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There are days when outside your window
I see my reflection as I slowly pass
And I long for this mirrored perspective
When we'll be lovers, lovers at last
-Death Cab for Cutie "I Will Possess Your Heart"
Tripp Vanderbilt is twenty eight before he starts living for himself. It is at Grandfather's funeral that he finally comes to terms with everything he has been dealt thus far. As he gazes at his younger cousin Nathaniel, he wistfully wonders what it would be like to be him. He could've been like Nate – he could've chosen something else over Yale, severed ties with certain family members, and dated quirky brunette filmmakers from Brooklyn – although he secretly knows he might have only enjoyed two out of the three.
He is twenty eight when his wife Maureen sleeps with a partner at his law firm, making their marriage crumble under the weak foundations it had been laid upon. It's not long before he is offered a position at Sullivan & Cromwell and he makes the move to New York a little too easily, removing the white gold band from his finger before he leaves Connecticut for the last time.
Many of his Yale friends live and work in New York as well, so it's not hard to become reacquainted with them. It's hard when they invite him out in pairs – with wives and girlfriends and domestic partners alike – so he just shuts his eyes and wishes that he would've not listened to Grandfather and fallen in love with a girl on his own account.
He doesn't even know if he has a type anymore until one day, a young brunette stumbles into the office looking for advice on cross-border mergers and acquisitions. The information is for her ever busy father, but Tripp can't help but linger on her dark hair and slender legs. Maybe New York was the best choice for him, after all.
Nate's Columbia graduation is coming up and Tripp's never been an astute gift giver so he goes with the obvious and buys his cousin a fountain pen for law school. Pens were useful, he reasoned.
It's another thing entirely when he takes his place by Aunt Anne, only to have a giggle erupt to her right. Blair Waldorf is sitting next to his second favorite relative in a daring navy halter that gives just enough away.
He stares at her stunned until she begins to speak, "Sorry, it's just that we match almost perfectly," and they do, because he's wearing a charcoal suit with a navy button down and pocket square.
They make a pretty picture when Anne insists on snapping one and he becomes confused when the curly-haired girl from that one summer in Connecticut comes to sit by Blair and gushes something rapidly into her ear. Blair lets out another delighted giggle – he doesn't know if he's heard her laugh this much in the ten years they've known each other – and it unnerves him slightly.
"Tripp," Blair turns around, "You remember Vanessa, don't you?" and of course he remembers her more evenly now, even though her hair is longer and a little more tame.
They watch Nate cross the stage until it's all over and they get ready to celebrate.
Tripp doesn't know how he didn't notice before, but the family ring clearly adorns Vanessa's finger when he thinks it was meant for Blair's. At first, he'd thought the Nate and Blair saga had run amuck once more, but apparently Nate was once again choosing his own destiny instead of the one Grandfather laid out for him. It is times like these that make Tripp wish he was the more adventurous of the cousins, but he hopes it might pay off to one day be himself.
"So, what do you make of it?" Vanessa asks him, though he's unsure what exactly she is referring to.
"And you're referring to—?" he leaves the end of the question blank for her to fill in.
"Nate at Columbia, Nate with me, Nate not following the plan," she responds with a smile, and he has to give her more credit than before, because she's a lot more introspective than he once thought.
He shrugs with purpose, "Nate's always done what he wanted to do and everything he has because of it is his own doing. I can't say the same."
"Is this chastising or regretting?" she wonders.
He answers truthfully, "Perhaps a bit of both. Grandfather told me to go to Yale, so I did. He told me to marry Maureen, so I did. He assigned me a high ranking job in the Connecticut government before I got into law, so I did that too."
"You sound bitter," Vanessa mentions.
"No," he responds, but it's a slight lie, "Well, maybe. There were some good parts. I just wish I'd had it in me to choose my own path. I respect him for that."
She nods and lets him wander on his own to gather his own thoughts.
It's almost another thing entirely when he notices Blair sulking in the corner at Nate's post-graduation party. He wants to go and comfort this forlorn girl, but refrains when her eyes light up at the arrival of Carter Baizen. He sweeps her off her feet – quite literally – and they share their own private dance that they think no one else witnesses. They are wrong.
Carter is whispering something in her ear that makes her toss her beautiful head back and laugh, so Tripp tries to find something else to occupy his time because he feels like the creepiest of creepers as he lusts after his cousin's first girlfriend.
He chats with Vanessa because it is easy and she doesn't tire him with her petulant mannerisms. He speaks with several family members before he leaves, nodding at Nate and kissing Anne lightly on the cheek. He doesn't give anything else a second glance before he walks through the doors and back to his new life.
