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Gossip Girl: This Is What Your Favourite Upper East Siders Look Like Now

Grazia logo Grazia 18/09/2020 Katie Rosseinsky
Leighton Meester, Penn Badgley, Blake Lively, Taylor Momsen, Chace Crawford, Ed Westwick posing for a photo: Gossip Girl cast © Credits: Getty Gossip Girl cast

It's been over eight years (yes, really) since we said goodbye to our favourite Upper East Siders, and we're still seriously missing our weekly insights into the scandalous lives of Manhattan's fictional elite, which is why we were so excited to here that our favourite stateside teen drama was getting a reboot. Hooray!

The new show, which will stream on HBO Max and feature 10 hour-long episodes, is set to introduce us to a new generation of Upper East Siders and show how social media has changed the landscape of NYC since the days of bloggers ruling the city.

To fill the void until the new show comes out, we've channelled Gossip Girl herself (or should that be himself?) and done some digging into what Serena, Blair and co. are up to now. You know you love us, XOXO...

Serena van der Woodsen

Michele Lister et al. standing next to a person: Gossip Girl Then and Now © Provided by Grazia Gossip Girl Then and Now

Blake Lively starred the the UES's ultimate effortless cool girl, Serena van der Woodsen.

Blake Lively

Blake Lively et al. standing in front of a crowd posing for the camera: Gossip Girl Then and Now © Credits: Getty Gossip Girl Then and Now

As one half of the world's most photogenic couple (with Ryan Reynolds) and the original instigator of the phrase 'hair goals' (probably), Blake Lively needs no re-introduction. Since starring as Serena van der Woodsen, Blake has starred in The Age of Adaline, launched an ill-fated, 'Goop'-esque lifestyle site Preserve and welcomed three young daughters. Most recently, she starred in shark horror flick The Shallows and put us off surfing forever.

Leighton Meester, Penn Badgley, Blake Lively, Taylor Momsen, Chace Crawford, Ed Westwick posing for the camera © Getty

Blair Waldorf

Leighton Meester looking at the camera: Gossip Girl Then and Now © Provided by Grazia Gossip Girl Then and Now

Leighton Meester was Blair Waldorf, the queen of the Upper East Side.

Leighton Meester

Leighton Meester posing for the camera: Gossip Girl Then and Now © Credits: Getty Gossip Girl Then and Now

Now that she's no longer playing the Upper East Side's premier ice queen, multi-talented Leighton has taken time to work on her music career, and released her debut LP, Heartstrings, in 2014. Her Broadway debut came in 2014, when she starred in the highly acclaimed adaptation of John Steinbeck's Of Mice and Men, opposite James Franco and Chris O'Dowd. She started dating The OC star Adam Brody in 2013, meaning that in the ultimate teen drama crossover, Blair Waldorf and Seth Cohen are now a real life item. The couple married in 2014 and have one daughter together.

Chuck Bass

Ed Westwick wearing a suit and tie: Gossip Girl Then and Now © Provided by Grazia Gossip Girl Then and Now

Brit actor Ed Westwick starred as charming, but slightly evil, bad boy, Chuck Bass

Ed Westwick

Ed Westwick wearing a suit and tie is standing in the snow: Gossip Girl Then and Now © Credits: Getty Gossip Girl Then and Now

Ed has starred opposite future Oscar nominee Felicity Jones in underrated 'snowmantic comedy' Chalet Girl. He dabbled in Shakespeare as Tybalt in the 2013 film adaptation of Romeo and Juliet (alongside Douglas Booth and Hailee Steinfeld), and most recently starred as a serial killer in short-lived US crime drama series Wicked City. Ed reportedy auditioned to play Han Solo in the much-anticipated Star Wars spin-off feature, but faced competition from the likes of Taron Egerton, Dave Franco and Alden Ehrenreich. He's also been seen in thrillers Jekyll Island and Take Down.

Dan Humphrey

Penn Badgley wearing a suit and tie: Gossip Girl Then and Now © Provided by Grazia Gossip Girl Then and Now

Really, what is there to say about Lonely Boy?

Penn Badgley

Penn Badgley wearing a suit and tie: Gossip Girl Then and Now © Credits: Getty Gossip Girl Then and Now

Dan Humphrey has carved a niche as the ultimate hipster, and is regularly spotted around Brooklyn rocking a beard of varying lengths. After splitting up with on-screen and real life girlfriend Blake Lively, Penn went on to date actress and musician Zoe Kravitz from 2011 to 2013. These days, when he's not picking holes in that huge Gossip Girl reveal ('It doesn't make sense at all. It wouldn't have made sense for anybody,' he told People last year), he's making music with his band MOTHXR (note the edgy spelling) and playing everyone's favourite serial killer (yes, this is problematic), Joe, on Netflix's You.

Nate Archibald

Chace Crawford wearing a suit and tie: Gossip Girl Then and Now © Provided by Grazia Gossip Girl Then and Now

Chace Crawford was the Upper East Side's pretty boy, Nate Archibald.

