Reckless Hearts // a "Gossip Girl" Next Generation Story

“Hey... You probably won't even listen to this, but I- I don't know... I guess I just wanna apologize. For showing up at your place like this. For trying to make you talk even though you said you weren't ready. But the thing is, Annie, I am ready to talk about this. I have been ready to talk about this for over a month now. And I know you feel guilty, Annie. I'm feeling guilty, too. But we can't just ignore what happened. Annie, we slept together and all the silence in the world isn't going to undo that...”


1. pt.1




Hello, Upper East Siders,

did you miss me?

I know, it's been a long, quiet summer, but things are about to get exciting. Dust off those party dresses, because it looks like our Queen and her favorite Lady have finally pulled up stakes in St. Barts and are on their way to spice up life in the Hamptons just in time for Jack Bass's annual Fourth of July party.

We're all left to guess what this means for our very own Royal Couple. Prince Charming seemed unusually reclusive these past few weeks – is this thunder I hear rolling up on Royal Cloud Nine or are we in for a reunion worthy of a fairy tale?

And what about fair Lady Anne?

Rumor has it she's been rejecting an awful lot of calls on her Caribbean getaway. Does this mean there's finally a suitor somewhere waiting for her to answer his desperate courtship?

I think it's about damn time! After all, she can't play the Royal Third Wheel forever. It's safe to assume that Queen C has no intention of sharing her prom date for yet another year. Not when this time there's The Crown at stake.

It's the Fourth of July, bitches. And this girl right here's expecting some fireworks.

This hot summer just got even hotter.

-XOXO- Gossip Girl






“I hate this fucking hellsite!”, Celeste Kingston growled and dropped her phone back into her purse with an exasperated huff. “What a load of crap.”

“And yet you can't quit it”, her best friend Annie Montgomery gave back with a light chuckle. “You love it when they talk about you. Especially when they make up drama.”

She leaned back in her seat and looked out at the East Hamptons passing by the town car's tinted windows.

Being able to come here whenever she wanted had always been one of the few things she had unreservedly loved about moving to New York, but this time the picturesque houses and glittering coastline didn't have the same calming effect on her they usually had.

She was practically buzzing with anxiety – a strange, tingling sensation like ants crawling right under her skin, which grew worse with every passing minute. She had known that this moment would come eventually, that she couldn't run away forever, but now that they were almost there the thought alone was enough to make her feel nauseous.

“All publicity is good publicity”, Celeste stated. “Ever since the golden days of Blair Waldorf and Serena van der Woodsen no one has been proclaimed Queen of anything if Gossip Girl didn't find them worthy of... well, gossip. Speaking of which...”

She had been checking her reflection in a small hand mirror, fixing already flawless ginger beach waves – strawberry blonde, her hair colorist Hugh called it, heavy on the strawberry - but now she turned to Annie with a conspiratorial grin. “You know that you're gonna have to tell me who's been calling you all summer eventually, because that's what BFFs do. You might as well just get it over with and tell me right now.”

“I already told you it's nothing”, Annie replied weakly, not daring to look her best friend in the eyes as she lied to her again. She had repeated that same lie over and over for weeks now, but it still left a stale taste in her mouth. “Just some guy I met before we left. Turns out he was far more interested than I was, so I stopped answering his texts. I'm sure he'll stop calling eventually.”

“Next time he calls just give me the phone”, Celeste suggested with a shrug. “I'm sure I'd get the message across loud and clear.”

“I really don't think that's necessary”, Annie replied quickly. Maybe a little too quick, but thankfully Celeste could hardly go two minutes without getting distracted by her phone, so she was already too busy scrolling through her messages to notice.

“Right, whatever... Keep your stalker. Anyways, Maddie's still in Europe, but The twins are gonna meet us at Jack Bass's garden party”, she said in that tone that her boyfriend Quinn Davenport called her “that's an order, not a suggestion” voice, so Annie didn't even bother trying to tell her that all she wanted from this day was a long, hot shower and to hide away on her porch with a good book until it was time to go to bed. She would have been fine to spend the rest of the summer like that. But the Queen had spoken. Garden party it was.

Annie breathed a silent sigh of relief when they pulled up in front of her grandma's beach house. It was the Fourth of July so naturally traffic from the airport had been an absolute nightmare and Annie couldn't wait to finally get out of that car. In fact, she was so eager to get out that she didn't even wait for the driver to come open the door for her.

