Sinking Sailboats, a gossip girl fanfic

A/N: This is very angst-y, a little bit dark, and it hits upon a touchy issue. I originally intended this to be a Serena/Tripp fic, but it took on a life of its own. Reviews are very much appreciated, and if you're interested in reading some S/T, let me know, because I feel like I might want to write them in a less depressing tone at some point in the near future.

Sinking Sailboats

Sometimes, what we call love

is just a settling of scores,

or a seeking of forbidden pain,

or a circuitous path

to the kingdom of cruelty,

or she simply might have

confused lack of capital

with heroism

while searching for rescue

without knowing what from.

-- Anne Roiphe

He is almost Nate.

Not quite, she knows. Not really, not at all.

Playing pretend was always Blair's MO, hyping it up, forcing her mind to twist (you are in love, it's him, and it's forever). And she used to scorn it, worry about it, her life was too enchanting already to bother making things up. But now Blair is in love, and it's him, and it's forever, and Serena's starting to realize that playing pretend is just easier sometimes. Sometimes there is no happily ever after, sometimes there's just a wasteland, a battlefield of causalities all of which she herself has caused, even her own. For all her adventurous spirit, she thinks she might be a bit of a coward at heart. She needs it to be easy now, because she just can't deal with the hard things anymore.

She doesn't return to New York often, because the Upper East Side is the territory she once reined, the landscape for her (their) days of glory, and also the catalyst for how far she's slipped. She is still thin and tall and beautiful, she's still got that mildly selfish, charming quality. She is still Serena van der Woodsen, she is still envied by all without really realizing it. But she can feel her greatness slipping away. Her peers are settling, into work and social functions, marriages and families. They all do it so easily, so naturally, even Chuck and Blair. Serena, alone, struggles with it all. She lives in the moment, focuses on the present, and she can't quiet excel at his as effortlessly as she does at all other things. She works (intermittently, almost casually, but well) and five men have proposed to her (the hope and anticipation dashed in their eyes the moment she sighed and pressed her lips together). She's had her chances.

But that's not what she wants. In total honestly, she misses her youth – this is what she tells herself, this is how she plays pretend, because missing adolescence is easier than missing him. She isn't old, by any means, she's twenty-seven. This should be the beginning of her real life. But she doesn't want that reality; she misses summer afternoons and stolen kisses and laughter that blended so perfectly with her giggles. She misses a certain set of eyes following her legs when she wore her Constance Billard uniform skirt and her favourite soft brown boots, she misses the way a certain set of arms encircled her, picked her up off the floor. She misses chances, and it pulls at her optimism, at her joie de vivre, and she finds she doesn't like adulthood as much as she thought she would. It is empty; she never had a whole, but now she is without even the halves, pieces, fragments that were always in her grasp.

When she sees him, it's at one of her old favourite bars, fairly quiet in the lobby of an upscale hotel. She feels her lips curl upward slightly, air flooding her lungs, a little bit of the light going on again, brightening her blue eyes. He looks somewhat how she feels, so she doesn't hesitate when she slides onto the stool next to his confidently, resting one elbow against the cool marble counter of the bar and propping her chin on her hand, smirking sweetly.

"Hey, you," she says, unable to help the thread of affection that seeps into her voice. He's a sight for sore eyes.

He starts, looking up at her, and a smile – not quite a grin, but almost – springs to his lips the moment he recognizes her. "Serena van der Woodsen," he says lowly, his eyes wrinkling around the edges. "Gorgeous as always."

She laughs – almost giggles – and bites the corner of her lower lip. "Tripp," she greets him, her eyes skimming over her face as he signals over the bartender and orders her a drink. Her eyes sting as he glances at her for confirmation that she still prefers vodka in her martinis, not gin. She nods.

He is achingly familiar, and her heart seems to convulse in a way she hasn't let it in years. He's almost Nate. She doesn't want to think it, but she can't help the way it happens. He is more man than boy, more Vanderbilt than Archibald, darker hair and deeper eyes, older and maybe wiser, but…almost.

