it.

They'd seen each other in the few years since Jenny had left Manhattan for good, at Christmases and birthdays, but they'd never spoken a great deal and, honestly, Jenny didn't blame her. It wasn't just that she'd sabotaged Serena's relationship with Nate; that was child's play and in the past, and Serena was in love with Dan. The real, lingering issue between them was what had happened during Juliet's run of terror.

She'd convinced Jenny to help in her plan to take down Serena, and it had escalated so quickly that Jenny became caught up in consequences she hadn't intended on. Jenny had gone straight to Blair to set things right, which she knew did little in terms of gaining Blair's forgiveness for the Chuck incident. But it had set Jenny on the path of redemption she'd so clearly needed.

She was at their door before she'd had a chance to look up and, knocking thrice, she stepped back and waited. Dan was at a signing, which oddly Jenny preferred. It would be better for her and Serena to do this alone. The door opened then, and as the sunlight hit her hair, Serena stepped forward in a mane of gold. Glorious as ever, Jenny thought. Unlike her teen years, there wasn't a hint of resentment in her mind. Serena smiled. It was small, but it was there.

'Hi Jenny.'

'Hi.'

They spoke at length, for what seemed like hours, and drank tea and ate some cake Serena had made. She claimed she was nesting, and Jenny had laughed. Being in Serena's company had never been this easy before, not even in Jenny's freshman year at school. Back then Serena was terrifying, in a good way, and it took a while for Jenny to grow into herself. When she did things went a little downhill, but that was neither here nor there. Serena asked about her designs, and she asked about Serena' charity work. She was the head of several committees at just twenty five years old – a far cry from her cotillion introduction. Serena was still consulting on films here and there, and she'd become a great reader of Dan's work, offering notes and suggestions.

Jenny envied the way Serena and her brother just seemed to fit. Anything else didn't work. That was something her teenage self would agree with, but for all the wrong reasons.

'Serena,' Jenny said a little later, when they'd settled into the more serious side of things. 'I'm so sorry. For everything with Juliet. I never wanted any of that to happen. I was an angry, selfish kid.'

'I know you're the one who told Blair what happened,' Serena said, setting her tea aside.

'Doesn't make up for it,' Jenny said, dismissing Serena's understanding. She didn't deserve it. 'And I'm sorry about Nate. Trying to sabotage the two of you. I was so stupid.'

'You loved him,' Serena said, like it was fact. Jenny couldn't argue.

'I think I loved the idea of him back then-'

'No.' Serena reached over and squeezed her hand. 'You did. First loves never really go away, either. They mark you. They keep in your memory and your heart.'

'Doesn't matter anyway,' Jenny said, half-laughing at herself. 'Nate never saw me as a viable option.'

'Given the way he looked at you after your fashion show at my Mom's event, I don't think that's true.'

There was a pause as Jenny thought back to that night. If she could go back and relive any one day of her life over and over, it would be that one. She'd finally shown people what she could do, what talent she had. Agnes wasn't a crazy bitch yet – she was a genuine friend, and Nate… Nate wanted her. She could feel it in the way he'd kissed her. That was something she did relive sometimes.

'Jenny, do you still care about him?'

Jenny shrugged. She could feel tears pricking on her lash line but blinked them away. 'I think I always will, but that's all in the past and it's better left there I think.'

Serena leaned over and drew Jenny into her. 'If you'd seen the kind of things I got up to not that long ago over Dan and Blair, you wouldn't feel the need to apologize. But thank you.'

They let go and Jenny held up a plate of chocolate cake. 'All is forgiven?'

Serena giggled her famous giggle. 'All is forgiven.'

They ate and drank more until Jenny had to head to the airport to catch her flight to Paris. On her way out the door, Serena gave her another hug.

'You know, Jenny, just because you think something's better left in the past, doesn't mean it is. Look at Dan and me. He fell in love with Blair, but ultimately he and I were meant to be. I think sometimes people need to be apart, so they can realize they need to be together.'

She squeezed Jenny's hand and said a final goodbye. On her way to the airport, Jenny couldn't help but feel calm. She was repairing her relationships and everything she'd damaged in her wake when she'd declared war on the Upper East Side, and it felt good. Having Serena back in her life was surely going to be a blessing, and working with Blair was making her happier than she'd been in a long time. Things were looking up.

There were others she'd inevitably have to face, but they were for another day. For now, she was going to enjoy Paris and, perhaps, wonder at Serena's words.

Nate was feeling hounded. In between meetings, he'd managed to steal away a break in his office at the Spectator. Head in his hands, he sighed heavily and closed his eyes. There was a lot of talk surrounding him lately. Not about whom he was dating, if he was dating, if he was even straight or anything else to do with his – currently failing – love life. It was all to do with a tip that had been leaked to the Post. Apparently Nate was planning on running for mayor. This was all news to him, of course. His grandfather had made the call to him some days earlier, overjoyed at the news and demanding to know why he hadn't been included on the matter.