“Thank you so much for this, trip, Cee”, she really hoped that she managed to sound at least somewhat genuine. Taking her to the Caribbean for a month had been a very generous gift after all – even if the only reason Annie had come was that she hadn't been able to come up with a good enough excuse not to. And now she was glad it was over.

The past four weeks had been overall terrible for the both of them – and for each of them for very different reasons – but ever since they had gotten on Celeste's father's private jet about seven hours ago, Annie had been feeling downright claustrophobic. Like all the lies were weighing her down, making it harder and harder to breathe.

She was damn lucky that Celeste had her own problems to chew over. Otherwise she probably would have wondered what the hell had turned her low-maintenance best friend into such a train wreck all of a sudden.

“You should call Quinn when you get home”, she said as she took the bag and suitcase the driver handed her from the trunk, trying not to trip over the way it felt to even say his name. “Tell him before the story hits the tabloids, so he can be there for you when it does.”

“There is nothing to tell”, Celeste hissed, her mouth a tight, grim line. “This... thing will die before either of us can say 'National Enquirer'. And this is the last time you and I are ever gonna speak of this, do you understand me?”

Normally Annie didn't take well to Celeste talking to her like she was one of her Constance Billard underlings, but right now all she wanted was to go inside and finally be alone, so she decided to let that one go.

“Got it”, she said softly. “I didn't mean to upset you, Cee, I'm sorry. ”

“And I'm sorry I snapped at you.”

And as if it wasn't 'once in a blue moon' enough to hear Celeste apologize for anything, she then further surprised Annie by slipping out of the car and engulfing her in a tight hug.

"Thank you for being there for me", she whispered, her voice cracking ever so slightly. "I would've gone crazy without you..."

"Cee..." Annie had to blink back tears. There was so much she wanted to tell Celeste in this moment. How much she loved her. What their friendship meant to her. How badly she had fucked up... But she couldn't.

Because she didn't want to lose her. Because what she had done was unforgivable. Because saying the words out loud made it real.

She felt like this day's anxiety was very rapidly turning into a full fledged panic attack.

"I should get going", she said and took a step back. "I really need to wash off the travel smell and figure out what to wear tonight."

“Girl, same”, Celeste gave back with a shaky laugh and slid back into the backseat with enviable elegance. “Do you want us to come pick you up?”

“No, thanks.” Annie shook her head. The prospect of spending any amount of time in a confined space alone with both Celeste and Quinn was probably in the top five of things which for the past few weeks had kept her awake at night. “The Bass's house is just down the street. I think I'm gonna do something for my carbon footprint and walk.”

“Fine by me.” Celeste shrugged and motioned for the driver to close the door. “See you there then.”

Annie felt like a weight was being lifted off her shoulders when the black car was finally rolling down the driveway, but just when she was about to turn around and go inside, the rear window opened and Celeste's grinning face appeared.

“Just so you know, Gossip Girl's right!”, she called. “I'm not gonna share my prom date with you again. Put on something hot tonight, we're gonna find you a boyfriend!”

Luckily the car was already so far away that Celeste didn't see how her best friend blanched at her cheery little jab. Annie waved one last time and then the car was gone. She unlocked the front door, completely forgetting about her bags in her eagerness to get inside and then she was finally, finally alone.




Annie quickly closed the door behind her, pressing her trembling hands flat against the cool, painted wood.

The house was completely silent save for the distant roll of wave outside, the ticking of the antique mahogany clock in the living room and her own ragged breathing.

She closed her eyes, trying to focus on the soothing sound of water lapping on sand and on her own breathing - in through the nose, tick tock, hold, tick tock, out through the mouth, tick tock - until she felt like she was no longer about to hyperventilate. She was still feeling miserable, but at least she wasn't in full on panic mode anymore.

Yes, she had gotten herself in an awful fucking mess, but she needed to keep a clear head if she wanted to find a way back out of it that didn't involve wrecking her own life and those of the people she cared about the most in the process.

"A little late for that", a nasty little voice in her head taunted. And it was right.

There had been plenty of moments when she could have stopped all this from happening - last month or back at prom and even a little bit on every single day of the past two years. But she hadn't. The damage was done and now that they'd spend the rest of the summer in the Hamptons together, it was only a matter of time before the truth would come out and leave her with nothing.

She had half a mind to just board the next bus into the city, spend the rest of the summer hiding in the Manhattan penthouse or maybe go and visit her grandparents in LA. It didn't even matter where she went as long as she didn't have to be there. With her bags still conveniently packed on the porch outside it was a tempting idea. Very tempting.