"What've you been up to?" he asks her casually, and if she tries hard enough she can ignore the thickness, the maturity in his voice, and that easily notable tip-toe quality, afraid of sparking something within her. She's heard it for years and it makes her feel naked, stripped down, her emotional turmoil revealed. "I hear you've been living quite the wonderful life."

She blows out her breath and reaches over, pulling his glass lightly from his hand and taking a drink, as her martini hasn't yet arrived. "My life…" Life. She trails off and he doesn't push it, watches her expression in his peripheral vision instead; he must see the dazzling smile she forces onto her lips, the one that used to sit there naturally. "What about you?" He's heir to a vast fortune, well-recognized in the city. "Work? Wife? Kids?" she chirps.

"No kids," he says simply in reply, staring down at his drink, the print her lipstick has left on the glass' rim.

Her smile fades, but only in her eyes. "Are you hiding here?" she asks teasingly, trying to recognize everything he leaves unspoken, her stomach tightening.

He cocks his head slightly to the side, his lips curving into something that lingers indecisively between a smirk and a sneer. "Are you?" he asks her back, no mirth in his voice.

All it takes is a little alcohol in her system; the flash of a credit card emblazoned with the Vanderbilt name. Her hair is falling around her shoulders and his shirt is unbuttoned before they even leave the elevator. She lets it blur, like she used to, the sound of her shoes hitting the wall when she kicks them off, of a zipper being dragged down by her fingers. She closes her eyes and tries to feel instead of thinking. She lets herself believe that his hands are as accustomed to her skin as they feel, lets him unravel her, and responds with a ferocity she hasn't dedicated to sex in a while. She forces herself to ignore the smaller, painful things, like the way his body fits so closely with hers but not quite perfectly, the spot that he kisses on her neck that's off by an inch, and the way his hands tug at her hair just a little bit too much. She bites her lip, hard, to force herself not to say another name and let's herself revel in the fact that it's almost exactly right. It's as close as she will ever come.

She's done this before, countless times with countless guys. She's not proud of it, not really, but she is searching for something impossible to find. And it's given her experience, let her know the routine. She takes a moment to breathe, his forehead pressed to hers momentarily before his lips ghost over hers, and she opens her eyes to look at him. Her body feels heavy, stuck to the expensive sheets, stuck to him. This is the part where she leaves, with his consent or not, whether he's sleeping or chasing after her, whether he kicks her out or she kicks him away on the way to the door. This is the part where they pull away from each other, giving her the space to reconstruct herself before she flips her hair and finds her smile and puts her hand on the doorknob, twists.

There is a moment where the world seems to still, where there eyes meet and she licks her lips, tasting blood. Her throat aches and her heart jumps. She's torn between something like revulsion and something very close to comfort, lying in bed with this man. Tripp rolls slightly toward her, cupping her cheek in his hand with surprising tenderness, and kisses her. When their lips collide it tastes metallic, iron and regret. She finds herself curling into him afterward, his arms wrapped tight around her, the steady thump of his heartbeat under her ear. She's lost track of how long it's been since either of them have said a word, but somehow that primary organ speaks for him.

It's not supposed to be anything. She's lost and he's trapped. He hates his movie script ending and she hasn't got a fairytale. One afternoon in a hotel room, satisfying sex, kiss his cheek and say goodbye. There is no option of love.

But underneath the surface, it lingers there, threatening and enticing all at once. Togetherness supplies such temporary release and relief. They're stuck in a place that doesn't allow them to be together, but if they make an effort, it can almost seem real.

Being the other woman isn't exactly foreign territory to her. She did it all her life, didn't she? The older they grew, the less Nate became Blair's and the more he became hers, an emotional affair. He had the title of Blair's boyfriend, but Serena had his heart. And slowly, overtime, it became deeper and deeper until they pushed into the realm of physicality as well and completed their betrayal.

Seeing Tripp with his wife – which she does, occasionally, now that she's set her roots back down in New York society – does not make her ache the same way she used to when she saw Blair with Nate. She doesn't know Maureen, doesn't care about her unstable emotions the way she used to for Blair, doesn't really give a damn about her socialite, head-of-Whitney-Committee life. Seeing Tripp hold his wife's hand doesn't sting like seeing Nate look at Blair used to, because she doesn't feel that same pull of longing.

