If Gossip Girl Existed In 2018

Happy Gossip Girl Day, Upper East Siders!

Yes, you read right. It may have been six years since the final episode of the most epic show of all time aired on screens across the world, but the 26th of January is still officially recognized as Gossip Girl Day in New York. But that doesn’t mean the rest of us fans on the other side of the world can’t join in the festivities in our own way, right?

I’ll be the first to admit that, like many of you, I’m STILL watching it in 2018. Thanks or no thanks to Netflix who recently broke the internet by saying the show was going to be taken off the air soon. Luckily, it turned out to be false (or they changed their minds thanks to the thousands of distraught fans on Twitter).

I’ve recently begun watching the whole series for the ninth time and got to thinking about how different things would be if the show was still around now. Sure, the technology they use seems outdated, but on the whole, the show still seems fresh and relevant, even though I’ve watched it about eight times now. So I thought it would be fun to position the Upper East Side and all the characters we love so much in the modern world, 11 years after the show was aired, to see how they’d be getting on. This is just my take on things, though. If you’ve got your own theories, I’d love to hear them in the comments below.

If I were you, I’d go back and watch the last five minutes or so of the final episode of the series, just to give a few of the character lines I’ve written a little context, in case you’ve forgotten.

Starting with the most obvious fact, instead of flip phones, everyone would be using iPhone 8s, 7 pluses and iPhone Xs to communicate. If you needed to know somebody’s location, you’d just use Whatsapp instead of whatever ‘Loopt’ was and dating would be less about bumping into people by chance at fancy events, and more about finding them on dating apps.

The music and celebrity performances on the show would be from people like Dua Lipa, The Weekend, Julia Michaels, The Chainsmokers, Charlie Puth and Camila Cabello. The cast would make frequent appearances wearing Self Portrait, baker boy hats and carrying Gucci Marmont amd Dionysus Bags.

THEN                                                                                                   NOW

Gossip Girl

Whoever Gossip Girl’s new successor is has rebranded herself and now solely operates via Instagram. She plans her feed meticulously and alternates pictures of her gossip victims (always in the Hudson filter) with gossip tidbits in text form on a marble background with millennial pink or rose gold font. However, due to the Instagram Algorithm Change of 2017, you don’t get to see her posts unless you sign up for push notifications, so he / she will often ask you to click the three dots at the top of your screen, so the gossip updates stay relevant.

THEN                                                                                                   NOW

Blair Waldorf-Bass

Overworked as always, in addition to being a successful fashion designer and running her mother’s fashion house, Eleanor Waldorf Designs, she takes an active interest and holds a small but influential role in local politics, all while being going through IVF treatments for Chuck’s third baby. She now sports an elegant bronde ‘LOB’ and is friendly with (and often retweets) Chrissy Tiegan due to their mutual Anti-Trump sentiments. She is frenemies with Olivia Palermo, largely owing to the fact that their characters, personalities and career paths are so similar.

THEN                                                                                                   NOW

Chuck Bass

Chuck cleaned up his act completely and is now a loving, doting husband and father. He has expanded his hotel empire, becoming a big-time hotel tycoon with impressive properties in Europe, Asia and the Middle East. However, lately, as a calculated, pre-emptive PR move devised by his lawyers and media relations team, he is very publicly making sizeable donations to lots of charities, attending numerous ribbon cutting ceremonies and showing support for feminism on social media, just so he still looks good in the public eye in case the ghosts from his bad-boy past come back to haunt him in the form of women tweeting about him as their #MeToo story.

THEN                                                                                                   NOW

Dan Humphrey

Dan, in keeping with his brooding writer persona, grows a full beard and often sports a man bun. He turns his attention away from writing books and short stories and instead, sets his sights on writing Netflix originals and independant films. He and Serena move out to LA and he goes on to become a loving dad and a well-paid, celebrated Hollywood writer. However, rumours always fly in LA, and a new one has just surfaced saying he is working on a new Netflix series with his ex, actress Olivia Burke, and that sparks are flying on-set. But would he do that to our S? Only time will tell.

