Everything I write now re: Gossip Girl is just so angsty because the writers of Gossip Girl suck and it's hard to ignore canon. Anyway, this isn't my best work but here goes:
Blair Waldorf runs away from her first wedding because she realizes that she’s married an imposter, that she’s made a huge mistake.
Blair runs away from her second wedding because she sees how it’s all going to turn out anyway; she knows that once again, she’s made a huge mistake.
“Just drive,” she tells the cab driver, She sees how he takes in her poofy wedding dress, her teary and puffy face. His face radiates sympathy but he wisely shuts his mouth and says nothing. Instead, he takes her to JFK airport.
She already has her passport, and after she changes into some more comfortable running away clothes (wearing an I [apple] NY shirt this time, she wonders if maybe she can start her own runaway bride airport boutique), she closes her eyes and jabs her finger randomly at the departure board.
Beijing. It was perfect and unpredictable, yet Blair was not in the mood to have to deal with an interpreter. She scanned the list and weighed her options.
As if on cue, her cell phone lights up with a text message from Serena. No one knows yet, but I don’t know how long I can keep this up. Blair can imagine Serena just flashing a dazzling, apologetic smile at the hair people who have wondered where she’s run off to, smoothing over any temporarily ruffled features. The Serena Sheen, Blair calls it. Sometimes her best friend’s infuriating talent to make it all about her comes in handy.
She quickly looks for the first flight she could reasonably make, and slaps down her credit card at the ticket counter. Before she hits security, she turns off her cell and tosses it in the trash can of a restroom.
Her plane takes off ten minutes before her wedding is supposed to start.
When she lands in Belize, she checks into a hotel and sends a simple email to Serena. Dear S, Please tell everyone that I’m sorry. I just really need to be alone right now. -B.
She hesitantly starts another email: Dear Dan.
There are too many emotions that she can’t even quite articulate, so she deletes the email and tries to forget about all the drama she’s caused in the past. No matter what, no matter who she’s with, she can never give her all to anyone. Commitment issues have been sneaking up on her quietly since she was fifteen, but Blair is not interested in therapy unless it is of the retail kind.
That’s precisely what she does. She buys clothes, she buys food, she buys necessities until there’s nothing left for her to buy.
She wonders, more than once, what life would have been like if she and Dan had managed to run away together after her wedding to Louis. She imagines that it would be a lot like now-a good idea in theory, but in practice was utterly messy and complicated. Running away was desperation, but it was just a mark of how bad things had gotten.
Things weren’t even that bad earlier that morning. She had her fears and doubts, sure, but she really believed that she could go through with it. When she had put on her wedding dress though, she suddenly felt frozen. She knew she wasn’t happy, it was clear on her face. She could imagine her future, and it wasn’t what she wanted.
You deserve to be happy. I know I’m supposed to be cynical and say that happy endings don’t exist, but they do. It’s what you make of it. And if you’re happy, that’s all that matters. Congratulations on your engagement.
The card had come with a small gift buried underneath the massive pile of engagement presents. He had correctly guessed that Chuck wouldn’t bother with the gifts, would never see the note.
Instead, Serena had silently handed Blair the opened card after her mother and the wedding planner had left. His gift had been exquisite salt and pepper shakers in the shape of cheese pieces: the queen and the king.
It was perfect, but not the defining moment that made her doubt.
Instead, as she had looked at herself in the dress in the mirror, she had thought about her children. She thought about what she would tell them when they asked about how their parents met and fell in love. What she would tell her daughter about waiting for the right person for the first time, what she would tell her son about treating his lady friends with respect. How she could possibly explain to them the dangers of toxic and destructive friendships and relationships without being a complete hypocrite.
She stays in Belize because she still doesn’t know the answers to these questions. What she does know is that she doesn’t know how to make their love story appropriate because it’s so twisted, and she had been blinded by love.
Nate finds her after a week and a half. Or rather, she suspects that he is sent.
“I don’t know Blair, I think he’s really changed,” he says gently.
She gives him a funny look. “You’re just saying that because you think that’s what I want to hear.”
“Isn’t it?”
“No.”
He reluctantly tags along with her as she searches for a vacation home. Blair ignores him when he protests that she can’t stay here forever, that she has to go back to New York sometime. He lets it slip that he’s here on a mission from Chuck and her family, but she’s not surprised.
“He actually wanted to send Dan,” Nate admits.
Blair is startled. “Why?”
He runs his hand over the kitchen counter. The real estate agent had disappeared outside in order to try and wrangle two other showings for Blair. The air is still as Nate speaks. “As a test. He thought…that maybe you two had run off again. When he realized you didn’t, he offered Dan first-class airfare and travel expenses to come get you. He thought that if Dan would drop everything and come to your side, you guys were in a secret relationship.”
“So he’s changed, huh?”
“Blair, you know he loves you.”
“I don’t think it’s enough,” she says quietly. “Is it?”
Nate tilts his head and gives her a sad smile. “You know I really did love you you when we were younger, don’t you? But no…it’s not enough. I wished it were, Blair. I never meant to hurt you.”