Masochistically, she misses it. She's always been good at making trouble for herself, so she does. She gets herself invited to more of the same parties, visits the Vanderbilt estate and charms Tripp's grandfather like she's always been able to do. She gives him smouldering looks across the room and relishes the burning feeling, hot jealousy, she gets when she sees Maureen smile sweetly at him before pecking his lips. She likes the uncomfortable shift in his smile when she lets her hand linger in hers when she goes to say hello, the noticeable intimacy in her voice as she says "Hey, Tripp." It all makes her feel more alive.

(Almost like he's there.)

Despite his cheating, and the way her smiles never seem quite as bright anymore, there is something easy, relaxed and uncomplicated and (almost) pure about their clandestine relationship. She likes the pattern of it, the calm provided by the predictability, and the light rush of adrenaline it gives her. Her life becomes one of hotel keys, of subtle touches across Upper East Side dinner tables, of closets and midday encounters. Often she ends up waiting for him, but her impatient streak has faded away over the years and she doesn't mind it. She likes it, in a way. She'll trace the edge of the counter at the bar with her index finger or study her reflection critically in the bathroom mirror of a hotel room, and she can almost convince herself that she's waiting for someone else.

She was so alive, once upon a time, with non-stop energy and such a lust for experiencing the world. She was even more beautiful, wild and untameable, and a smiling pair of sea-blue eyes would follow her every move, like she was a drug, like they wanted that freedom she possessed, like their owner wanted her.

Now she's content to spend her days in her hotel room with the curtains drawn shut so tightly that no sunshine can invade her space. She closes her eyes and curls up beneath the sheets and wonders what it would be like to never get up, to let herself fade away.

Inevitably, he finds her in the darkness, flipping on the overhead lamp and flooding the room with artificial light. She opens her eyes, wakes up, keeps going. His hands skim down her back, tracing over the curve of her spine, and he slips out of his shoes as he lies on the bed with her. Mechanically, easily, she undoes the buttons on his dress shirt, presses her lips against his. He groans and buries his face in her neck.

"Serena," he says against her skin, reverently, like she is so beautiful and so sexy that he can't stand it. He rips her shirt, accidentally, and she wraps her arms around him, closing her eyes again, against the glare of the light. She doesn't mind it, really, the exposure of florescent bulbs, because for once she doesn't have to pretend.

He wants her, pressing kisses against her neck in an uninhibited way, and she internally instructs her body to want him back. Somewhere in the very back of her mind, somewhere that the stinging blaze of the light bulbs in the chandelier on the ceiling can't reach, a childish part of her misses the sweetness in the voice that used to tell her she was pretty.

They reach a strange point of their relationship, a point that would make it truly authentic if it weren't for the lies they're both telling to others and to themselves. They are noticeable people, even more so together, but Serena knows the hide-outs of this city, the sacred spaces. She takes Tripp to those places and it doesn't feel quite right, but she takes him anyway he holds her hand and kisses her forehead and treats her like a girlfriend. She has the passing thought that places like this deserve footsie games under the table and nicknames and toothy smiles over top, but it would sound absurd to call him Trippy (it tastes ugly and strangely comedic on her tongue, just the thought of it) and they are too old, too jaded for playful flirtation.

The air is tense around them, she knows he's uneasy because he gave her jewellery earlier in the day and he thinks she's upset, thinks he's trying to buy her off for being his mistress. She's not upset, she's borderline apathetic. She knows, somewhere beneath the propriety of his personality, he cares for her. The diamond necklace sits heavy around her neck, matched perfectly to the white dress she's wearing. She zips the pendant back and forth on its delicate chain absently, surveying the restaurant. All the eyes that were glued to her snap away, all but Tripp's.

She knows she looks stunning. When he picked her up he said, "You look…" and had stumbled, stuck in speechlessness, before blurting out, "…fuck." It had made her smile, real and big, that moment when he was so clearly smitten with her, when he seemed younger, when he let himself speak what exactly was on his mind.