Nate had been quick to dash his hopes, but still the journalists called for quotes and asked for interviews. His assistant, Katie, just so happened to be going away on maternity leave too, and that only added extra strain. She was superb at handling these kinds of things. He was going to miss her. But she had more important things to attend to, obviously. Speaking of, he still had to get through the pile of applications to cover the position while Katie was away, and he hadn't even looked at them yet.

Just as he turned his attention to them, he heard Katie talking with someone in the hallway.

'Do you have an appointment?' Katie asked.

'No, but don't worry. We're old friends!'

He checked his watch. Was he late to meet Jenny? Had she tracked him down? His stomach gave an involuntary leap at the thought. He stood up and straightened his tie, and just as the door started to open he cracked a grin. But it wasn't Jenny who met him at the threshold. Instead of leaping again, his stomach plummeted.

Sage Spence was, most certainly, not Jenny Humphrey.

'I'm sorry, Nate,' said Katie, glaring daggers at the back of Sage's head. 'She just barged right past me. I can't exactly fight her off.'

Nate shook his head. 'It's no problem, Katie. Why don't you take a break? Put your feet up.'

She looked grateful. 'Thanks, Nate.'

He closed the door on her as she walked away and then turned back to Sage. She was sitting on his desk; impossibly tanned legs crossed in front of him, on full display thanks to her – inappropriately short – black skirt. She was biting her lip and smirking as he came closer, but Nate wasn't exactly in the same frame of mind.

'You can't just barge into my office, Sage,' he said with authority, though his hands in his pockets gave off a distinctly casual vibe. She didn't seem to mind either way though. She turned to her satchel and pulled out a thin file.

'My résumé,' she said, handing it over. 'For the assistant position.'

Nate eyed her, eyes slightly creased, and tried to figure out if she was making fun of him. The last time they'd seen each other had not been very pleasant. It was his twenty third birthday, and they'd really been on the rocks for a while. She was busy choosing colleges and wanted to stay local so they could go on as they were, but Nate felt the relationship was coming to a natural end and, honestly, he was looking for something more mature. It surprised even him, and when he brought up the fact that there was a significant age difference, she went on and on about how it hadn't seemed to bother him when they were in bed together. Tantrums were thrown – on both ends, he might add. Nate could still carry a mood with the best of them. She'd called him unprofessional, and a terrible worker.

Yet here she was, fresh out of Columbia J School and sitting on his desk, much like she would in the long-ago evenings as a surprise. Except she was wearing significantly more clothes this time around.

Nate looked up at her from the paper in his hands, impressed.

'Journalism and business? Not what I expected.'

'Well I'm just full of surprises.'

Sage was more relaxed now, legs uncrossed and slightly open. Nate tried hard to keep his eyes on her face, but she was making it very difficult. One hand slid down her neck, the other rested on her thigh. She clearly remembered just how much he liked a woman's neck, or more specifically the spot just between the neck and the collarbone. He swallowed. He was a professional, dammit, and she was being everything but. He moved around the desk and she jumped down to follow him. He sat in his chair.

'What's wrong?' she asked innocently, leaning over his computer.

'Sage, I don't know if you being my assistant is such a good idea.'

She pouted, and he wondered for a moment if she'd done any growing up in their four years apart. Really, she should have. He had potential investors sitting just a room away, waiting on the Editor in Chief himself to come through and explain to them why working with the Spectator was the best thing they'd ever do. He reminded himself to mention the jet again. Since expanding coast to coast, it just made things easier. Chuck had gifted it to him originally, but he'd paid his best friend back in full. Nate realized how hard he was concentrating on anything but Sage, who had come around to his side of the desk and now stood in front of him.

'I actually think it would do us both the world of good,' she explained, hands on the arms of his chair and leaning down.

She came eye level with him, and Nate stood up and out of her reach once again.

'Sage, this is ridiculous,' he said, laughing. 'I'd be your boss. We have a complicated enough past as it is – I don't think you working for me, and then working it for me is a good idea. I'm sorry, the answer's no.'

She seemed disappointed for a moment, but soon perked up and gave him another smile.

'Well then, I guess this is okay.'

She closed the distance between them quickly, and Nate was so distracted by her rounding on him that he failed to notice Katie's voice in the hall once again.

'Go ahead, it's a free for all today.'

'Thanks!'

Sage kissed him full on the mouth, and he was taken back right away to when he was twenty two and they were spending late nights at the office, in every room, on every possible surface. He dropped her résumé on the floor just as the door opened and someone exclaimed:

'Oh, I'm sorry!'

Dazed by the sheer force of Sage's kiss, it took Nate a moment to focus on Jenny as she stood in the doorway, mouth agape and eyes wide with shock.

'I was just coming to say that I can't make lunch.'

She slammed the door just as quickly as she'd opened it and just in time too, as the investors had just started filing out of the conference room.

Sage is back! Didn't she say Little J used to be her idol once upon a time? I'm not sure it'll go down that way…

Please leave some feedback – it's much appreciated. Shout out to Dr. Holland, whose work I adore, and who leaves such lovely reviews! xoxo