THEN                                                                                                   NOW

Serena Van Der Woodsen-Humphrey

The sunshine always agreed with Serena and she is loving being back in LA, this time with her husband, Dan and their little daughter they adopted from Cambodia, using Angelina Jolie’s adoption contacts. However, rumours have been flying, and to keep her mind off her husband’s alleged antics, she decides to launch her own exclusive mother and baby lifestyle app featuring articles on the best in designer maternity wear, healthy workouts and diets for expectant moms, organic baby formula, hand-sewn baby onesies from Paris and artisinal teething jewellery for infants. The #momterpreneur’s loyal readers and clients include socialites, royals, the Kardashians and Hollywood A-list moms like Victoria Beckam, Reese Witherspoon and Chrissy Teigan (who she is BFFS with). She often flies back to NYC for big events and to support the charities she patrons.

THEN                                                                                                   NOW

Nate Archibald

Six years ago, Nate was running to be the youngest Mayor of NYC. Sadly, he lost that election but continued his family lineage by working in politics and continued his work on the NY Spectator. However, he ran again in the last election and won! He has since sold the NY Spectator and has, instead, bought a football team which he is an avid supporter of. Rumours of him and Meghan Markle being an item surfaced the year before she moved to England to become engaged to Prince Harry. However, at the moment, he is dating Princess Beatrice Grimaldi of Monaco (Blair’s would-be sister-in-law if she would have married Louis).

THEN                                                                                                   NOW

Jenny Humphrey

We know Jenny started a diffusion fashion line at Eleanor Waldorf Designs called J by Waldorf Designs. However, in addition to her fashion line, she also has her own wildly popular Youtube channel and frequently advertises teeth whitening strips and weight loss teas on her Instagram, where she recently posted her own #MeToo account of ‘someone’ taking advantage of her on the roof at the Kiss On The Lips party. She is dating a distant relative of Prince William and Harry, who she met during her time studying design at Central St. Martin’s in London. Though, knowing Jenny, this would probably only be so she could have someone important photoragphed in one of her designs at a royal wedding. She takes full credit for Taylor Swift’s bad-girl transformation, and is vying for a privileged position in her squad with the likes of Kendall Jenner, Selena Gomez and and Gigi Hadid.

THEN                                                                                                   NOW

Rufus Humphrey

Rufus finally retires from his career making bad 90s music and he and his partner, musician Lisa Loeb, move to Connecticut for a more quiet life. Here, he turns his attention towards his other passion – cooking, and finally learns to cook more than just waffles. The couple open a little cafe in their neighbourhood (funded by his early investment in Bitcoin as advised by Chuck) where she takes the stage in the evenings (and he can’t help himself, so he always joins in). He was recently offered a book deal to write about life as the front man of Lincoln Hawk and all the crazy experiences he had, a lot of which involved Lily.

THEN                                                                                                   NOW

Lily Van Der Woodsen

Things didn’t quite work out between her and William Van Der Woodsen in the end (surprise, surprise). They are in the process of finalising their divorce, although rumours have been flying about her an a certain Saudi Arabian Sheikh she met whilst accompanying Chuck on a go-see of his latest hotel in Dubai. She is considering taking a break from her fast-paced life as a New York socialite and do the whole Eat, Pray, Love thing in LA, where she can find out what she wants from her life and help Serena and Dan with her new granddaughter at the same time (her way of making up for lost time with Serena and Eric when they were little). Or so she says anyway. With Lily, you never know what secrets are lurking beneath the surface.