But Annie knew that if she ran now, she would just be buying time. In September she would have to return to school and Constance Billard was a cesspool for gossip. After all it was the birthplace of Gossip Girl and very possibly the lair of 'Her' current incarnation.

There was no way her secret would stay hidden there. Shit would hit the fan eventually, only then she would have to deal with the fallout in front of all her classmates. Even a decade later there was still talk at Constance about the infamous 'Blair Waldorf Pregnancy Scare of 2008' and Nate Archibald decking Chuck Bass in the face in front of the school. Annie could live without any such public scene.

So running, while tempting, wasn't an option. Plus, her grandma's beach house was probably her favorite place in the world, where else was she gonna feel save enough to get this whole mess sorted?

“Grow a pair, Montgomery”, she muttered to herself.

She opened the front door to pick her bags from the porch before her cowardly lion side reared its ugly head again and made her change her mind. Her grandma was spending the summer in Florida and her dad had gone back to the city two days ago for an urgent client meeting and wouldn't be back for at least a week, so for now she had the place to herself. That gave her plenty of time and room to figure things out in peace. If only she didn't have to go to this stupid party...

As if on cue, her phone buzzed softly in the back pocket of her jeans. She sighed. Probably Celeste with some party 'emergency'. Annie took her phone out and looked at the screen. It felt like suddenly someone had knocked all air from her lungs. It was a message from Quinn.


Quinn Davenport (2:25pm): We need to talk.


Well, fuck.

She hastily put the phone back, as if this way she could just unsee the message. She had ignored Quinn's calls and texts for weeks, what difference did another day make? She wasn't ready to face him yet - would probably never really be ready again – but it seemed now that Gossip Girl had told the whole world she was back, he wasn't gonna let her ghost him like she had done for the past month.

Her phone buzzed again. And again. In the end Annie put her it in her bag which she left in the hallway. With Quinn just a quick walk along the beach away, instead of a five-hour flight she didn't trust herself not to cave if he messaged again or even worse, called her.

All she wanted to do now was unpack, maybe eat something and spend the next eight hours bracing herself for what was to come.
Her grandma had spent the last two years and an obscene amount of money on the house getting both refurbish and modernized, so while the outside was still all rustic Hamptons charm, the inside was dominated by wide open spaces, white walls and beige upholstery.

When Annie entered the polished, open kitchen there was a freshly filled fruit bowl sitting on the counter. Upon a quick inspection she found that the kitchen cabinets too were well-stocked with the essentials. There was even milk and yogurt in the fridge. When she picked an apple from the bowl she found a note on the counter. She immediately recognized her father's handwriting.


I had Katherine restock the kitchen for you. See you on the 13th. Love, Dad.

PS: Your grandma can smell the remains of a party through three layers of bleach, so don't do anything I wouldn't do.”


Annie smiled at the note. It was so like her dad to tell their housekeeper to prepare the house for her, even after she had told him he didn't need to. Sometimes she thought that for Declan Montgomery she would always be a twelve-year-old with braces who couldn't possibly take care of herself for a week. It was endearing. Annie had really missed him while she was away. She would definitely call him later.

She took her stuff and went to the living room. There she opened the massive glass sliding door which led into the back garden with access to the beach and stepped out onto the terrace.

The Garden was her grandmother's pride and joy – beautiful, old trees, meticulously trimmed hedges and rosebushes of all sizes and colors that filled the air with almost dizzying fragrance. The spacious lawn had seen a lot of rousing garden parties in its time.

Annie closed the glass door behind her. As much as she loved the house, she had no intention to be staying there, because her favorite spot was the little pool house at the far end of the garden. Even if in that case the 'little' house came with a separate bedroom, its very own kitchenette and a bathroom with a rain forest shower. Annie loved being able to take a quick dip in the pool without having to walk through the whole house and garden to get there. She loved using the outside shower on a hot day and she loved that the pool house was right next to the garden gate that led to her family's small strip of private beach – not that anyone in her family actually cared much about who used it so long as it was clean when they left.

It was a secret no one really tried to keep that sometimes – when her dad and grandmother weren't there, of course – the resident kids would have their beach parties on the Montgomery's property, as it was a lot nicer than most of the public beaches. And they always cleaned up before they left, because the last thing they wanted was to come back and find a brand new fence around their favorite hangout.