Across the table, feet kept close to his chair, he clears his throat and tugs at his collar, nervous. He has a merciless quality to him (very much a Vanderbilt) but she sees some genuine emotion floating around in his eyes. "I know you haven't…you haven't said…but I could…if you wanted, maybe I would…" He isn't stuttering; he's just avoiding the hard words, just like the minor politician he is.

She shakes her long blonde hair out, tilts her chin, sips her champagne demurely. "You won't leave her," she states, her gaze drifting away from him.

He sets his fork down and reaches for her hand, and her fingers curl in, resistant to his touch. He looks at her imploringly, waits for her to say more.

Serena smiles her Lily van der Woodsen smile, impenetrable. "I won't ask you to."

She must be losing her edge, because she forgot that if anyone was going to find her at that well-hidden, quiet restaurant, it would be one of Chuck Bass' private investigators. She knows it's Chuck's doing because it's Blair she gets the call from.

Serena doesn't see her best friend much anymore, so little that she wonders if that title still really applies to the relationship they share. There is too much shared history, consisting of one person in particular. Dutifully, she answers Blair's second phone call because she knows that Blair will just keep calling until she does. She makes the trek to Blair and Chuck's impressive penthouse apartment in jeans tucked into her boots, trenchcoat-style jacket pulled tight around her, hair falling into her face, barriers against the inquisition she knows is to come.

Blair drags her inside, lightly, by the wrist, and sits her down. The very first thing she does is tuck Serena's hair out of her face. She looks alarmed – by Serena's vacant blue eyes, no doubt, a sight she herself has grown accustomed to – and she presses her lips together. Blair is particularly beautiful and lively; she's pregnant, carrying another life and a little extra weight, a glow in her cheeks and a maternal lilt in her voice.

"Serena," she murmurs, concerned. (People are always saying her name not quite the way she wants to hear it.) "Serena, honey, what are you doing?"

"I'm not having this discussion," she sighs, avoiding Blair's happy brown eyes.

"Sweetie, I know…I know you're hurting," she whispers, her words delicate. "I know that…that this has been very hard for you to deal with. I know that you're feeling…maybe a little hopeless, right now. But I wish you would talk to me. It's been a while since –"

Serena glares at her, a way she's never really wanted to glare at Blair, and the brunette stops short, mouth open, eyes wide.

Regrouping, Blair tries again. "You don't need to feel guilty. I know what it can be like to deal with…" She trails off yet again and blows out her breath, frustrated. "But –"

"There's no but, B.," Serena cuts her off, softening her gaze. "There is no other way for this to go, okay? Yeah, maybe you struggled and maybe you have your regrets, but they can't, they can't compare to mine; you're married and you're having a baby and you're…" She's got a perfect reality, she's doing it right. It makes some point deep in Serena's chest hurt.

"Yeah," she breathes. "I'm married and having a baby. And what's your future, S.?" Blair's voice hardens a bit. "Tripp? You really believe that? This clandestine romance, that's your version of forever? Hotel rooms? Closets? Sex, and that's it, you really believe that? You guys are going to do this into your sixties? Your seventies? Until you die. Serena, that's not a future. That's not a life."

Serena shakes her head, gathers her purse, and walks away from the joy Blair's exuding, doesn't turn back, wondering when it was that they switched places.

She abhors the thought of old age, such a separation from the happiness of her youth. She doesn't want it, doesn't need it, refuses to acknowledge the future. She crashes into Tripp's house – Maureen is gone, she finds, but she wouldn't have cared either way – stripping off her jacket and her boots, straddling him on his office chair. She notes his surprised smile and kisses him fiercely, begging him with her body to make her feel young again.

Sometimes whatever they have feels so fleeting to her, like when she looks at the wet footprints from their bare feet on the floor of the bathroom after a shower, waiting until they dry and fade away. She feels something big for him in those moments, but that, too, is fleeting.

The days when she's almost happy, she always gets a message from Blair, as if it's been calculated that way. (And maybe it is.) They get more and more desperate, more and more annoyed, more and more worried, more and more gentle. When B. starts dropping thinly veiled hints like "I heard Humphrey's got a book signing in the Village" and "Carter Baizen's staying at the Palace", Serena knows things must be truly fucked up in her life. She laughs it off, decides not to care.