“Then you of all people should understand why it’s over.”
“I can,” he says, “but you shouldn’t be telling me this.”
Blair ends up buying a house in Belize. Her mother and her father refuse to lend her the money, but Cyrus and Roman quietly slip her funds in some sort of weird, Waldorf significant other united front way. It has its own private beach, and Blair spends three days painting the master bedroom the perfect shade of pale blue.
She flies back to New York and ends it on a bench in Central Park. Now that they’re no longer together, he’s cold…cruel, even, to her. She meets up with Serena afterwards and they watch movies, eat ice cream, and Blair cries.
She’s drained the morning after, but she knows what must be done. She sends Dorota and Serena to get her things and begins to write thank you/apology cards for the gifts she has to return. By the end of the week, all the presents have been returned….except one. One gift that should be returned personally.
She’s leaning against his door when he sees her and drops his keys in surprise. “What are you doing here? I thought you were in Belize.”
“Chuck and I broke up.”
Dan chuckles as he opens his door. “You ran away from your wedding, I’m pretty sure you dumped him.”
It’s instantly comfortable and easy, their interaction. She wonders if that’s not such a bad thing after all.
She follows him inside and thrusts the small gift bag at him. “I came back to take care of some things. Return a few things.”
He raises an eyebrow as he reads the enclosed note. “Hmmm... ‘Dear Dan: Thank you so much for your beautiful and thoughtful gift. The salt and pepper shakers would have made a wonderful addition to our kitchen. However, it is with a heavy heart that we wish to inform you that we have canceled our wedding and are thus returning your gift. Sincerely, Blair Waldorf and Charles Bass.’ Wow.”
“I didn’t know what else to write.”
“Well I know Chuck had no part in this note since you address me by Dan,” he says dryly. “You didn’t have to return these, you know. You should have just kept them.”
“They fit the Blair of Chuck-and-Blair, Blair-and-Chuck. It’s not who I am anymore.”
“So, who are you now?”
It’s not a question she can easily answer now. Instead, she spends the rest of the day in Brooklyn watching movies and eating takeout with her legs tucked primly under her skirt. He didn’t ask her to stay, but he doesn’t ask her to leave either.
Her life slowly creeps back to normal. She returns to work at her mother’s company, she shops with Serena, she terrorizes Nate’s new love interests, and she spends time with Dan.
She sees Chuck at parties, of course, and at Thanksgiving. He always has a new girl with him, and she knows that Lily has quietly taken measures to restrict his cash flow so he doesn’t waste it all on hookers and blow. She hears whispers that it’s her fault, that he had never gotten over how she had trampled over his heart.
Serena doesn’t mince words when she flat out calls her stepbrother a fucking loser. Granted, one that she doesn’t hesitate to bail out of jail when he needs it, but his life doesn’t fit in with theirs anymore.
On what would have been her first wedding anniversary, Blair is in Belize with her friends instead. Serena and Nate both leave early, one to California and one to Chicago, for business.
“So,” Dan asks as they sit together on the beach. “Do you regret it?”
“No,” she answers without skipping a beat. “I’m happy now.”
“Good.”
They sit in comfortable silence before she asks, “Do you worry about your writing career peaking while you’re so young?”
“It’s a never-ending fear,” he admits. “Sometimes I wonder if I use writing as a crutch, if it’s keeping me from something else. But I also love it too much to let it go right now.”
“What are you writing now?”
“A fictional memoir about an artist. My parents are helping me out a lot, actually. It’s been nice spending time with my mom.”
“My mom’s still mad about what happened last year,” she sighs. “She just doesn’t understand that it was hard for me too, but I had to follow my gut and my heart.”
There was a lull as the sound of the waves filled the air.
“You know what I like about you, Blair?” he says suddenly. “Is that even when I thought you were evil, you never did anything half-heartedly. You have such a passion, such life…it used to catch me off-guard sometimes. And you have so much heart, Blair. You should always trust it.”
The Blair she is now isn’t a brand new Blair, she realizes after Dan’s words. It’s just been someone who’s been there all along. Someone who is strong, loyal, fiercely devoted to those she cares about. Someone who isn’t going to let this opportunity go to waste.
“That note you wrote,” she asks. “Do you really think happy endings exist?”
“Maybe it’s cheesy,” he admits, “but yeah, I do. Why not?”
“So what would be your happy ending?”
He smiles faintly, embarrassed. “Well, this is pretty close.”
She kisses him, and it’s better than what she remembered. She knows that this isn’t a rebound, that she wants to be with someone who makes her want to be a better person. Someone who would believe that she’s going to be one, not someone who she would automatically look better next to by default. Someone that makes her feel genuine happiness, who would make the complicated times more bearable. Someone she could face all her future with, together.
Blair Waldorf runs away from her first wedding because fairytales aren’t always a reality.
She runs away from her second wedding because caring about someone doesn’t always mean that you’re in love with them.
She runs toward her third wedding, because he is the happy ending that she has chosen.