Chace Crawford

Chace Crawford wearing a suit and tie: Gossip Girl Then and Now © Credits: Getty Gossip Girl Then and Now

Since graduating from Gossip Girl, Chace Crawford has starred in a handful of films, including 2012's What To Expect When You're Expecting and indie comedy Mountain Men. Most recently, he starred in short-lived soap opera Blood & Oil (which was billed as the new Dallas) and landed a role opposite Amber Heard in comedy What's The Point, written by Lake Bell. In a move worthy of Nate Archibald himself, Chace is currently reported to be dating his Blood & Oil co-star Rebecca Rittenhouse, but has also been linked to Vampire Diaries actress Nina Dobrev. We don't know what to believe any more.

Jenny Humphrey

Taylor Momsen standing on a sidewalk: Gossip Girl Then and Now © Provided by Grazia Gossip Girl Then and Now

Jenny Humphrey, AKA sweet-teen-turned-fashion-nightmare, was played by IRL rocker, Taylor Momsen.

Taylor Momsen

Taylor Momsen standing on a stage: Gossip Girl Then and Now © Credits: Getty Gossip Girl Then and Now

Taylor Momsen quit the show after just four seasons, with the aim of focusing on her music career. Her band The Pretty Reckless released their first single, the cheerily titled 'Makes Me Wanna Die,' in 2010, which was followed by a debut album, Light Me Up. The group supported everyone's favourite angsty opera-rock gang Evanescence on tour in 2011, and released follow up album Going To Hell in 2014. Pop trivia fans will be interested to learn that TPR's fourth single, 'Kill Me,' was the last song to feature in the final episode of Gossip Girl Well, it was either going to be that or Rufus' one hit wonder, 'Everytime'...

Lily van der Woodsen

Kelly Rutherford et al. on a sidewalk: Gossip Girl Then and Now © Provided by Grazia Gossip Girl Then and Now

Kelly Rutherford was Serena's mum, Lily.

Kelly Rutherford

Kelly Rutherford et al. standing in a room: Gossip Girl Then and Now © Credits: Getty Gossip Girl Then and Now

Since Gossip Girl came to an end, Kelly Rutherford has concentrated on small screen roles, with recurring parts in US legal drama Reckless and the critically acclaimed series Quantico. The actress was also embroiled in a long-running, globe-spanning custody battle over her son and daughter with her ex-husband, German businessman Daniel Giersch, which she eventually lost in December 2015.

Rufus Humphrey

Matthew Settle wearing a suit and tie: Gossip Girl Then and Now © Provided by Grazia Gossip Girl Then and Now

Rufus, dad to Dan and Jenny, was the ultimate on-screen dad crush.

Matthew Settle

Matthew Settle wearing a suit and tie: Gossip Girl Then and Now © Credits: Getty Gossip Girl Then and Now

Since hanging up Rufus Humphrey's leather jacket (and unplugging the waffle maker, probs), Matthew Settle has starred in a succession of intriguingly named films - Ouija, Marshall the Miracle Dog or A Sister's Nightmare, anyone? After the star posted a series of sweet photos of himself with on-screen on-off love interest Kelly Rutherford, Gossip Girl fans went into meltdown at the thought of an IRL romance - #LilyAndRufus even ended up trending on Twitter. In a mix up worthy of one of the show's plotlines, Matthew isn't actually dating Kelly - he has a daughter with his long-term girlfriend Maria Alfonsin. Kelly and Matthew have remained firm friends since their time on the show, and the actor publically lent his support during Kelly's difficult custody battle.

Vanessa Abrams

Jessica Szohr looking at the camera: Gossip Girl Then and Now © Provided by Grazia Gossip Girl Then and Now

Vanessa is probably the main reason you still can't cope with hipsters was on the show for a few season, before announcing that she'd be 'studying abroad' for a while.

Jessica Szohr

Jessica Szohr standing in front of a building: Gossip Girl Then and Now © Credits: Getty Gossip Girl Then and Now

Since leaving the Upper East Side behind, Jessica has had roles in films like The Internship and Ted 2, and most recently has starred in Kingdom, a TV drama about a family of MMA fighters (which, bizarrely, also stars Nick Jonas). She's also a long-time member of Taylor Swift's squad - her friendship CV boasts a cameo in the singer's '22' video and* an appearance in Tay's Fourth of July 'family portrait' Instagram from 2014 (seated next to Lena Dunham and model Jessica Stam, no less).

Dorota

Zuzanna Szadkowski posing for the camera: Gossip Girl Then and Now © Provided by Grazia Gossip Girl Then and Now

Dorota was the real MVP of Gossip Girl.

Zuzanna Szadkowski

Zuzanna Szadkowski holding a sign: Gossip Girl Then and Now © Credits: Getty Gossip Girl Then and Now

Zuzanna has since landed roles in TV dramas like Loserville, The Knick and The Good Wife, and even swapped the Upper East Side for (gasp!) Brooklyn with a recurring role in the fourth season of Lena Dunham's Girls. And while this is all well and good, we were happiest to learn that Zuzanna is still best of pals with Leighton Meester in real life - speaking to The Hollywood Reporter in 2015, Leighton's husband Adam Brody described the actress as 'one of my wife's best friends.' Blair and Dorota - the ultimate in squad goals?