But she almost does.

She can bring strands, little hints of a boy she used to know out in him if she tries hard enough, and suddenly she's got new bursts of energy that she dedicates solely to him. He's enthralled by her, her sudden surge of vivacity. She's more passionate with him in bed – or wherever, up against a wall, another one of those closets, and maybe most importantly on a bar after closing. She's something like happy again, and her smiles don't take quite as much effort and her clothes get brighter and her heart feels fuller.

They get lattes together the morning after they have sex at that bar, and her body is buzzing. He gets a smear of whipped cream on his lips and something in her cracks, then melts, and she kisses him right there on the Brooklyn (it's safer) street. It surprises her, how genuine it feels when her arms twine around his neck and his hands land on her hips, pulling her closer. He kisses her back, right there in the street. It feels good.

They're using each other. They never hid it, never denied it, but they never talked about it, either.

It scares the hell out of her when she starts to see something strikingly legitimate in the emotions in his eyes, when she starts to feel the same things fluttering around – lightly, so lightly – in her own chest. It is almost, almost, the same something she thought she'd never feel again.

So it is a mixture, split fifty-fifty, of regret paired with relief the day the tabloids leak a photo of them kissing over lattes on the street and Maureen finds out.

His wife is the perfect socialite wife, doesn't kick him out, doesn't make a scene, doesn't comment on a thing. She keeps him in her home, keeps calling him her husband, with the quiet, unspoken condition that he will never see Serena again.

She has no bitter feelings toward Maureen. She cracks the blinds of her hotel room, examines her reflection, waits for no one. As she watches TV and flips through papers from work, she wonders if she would do that, if she would gather up some false strength and fake dignity and let her husband get away with it. Either Maureen is a classic WASP, or she really does love him. Serena can't quite comprehend either.

The first night she spends alone without any possibility of seeing Tripp again, she dreams of sinking sailboats. She wakes up to the trill of her cell phone; it's Chuck calling her for once, not Blair.

She has a niece. An impossibly delicate, gorgeous little girl named for Chuck's mother. She takes Serena's breath away.

They name Serena godmother, though she doesn't think she deserves it anymore. Once she would have been perfect for the job, full of crazy fun for the little girl in her care, the perfect guardian should anything ever happen to her parents. She doesn't understand how Blair and Chuck can still trust her this much, because it's been a long time since she's trusted herself.

Baby girl Bass does not have a godfather. The space remains empty, a silent acknowledgment, and Serena ends up crying on the hallway. Chuck joins her there, his eyes raking carefully over her weary, tear-streaked face.

"I can't be her godmother," she whispers.

"You can," he tells her firmly. "Both of you need this; both of you deserve it. She'll love you."

She shakes her head, pushes away from the wall and wipes at her cheeks. She feels old all of a sudden, so tired of her life, which stretches out in front of her much further than she'd like it to. "I can't be one half of something that doesn't exist," she hisses into the sterile hospital hall.

Chuck takes a deep breath and meets her eyes, his gaze steady. "But S.," he says, words light but loaded, "Isn't that exactly what you're doing?"

Two weeks after her niece is born she is sitting in a doctor's office, tapping her foot impatiently against the floor. She is energetic again, nervous energy, the threatening kind. She bites her lip until she tastes blood. It's too silent here, and Blair's words from months ago are echoing around in her head. This is not life, not as she wants it. This is not, will not, be her future.

Only moments after her doctor, a woman with a reputation among the residents of the Upper East Side for her covert practice, confirms the result of the home pregnancy test she took three hours earlier, Serena's heels are clacking against the tiled floor as she strides toward an abortion clinic. It's stifling, the air heavy, and she can't breathe right. The receptionist gives her a tissue for her bleeding lip and she reminds herself to think, not feel.

