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When you walk right by
You're falling hard, and you're taking me under
I can't help but try
Things I miss keep haunting my mind

-Holiday Parade "Hope Dies Last"

You never forget your first love until she forgets you.

Nate Archibald often wonders why the girls he wants always seem to change for him. He goes after them when they are one thing only to have them turn into something completely different.

He is eighteen years old on the brink of something bigger when he comes to the realization that perhaps he is a ruiner. He ruins girls like his father ruined his mother and their family. He ruins them like Grandfather has ruined him.

He is first attracted to Serena van der Woodsen's long blonde hair and slightly awkward laughter. She was always getting herself so dirty, dresses drenched in dirt and fingernails caked with pollen, but her hair stood out shiny and bright nonetheless.

She is the first of all of them to kiss anyone. It's the summer before seventh grade and it's with some asshole named Carter Baizen who's in high school and Nate doesn't think he's ever been so mad in his life.

Carter's the first boy she kisses that night, but he's not the last. Nate loses count soon after.

Serena is flighty and indecisive and spends her time at parties with older guys that don't invite him anywhere, so one day he notices her best friend.

Blair Waldorf is unfailingly perfect in every single way. At first, she scares him, but once he talks to her, he finds she is just as nice to him as Serena, if not nicer. He notices she's not very pleasant to other people in their grade at St. Jude's and Constance, but it's her smile that makes him forget this irrelevant fact.

Blair is particular about what she likes and how she likes it. When he tells his parents about her one night at dinner, they eye each other over the dinner table and smile. They tell him something about the Waldorfs being a good family, but he doesn't listen.

That night, he dreams of Blair's soft hair and bright smile.

Blair becomes stuffy and lackluster with each passing day, so Nate finds himself drifting back toward her best friend. She's crazy and lacks inhibition, so when they're drunk together at the Shepherd wedding, they finally let go and into each other.

It's sloppy when he removes her gold dress, but when he slips into her for the first time, he feels no guilt because she feels so perfect to him. It's later when she's run off and he's semi-sober that he cries because it has to be the first time he's hurt Blair. It surely won't be the last.

Serena runs away to Connecticut, but Nate has nowhere to run to but Blair's unsuspecting eyes. They haunt him with each passing day as she dotes on him like nothing is wrong. He becomes distant, the worst boyfriend she could ever have. He doesn't deserve her and he knows it.

It would break her heart for him to tell her and he can't do that to her even though he thinks he loves Serena, so he closes his lips when she opens hers, and it's semi-easy to kiss this girl when she wants you so badly anyway.

His night with Blair is even better with his night with Serena and this leaves his head spinning with unbridled thoughts. She's not wild outside of the bedroom, but she's tempestuous inside of it, and it's definitely beyond any of his dreams.

She fits comfortably against him, more comfortably than anybody else. It's like his shoulder was made for her head when she rests it against him. She falls asleep first, content. He wonders who gifted her the necklace currently on her thin, graceful neck.

Blair turns out to not be who he thought she was when she sleeps with his best friend first, so he locks his heart away. One day, Vanessa Abrams finds the key.

Dan Humphrey's best friend is witty, her humor biting with sarcasm. She's different than Blair and different from Serena and she's just the distraction he needs from these Upper East Side girls that have seemingly torn him apart.

They learn about each other over coffee at a small diner in Brooklyn overlooking the bridge. He tells her about his father and she tells him about art and making movies and Hungarian food and they have nothing in common, but this doesn't bother him.

He's maybe not over Blair like he thought he was when he sees her so put together at Bart and Lily's wedding. It's the affair of the century thus far and she's beautiful in pink and white. He's with Vanessa who's so different in her vivid orange paired with turquoise jewelry.

The difference is partially why he was first attracted to Vanessa, but he doesn't feel her pull as he glances at Blair's dark, pulled back hair. She's wearing one of those headbands she always is and he feels the strange urge to touch it.

He breaks even more when he's outside and his best friend spills his heart about Blair and loving her and all he can do is think about what an idiot he is. He had one of the greatest girls in the world, if not the greatest, and he let her go. He thinks he may be more like his father than he thought.

The summer is rampant with sex and these new non-feelings and older women named Catherine. He should feel guilt that she's married, but he's so indifferent at this point that it doesn't hardly matter. She's even more upper crust than his mother and he thinks she's the same age as his mother, but he's already halfway down the path anyway, so he gives in because it's easier. She dresses him in Ralph Lauren Purple Label without a second thought and they walk in together as mother and son and no one's the wiser.

He begins a fake relationship with Serena which would have thrilled him many months ago, but now just leaves him depressed and aching for companionship. She's even sadder than he is over her breakup with Dan and she spends her time moping around her grandmother's Southampton house like nothing is ever going to be alright again. He isn't sure he feels differently.

Nate's kicked out of the townhouse that he's always called home and barely sleeps each night. When he does, he dreams that he doesn't sneak back into the first floor like he doesn't belong there.

Dan Humphrey is a meddler and he's never much cared for him, but he's a good guy with a good heart when he offers him a place to stay. He refuses at first because he is an Archibald (what good was that now?) and a Vanderbilt and combined, these family names make up a predominant hold on the upper crust northeast.

It's easy to live with the Humphreys. Dan is awkward and talkative, but he's always been awkward and talkative. Nate wonders what Serena ever saw in him until one day, he becomes his friend. Jenny is scarce, working for Eleanor and then not working for Eleanor and then designing her own line and a host of other things he can't keep up with. Rufus is a kind man who always knows what to say and when to say it. His love life isn't as together as his regular life and Nate thinks that maybe one day they will come together for him to be happy.