He starts dating the bossy brunette that hangs around his firm because she's one of the partner's daughters. She's physically beautiful, but she's imperfect next to Blair's eye-catching exquisiteness. Nevertheless, he takes the time to get to know her because she's trophy wife material and even though Grandfather is dead, Tripp is sure he is watching from above.
They're walking down Fifth as she tries to grasp his hand when she suddenly mutters, "You're not like Nate at all," which perks his ears because before now, he had no idea she knew his cousin.
"You know Nathaniel?" he asks.
She nods, "I went to Constance. His year."
And this information is too much for him because with it, she has to know Blair Waldorf. He wants to ask. He wants to ask so badly, but he knows the minute he does, this will be over. He's not sorry at all when he questions her about Blair.
"What about her?" she asks, as she crinkles her nose, "She made my life a living hell. And Nate's."
"Nate was better when he was with her," Tripp replies, angry at this girl for berating Blair, "God knows he can't function without her."
"Can you?"
"Can I what?" he asks, confused.
"Function without her," she replies languidly.
He doesn't say a word further and they break up as the sun sets against her long brown hair.
It's another two years until Tripp is thirty and he spots her easily across the room. He almost feels too old for 49 Grove, but his coworkers dragged him out after a fourteen hour day at the office and he couldn't be happier. She's sitting quietly sipping her bubbly champagne while her blonde best friend dances not five feet from her with two matching blondes that greatly resemble Keith Richards' daughters.
She's about to finish her glass when he walks up to the bartender and tells him to send the beautiful brunette in the corner a glass of whatever she was drinking before. The man looks at him incredulously, but nods, and twenty seconds later Blair looks surprised to receive a new glass. The bartender looks at her as he gives her the glass, nodding in Tripp's direction.
She doesn't hop off her seat or bounce when she comes to greet him, but she greets him all the same when she leans up slightly to kiss him on the cheek. He feels the heat burn on his face and it's not from the scotch he just ordered for himself.
"Come dance with me," she beckons, and he wonders who she has become because the Blair Waldorf he knew would never be this daring.
She drags him over by his tie, all the while delicately holding her glass in hand. He holds out an arm to spin her 'round and she lets out that delightful giggle he adores in return.
"So," she whispers in his ear, "I hear you dated Penelope Shafai. Ewww."
"Ewww?" he asks, "Aren't you a little old to say that?"
"Aren't you a little old to be here?" she asks, giggling again.
He's smitten and it's awful, but he takes her face with his free hand and kisses her anyway. She tastes just like he always imagined she would, like champagne and strawberries and so much rain. He wants to punch the guys in her life that have made her so unhappy, but he knows his cousin nearly tops that list.
"I could punch Nathaniel for almost ruining you," he whispers in her ear.
She doesn't giggle this time as she stares at him disbelievingly, "Nate didn't do anything. Besides, he has Vanessa now – and those terrors they like to call Veronique and Viktoriya."
"They're cute kids," he prompts, before she hushes him with a finger on his swollen lips.
She leans up again and he doesn't hesitate as he sinks his tongue into her waiting mouth. He feels his associates' eyes upon him, but he doesn't care what they're thinking for the first time in his life.
Tripp is thirty five before he contemplates marriage again. He'd already done the young married thing, the semi young divorced thing, and now he was ready to do the not so young married thing once more.
Blair is twenty seven, but happy when he asks her, but not before she wonders why it's coming so late.
"We've been dating a while," she nudges, but it's playful and that's part of the reason he loves her anyway.
He sincerely tells her, "I want this to be perfect."
There are tears in her eyes this time when she responds quietly, "It's already perfect," then, "You're perfect," but even quieter than before.
The New York Times
Weddings/Celebrations
Blair Waldorf, William Vanderbilt III
Published: November 3, 2019
Blair Cornelia Waldorf and William James Vanderbilt III were married Saturday at St. James' Episcopal Church in New York. The Rev. Brenda G. Husson, the church's rector, performed the ceremony.
Mrs. Vanderbilt, 28, is a managing director of PEI Funds, a venture capital and private investment firm. She graduated from NYU and Harvard Business School. She is a daughter of Eleanor Stetson Waldorf and Harold Waldorf of New York. Her mother is the owner and designer at Eleanor Waldorf Designs. Her father is a former lawyer now running a vineyard in southern France.
Mr. Vanderbilt, 36, is a junior partner at Sullivan & Cromwell. He works in the New York office. He graduated from Yale Law School. He is the son of Alexandria Bassett Vanderbilt and William Vanderbilt II of Greenwich, Conn. His father is an executive recruitment consultant in Greenwich.