When it's over she's startled to find Chuck in the waiting room, his eyes panicked. She has to have someone to drive her home, with her hazy mind and the cramping in her lower abdomen, and since she didn't put anyone on her admittance forms, that apparently granted them authorization to call her emergency contact. His eyes are aching on her behalf as he wraps an arm around her and guides her back to her hotel and up to her room, and she lets him grieve on her behalf because it is so much easier to twist her mind, to pretend it's not her loss.

She wakes up in her hotel room, artificial light on her skin from the lamp by the bed, and Tripp is there with a sombre expression on his face. He was undoubtedly threatened within an inch of his life by her stepbrother, she knows. Her vision blurs, and for a split second she has the urge to smile, because behind the coat of the tears in her eyes he almost looks like someone else.

Tripp's fingers slip through hers and his expression almost breaks her heart, or it would, if there were anything left to break.

"Do you want to talk?" he says, and she realizes that there is dampness on her pillows behind her ears, from tears slipping down her cheeks in her sleep.

She shakes her head. Long ago, she gave up on blonde-haired, blue-eyed babies with mischievous smiles and sweet giggles. She does that have to mourn this child, she's done that already; in a way, she does it everyday.

She's defeated. Serena van der Woodsen has most certainly fallen from her pedestal, has purposefully tossed away her crown. Whatever she wants from her life, she's sure it doesn't exist anymore.

It's strange how she still exists, even when she feels so broken, so empty and lonely. Sometimes she's sure she's only got half of herself left. She is hopeless. It's a sad word, and her pride has kept her from acknowledging it for this long, but there is no alternative left. She is still appealing to the world, her wit and her beauty and whatever it is that she has, but she doesn't feel it anymore. She doesn't feel much of anything.

Switching hotels for the first time since she broke up with Tripp, she moves into a drabber one, recalling those once-upon-a-time, runaway-and-scorn-all-money, live-with-nothing-but-love fantasies of her (their) childhood. It is closer to a graveyard. She starts having those same dreams, sailboats tossed about by storms, blood in the ocean. When she wakes up she finds herself dimly missing Tripp, who had some of the same DNA, some of that same blood pumping through his veins.

She wanders through the graveyard like some tragic heroine in the novels Blair reads, or used to read, anyway. Everything she once knew so solidly feels fuzzy and distant. She moves slowly, weaving in between tombstones. They tell stories of the lives that are gone, empty bodies buried beneath the earth, but such simple ones, dates of birth and death and relationships.

It makes her angry, as she carefully makes her way to the headstone she knows best, giving it a wide berth until the last possible moment. It says so little about someone who meant so very much to her, says so little about everything he cared about; it states facts and it even lies. She sits in the grass, because she's never cared about things like stains. She touches the ground, as if she can convey some meaning through it, and reaches out with the shaky fingers of her other hand, laying three of them on the letters that spell out beloved son, covering the second word, letting her eyes linger on the first. Be. Loved. If he has neither, she doesn't deserve them.

This is where she is. This is what it takes the break the unbreakable, untouchable girl. This, something that she denied feeling all her life, something which beat and broke and torn apart her heart, snatched all her chances away.

This is a life that is hers, but not his. A life that almost could have been theirs.

When she finally gets up to leave she finds herself stopping short, hands falling to her sides. Tripp is standing, sympathetically, a few feet away from her, and she can tell just by looking at him that he's finally understanding (he is just so close, this man in front of her, to the one six feet beneath her, so very close) and that he has left his wife (for now, at the very least).

He walks toward her and she makes her feet move, her heels sinking into the ground. He makes it two-thirds of the way and she manages to finish the last few steps, meeting him somewhere on her side of the middle. It starts to pour rain, thunder crashing and lightning crackling against the sky, like something about of a movie, the kind she can't watch without getting teary-eyed.

He kisses her, hands on her cheeks in the rain. It takes a moment, but she gives in and kisses him back, lets herself keep playing pretend, desperate to forget where they are at this moment and why.

It is grasping at perfection, the moment, the kiss. If they weren't standing exactly where they are, if he were someone else, abandoning the rest of his life and coming to save her, dropping everything for her because he picked her above all else, coming to whisk her away. It would be perfect.

And it almost is.

(Almost.)