The key to the pool house was hidden under a fake stone by the door – not very creative, but with a high end security system there wasn't much need for creativity there. Annie unlocked the door and carried her stuff inside. She dropped her bags in the bedroom, then went and opened all windows to let the fresh smell of sea breeze in. The tidy side of her thought she should probably unpack, but the restless, anxiety ridden main part of her just wanted to get in the pool and do laps until her body screamed and her mind went blank.

So she did just that. She slipped into her favorite pastel striped Farrah swimsuit, grabbed a towel from the bathroom and went outside. She quickly showered – the past eight hours weren't something she was keen on carrying into the water with her – then took the steps by the narrow end to get into the pool.

When the pool and pool house had gotten their big make-over last year, the pool had been tiled in a very expensive, very intricate mosaic that shimmered in various shades of green, blue and purple and as Annie glided through the water as fast as she could, it felt like she was surrounded by countless glistening mermaid fins. It was a mesmerizing illusion and soon Annie was so lost in the fantasy it conjured that at least for one moment she was able to put her worries on mute. She didn't stop until her lungs were burning and her arms felt like lead. The last thing she expected when she came up, gasping for air was to find Quinn Davenport standing at the pool edge, watching her.

“That was impressive”, he said with that stupid soft smile that had never failed to make her weak in the knees ever since she had first met him right there in the Hamptons five summers ago. And even now, despite everything that had happened, the mere sight of him and that stupid smile was enough to make her stupid heart skip a beat. “Are you planning on trying out for the swim team this year?”

He could've fooled her with that smile and the light tone to his voice, but she knew him too well. His eyes gave him away. Always his eyes. To Annie, Quinn was the worst liar in the world and it was all in his eyes. She asked herself if Celeste knew that, too.

“What are you doing here?”, she asked, her tone sharper than she had intended to, as she hastily scrambled out of the water and grabbed her towel from a sunbed. She quickly covered herself with it, even though she knew it was silly. Nothing there he hasn't seen before, idiot.

But she wasn't going to be doing... this standing there in nothing but a dripping wet swimsuit while he looked like a walking billboard with his blue chino shorts and light gray polo shirt. His hair was a charmingly windswept mess and the sun had turned his usually caramel brown waves an almost honey blonde shade. He had the natural tan of someone who spent all day every day at the beach and even from where she was standing, Annie could see the freckles on his face and arms.

“Well, I figured it'd be much harder for you to pretend like I don't exist if I came here instead of sending you another text”, he gave back dryly. Annie felt like she probably deserved that one. “I knocked at the front door, but when no one answered I figured you were probably out here or in the pool house and I still have the code for the garden gate so...”

He trailed off and took a few tentative steps towards her, but stopped, when he saw her moving back ever so slightly. He looked at her, brows furrowed. There was no mistaking the fact that he was hurt. Annie opened her mouth to say something, then closed it again. She sighed. What a fucking mess.

“You cut your hair”, he said, breaking the uncomfortable silence between them. “I like it.”

“I felt like a change”, she mumbled, one hand unconsciously reaching for a strand of wet, chin-length hair. It had been a spur-of-the-moment thing, back in St. Barts when she had felt like crawling out of her own skin. Celeste had dragged her to her favorite spa on their third day there. It had been the usual – mani-pedis, facials and massages, but while Celeste had finished her day by getting a professional blow-out, Annie had ended up getting almost ten inches of hair chopped off.

You know”, Celeste had quipped while inspecting her best friend's brand new feathered bob. “If I didn't know better, I'd say someone's getting over a bad break-up.” Of course Annie had laughed it off, but her stomach had churned with guilt.

“You shouldn't have come here”, Annie said, the thought of Celeste enough for her to stop beating around the bush. She needed to end this before Quinn had a chance to say what he had come to say. He was looking at her in that way again. The way that made her heart flutter, the one that made his hazel eyes crinkle softly at the corners. She remembered the times she had caught herself wishing he'd be looking at her like that, but now all it did was fuel the feeling of guilt she had been carrying around with her over the past weeks. “I know you think we need to talk about... about what happened. But we don't.”

“Of course we do.” For a moment it looked like Quinn was going to step towards her again, but he didn't. Annie knew that it was probably because of how she had recoiled from him earlier and she couldn't fight the pang of regret. She had never met anyone who was so aware of the way their physical appearance affected others.

Standing at 6'3 with the broad shoulders of a competitive swimmer, Quinn knew he was intimidating to people who didn't know that somewhere deep down he still felt like the lanky thirteen-year-old boy whose limbs never really seemed to fit in with the rest of his body.