He notices Jenny one day when she wears severe bangs and a cocktail dress so short it's almost indecent. Her style is nothing like Blair's (although it used to be, because Blair was the one training her) and a little like Vanessa's and it's easy to kiss her when he thinks she's being taken advantage of by some college age photographer.

Jenny Humphrey is not as innocent as he thought she was when she pulls out old claws to make them fresh and humiliates Vanessa at the Snowflake Ball. Her blue eyes are wide with fright (so unlike Serena's) as she tries to touch him and apologize, but in this moment she is so eerily suggestive of Blair's worst behaviors that he can't stand the sight of her.

He runs to make sure Vanessa is okay, but she leaves like this isn't awkward at all. He looks between the girls and sees the mess he has made of their lives and he isn't even sure how this came about in the first place.

It's easy to get along with Vanessa when she opens Nate's eyes to life beyond Central Park South. They've done the Brooklyn thing already, so she shows him parts of Manhattan he's only heard about through the grapevine. Greenwich Village is cool with its host of NYU students and yuppies after work. He's a little less comfortable in her favorite Lower East Side, but she loves it so much that he pretends to not care.

He's surprised to see Blair with Carter Baizen one day. He wonders what the hell she is doing and wants to stomp across the bar to punch Carter in the face (again) before he realizes that this girl is not his and he can't take her away. She's laughing at something Carter tells her before he places a hand on her thigh. She looks at Carter's eyes with her own and Nate can't tear his eyes from her.

Things with Vanessa are slowly going to shit (this always happens to him, so he's used to it by now) when he begrudgingly patches things up with Grandfather. The Connecticut estate feels cold to him for the first time since he's been coming here at age three.

Grandfather talks him into an internship at the mayor's office and before he can say, "No, I can't, I'm going to Eastern Europe with my girlfriend to eat weird Eastern European foods," he finds himself agreeing to the idea.

Vanessa is disappointed when she hears the information from Tripp, but Tripp's always had a big mouth anyway. Nate stares at Blair when he gives a speech at the manor, the only one that seems to understand what he is going through. He is a Vanderbilt, that much is for sure, and it is time for him to step up to his destiny and take control of his future.

Blair is so sad when he finds her on the balcony and he wants to talk about Yale and Carter and Chuck, but something in her eyes tells him these subjects can wait. She asks nothing of him, only leans her small head on his steady shoulder. When she begins to nod off, he becomes her gallant knight and takes her home.

There have been many nights like this, with a tipsy Blair on his solid shoulder in the back of a town car on the way to Manhattan. It's been a while since they have occurred, mostly because they haven't hung out since they haven't dated and a little because she can hold her alcohol (slightly) better now.

He kisses her head and inhales her scent before he begins to carry her out of the car. They've reached Fifth Avenue and her penthouse, but she stirs, insisting on walking by herself. He's not sure when Blair Waldorf decided she didn't need to be rescued, but there is no way he is deserting her here. He's not sure what brings this on, but he's done forsaking her like she's not good enough. She's always been good enough and he starts to believe that maybe he is the one that doesn't deserve her.

Nate decides he can be chivalrous when he walks his ex-girlfriend through doors he knows better than his own, but when they reach her bedroom and she looks at him with those eyes, he can't say no when she reaches out her hand and says, "Stay."

Nate still can't trust her even though he tells himself it's all Chuck's fault so he gets a lease on a place in Murray Hill that she's bound to loathe, but he wants to hold onto her so badly this time he does it anyway. It hurts him more than he thinks is necessary when she decides to scheme with Chuck and uses Serena as an excuse to get away from the apartment, get away from him.

He thinks it can't be natural to want to plot someone's destruction when he asks her something as serious as this. She freaks out and leaves and ends up in the arms of his best friend. Chuck is waiting in the limo like he always is and he has the biggest smirk on his face that Nate wants to wipe off so badly.

There's guilt and shame on her face when she returns from a night with Chuck, but she looks sadder than anything else. She was always so sad. He asks what's wrong, but she apologizes for the night.

"It's okay," Nate whispers, "I'm just glad you came back."

He takes her into her arms and breathes in her hair, a soothing scent for him, before saying, "I love you."

It's not enough for her because she crawls into Chuck's willing arms when he calls on the first ring. Nate's against it and Serena's against it, but since when did she listen to them? Blair was the most stubborn of them all and she's more than a little bitchy when she becomes herself once more.

Chuck forces thoughts into Blair's head that should've been there in the first place—about the apartment, Nate, and trusting her—and Nate wants to tell her Chuck is wrong and deluded, but instead she insists on telling him how she let her head get so cloudy she couldn't even make a proper judgment.

He finally feels how she must've felt when he had the thing with Serena and he closes his eyes in pain. He wonders how she put up with it for an entire year. Maybe she was stronger than they gave her credit for.

He's almost begging her to stay and she closes her eyes until he utters, "Blair, how can I love you if you won't let me?"

He's right and it hurts and something inside her finally gets it so she walks toward him and throws her arms around him.

He's still looking at her warily, so she murmurs, "I'm sorry. I'm ready to try." She glances around the bare apartment and mentions, "I'll have to call my interior decorator."

Blair screws it up again when Gabriel dashes with all their parents' money and she uses it as an excuse to get away from him. Nate knows her better (finally, he thinks) and calls her out on it, but she can't take the confinement anymore, so she leaves. For the first time in his life, he follows.

They're far from perfect and it's about time they both decide to try. When she takes his hand, they help Serena together. In this moment, he's never felt better than he does now. He might lose a best friend, but he'll gain a girlfriend and a life with this girl that maybe isn't as ruined as the others.