THEN                                                                                                   NOW

Eric Van Der Woodsen

Shy, young Eric finally sprouts some facial (and chest) hair and really comes into his own in his mid-twenties. He jet-sets round the world and has his own luxury lifestyle boutique for men in the Hamptons making leather holdalls, lacrosse gear, preppy clothing and loafters with family emblem patch embellishments that have come to become his sigature. He is engaged to his Argentinian fiance he met on Grindr, who happens to be a professional dancer on Dancing With The Stars. The couple own two French Bulldogs and are planning a commitment ceremony at Cece’s house in the Hamptons in the summer of 2020, where Sam Smith is rumored to be performing and officiating.

THEN                                                                                                   NOW

Georgina Sparks

Georgina is the head of the PTA and Queen Bee of mean moms at her son, Milo’s, school. She has had more botox, fillers and plastic surgery than is medically advisable, but takes great pleasure in terrorizing her doctor, fellow parents and teachers on a regular basis, just for fun, because she can and because she’s kinda bored. In reality, she couldn’t care less about organic food, playdates or fundraisers. She has an on-again-off-again marriage with Jack Bass (they’ve divroced and gotten back together three times after numerous incidents with infidelity by both parties) and the couple are ‘trying’ for another baby, but Georgina was never a huge fan of children and had an IUD put in without Jack’s knowledge over six months ago. She is still loosely tangled up with the Russian mafia and often moonlights as a spy and helps them with undercover missions, mainly because having a secret life makes things a bit more interesting.

Vanessa Abrams

THEN                                                                                                   NOW 

To be honest, I considered leaving this one out entirely because who even likes Vanessa, right? But without giving it too much thought, I imagine Vanessa definitely had a much-needed glow up in the past few years and is now an English teacher at a primary school in Guadalajara. She spends so much time around children, that she decides she doesn’t really need her own right now, but is enjoying dating up a storm on PlentyOfFish (the only app she’d consider using, because from a political standpoint, she likes that the power is in the hands of the women). She spends her spare time doing yoga, taking pictures of vegan and gluten-free Mexican food for Instagram and walking the stray Chihuahua she resqcued and named Tamale. She is still an activist and protests against anything and everything under the sun.

THEN                                                                                                   NOW


I mean, let’s face it. Dorota was a legend. She knew how to operate surveillance equipment, file restraining orders, spy on the enemy, throw a kickass party and decorate rooms and offices to the very high standards of fashion girl on the Upper East Side. Which is why, after many years of devoted service, Blair decides to thank her by setting her up with her own business, which could be almost anything given how multi-talented she was. But I’m leaning towards thinking it was either an interior decor company, a party planning business or something along the lines of a finishing school / training academy for wannabe Manhattan house help from various parts of the world to help them achieve a high standard of service and be as multi-talented as she was, so they could procure the best jobs in the city. She does all of this, of course, whilst still Married to Vanya and busy with their little ones, Ana and Leo.

PS Remember Willa Weinstein? The girl who made the ‘art cinema’ video who went to NYU with Blair, Vanessa and Dan would now be pitied, ridiculed or even socially excommunicated from the Upper East Side due to all the sexual allegations made against her father, Harvey Weinstein, in the past year.

And there you have it – my take on the Upper East Side crew if the show were still running in 2018. Where do you think your favourite characters would be now? Share your thoughts with me in the comments below or via social media – I’m @MascaraEverSat on Twitter or @MascaraEverySaturday on Instagram. See you at the next post! xx


Disclaimer: Fairly current cast images have been used to denote character transformations. All of the theories about the show and characters are purely fan-fiction. All images have been credited to their sources.



  1. February 1, 2018 / 11:30 am

    I don’t think the cast has changed. Just the technology and fashion would be different 😜

  2. February 8, 2019 / 9:48 am

    One more episode of the gossip girl will be great. One showing what happens next will be great. This episode gets people hooked, not expecting what’s going to happen next which is brilliant. Also keep the good work.

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Anushka Moore is an almost-thirty-something blogger who moved across the world when the love she met on Tinder put a ring on it. She now lives in Manchester with her husband and her two little Poodle-cross fur children.

Her day job includes running her own social media content company and is the founder of popular Instagram account, Midsize Collective.

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