The last thing Annie wanted was for him to think that she could ever feel threatened by him. But she couldn't tell him that the thing that actually frightened her was the way she was feeling whenever he was close to her.

“Please, Annie”, he begged softly. “We can't just pretend like nothing happened.”

“I can't do this right now”, she shook her head. All she wanted was for him to leave, so this fog around her brain would lift and allow her to think clearly again. She almost laughed at her own stupidity. Apparently now she was also lying to herself. She hadn't been thinking clearly in four weeks, three days and fifteen hours. But Quinn had completely blindsided her by turning up at the house like that and now she felt cornered. Trapped. This was not at all going the way she had pictured it – the very few times she had actually allowed herself to even think that far. “I need more time...”

More time? Annie, you've been gone for over a month. You didn't take any of my calls or answer any of my texts. How much more time could you possibly need?” There was an urgency in his eyes – a passion – that made Annie's inside hurt with longing. If only the circumstances were different, maybe they could – “Cee's called me two times already. She wants to see me. We need to talk about what we're gonna tell her.”

Cee. The sound of her best friend's nickname brought reality crashing back in with a bang and the old panic right along with it.

“There's nothing to tell”, she croaked. “She's probably waiting for you to call her back. You should leave.”

“Annie...”, he pleaded. He moved, raising his hand as if he wanted to touch her and for a brief moment every last piece of her begged her to just let him. But she couldn't do that. It wouldn't have been fair to him. To herself. To Celeste.

“I told you to leave!”, she cried, her voice breaking on something close to a sob. “Please, Quinn!”

Annie didn't know what ultimately did it – was it the tears brimming in her eyes or was it the fact that she was practically radiating despair at this point? - but it was like whatever hope or confidence this whole confrontation had left him with had just been drained from his body. He looked younger suddenly, and just as vulnerable and hurt as she was.

“Okay”, Quinn said bleakly. “I’ll see you at the party.”

Then he turned around and left, his whole posture a picture of defeat. He didn't look back at her once. And Annie found herself frozen in place, still staring at the garden gate long after it had fallen close behind him.

She faintly noticed that she was shaking so hard her teeth rattled and realized she was still standing there in nothing but a wet swimsuit. She quickly went inside, stripping down and stepping inside the shower. She stayed there until the hot water ran out, then toweled herself off, slid into a soft, off-white dressing gown and went into the bedroom to unpack. All of this she did in a kind of misty haze where she was replaying the past minutes in her head over and over again until she wasn't even sure anymore if it had actually happened the way she remembered it or not.

When Annie was done the dated alarm clock on the nightstand told her that she still had at least four hours left before she had to get ready for the party. And even though she wasn't too keen on going – for obvious reasons – she felt like she was going to go crazy sitting around with nothing to keep her mind from wandering. She grabbed her purse from the bed to get her phone. She would call her father, maybe he would be able to comfort her, even though she couldn't really tell him what was going on with her either. Annie loved her father, she really did, but there were certain aspects of her life that she rather not share with him in too colorful detail.

She sighed when she saw the flood of new messages on her phone. There were at least six texts from Celeste – all of them pictures of her in various party outfits. Where the hell had she gotten a 'Stars and Stripes' sequin dress? Annie could've sworn she didn't have it with her when they had packed last night. Maddie had sent a picture of herself in front of the Eiffel Tower in their group chat that Celeste had aptly named “Constance Royal Court” after Rachel Cavalli had crowned her new Queen B at the end of their sophomore year. Then there were the three messages Quinn had sent her earlier and that she had ignored.


Quinn Davenport (2:25pm): We need to talk.

Quinn Davenport (2:25pm): Please.

Quinn Davenport (2:26pm): I'm coming over.


Looking back now, she probably should have read those texts. There was another message from him. It was a voicemail, dated 3:47pm. He must've sent it right after he had left. Her finger hovered over the message, unsure if she even wanted to hear it. What more was there left to say? She took a shaky breath and hit 'play'.


Hey... You probably won't even listen to this, but I- I don't know... I guess I just wanna apologize. For showing up at your place like this. For trying to make you talk even though you said you weren't ready. But the thing is, Annie, I am ready to talk about this. I have been ready to talk about this for over a month now. And I know you feel guilty, Annie. I'm feeling guilty, too. But we can't just ignore what happened. Annie, we slept together and all the silence in the world isn't going to undo that...”




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