Gallery: Gossip Girl then and now: see how much the cast has changed over the years (Hello!)

Georgina Sparks

Michelle Trachtenberg sitting at a table: Gossip Girl Then and Now © Provided by Grazia Gossip Girl Then and Now

Michelle Trachtenburg was New York's arch-manipulator, Georgina Sparks.

Michelle Trachtenburg

a person posing for the camera: Gossip Girl Then and Now © Credits: Getty Gossip Girl Then and Now

Michelle Trachtenberg has had a handful of TV appearances and according to her Twitter bio, is currently 'an actress/producer/writer/believer in Unicorns.' In a bizarre twist of fate, bringing together fictional New York teen royalty with actual British royalty, Michelle is apparently pals with Princess Eugenie. She was regularly photographed with the Princess after she moved to the US in 2013, and posted a picture to Instagram with '[her] girl E,' who showed her around a gallery in downtown LA. Even Gossip Girl herself couldn't have predicted this...

Eric van der Woodsen

Connor Paolo is Serena' little brother, Eric.

Connor Paolo

Connor Paolo standing posing for the camera: Gossip Girl Then and Now © Credits: Getty Gossip Girl Then and Now

Connor swapped Gossip Girl for the equally melodramatic Revenge in 2011, and played Declan in the first two seasons of the show. Since then, he's starred in horror flick Friend Request (think The Ring for the Facebook generation), an apocalyptic college drama called Like Lambs, and a TV show based on Nineties action-comedy Rush Hour. Oh, and he's still friends with Little J in real life - he starred in the video for The Pretty Reckless's single 'My Medicine,' and regularly attends their gigs to support his pal Taylor.

Tripp Vanderbilt

Aaron Tveit and woman posing for a picture: Gossip Girl Then and Now © Provided by Grazia Gossip Girl Then and Now

In case you forgot: Tripp wasn't exactly the most crucial character in the Gossip Girl canon, but he was Nate's equally photogenic cousin who ended up having an affair with Serena in season three.

Aaron Tveit

Aaron has arguably ended up as one of the show's low-key success stories. He gave a strong performance as student revolutionary Enjolras in the big screen adaptation of Les Miserables (opposite Eddie Redmayne and Hugh Jackman), and most recently starred as Danny Zuko in Fox's production of Grease! Live - add it to your Netflix watch list...

To tide you over until the reboot comes out, why not stream one of Netflix's best chick flicks?

He's Just Not That Into You

Netflix chick flicks © Provided by Grazia Netflix chick flicks

Stop making excuses for him, bottom line: he's just not that into you. If you don't want to hear it from us, let Jennifer Aniston tell you instead. A good one for that reality check we all need sometimes.

Grease

a group of people standing in front of a crowd: Netflix chick flicks © Provided by Grazia Netflix chick flicks

The OG chick flick, let Sandy's dramatic transformation and Danny's voluminous hair turn your night into the sing-a-long you didn't know you needed.

Easy A

a woman preparing food in a restaurant: Netflix chick flicks © Provided by Grazia Netflix chick flicks

Emma Stone at her best, Easy A shows what happens when rumours run wild — and what happens when you try to stop them.

Ghost

elaine johnson et al. wearing a hat: Netflix chick flicks © Provided by Grazia Netflix chick flicks

This film stars Demi Moore and Patrick Swayze as star-crossed lovers and Whoopi Goldberg as a psychic who tries to help them — do we need to say more?

Clueless

Alicia Silverstone et al. posing for the camera: Netflix chick flicks © Provided by Grazia Netflix chick flicks

If you need a reason to re-watch Clueless (as if!), do it for the fashion alone.

Always Be My Maybe

Ali Wong, Randall Park holding wine glasses: Netflix chick flicks © Provided by Grazia Netflix chick flicks

A Netflix original, Always Be My Maybe shows us what happens when childhood sweetheart reunite as adults. It also stars Keanu Reeves, so you should watch it for that reason alone.

I Feel Pretty

Amy Schumer et al. standing in a room: Netflix chick flicks © Provided by Grazia Netflix chick flicks

This silly-but-sweet flick shows how amazing life can be when you let go of all your insecurities and, well, feel pretty.

Legally Blonde

a woman walking down the street: Netflix chick flicks © Provided by Grazia Netflix chick flicks

It is a truth universally acknowledged that Reese Witherspoon's Elle Woods is an icon. Not only that, but Legally Blonde taught us some invaluable lessons. Shall we list them? Appearance is only skin deep, having legal smarts is cool and your ex is probably a moron who you're better off without. Oh and you can be a top legal hot-shot while wearing a lot of pink. What, like it's hard?

La La Land

a person throwing a frisbee in the air: Netflix chick flicks © Provided by Grazia Netflix chick flicks

Emma Stone and Ryan Gosling's Academy Award-winning musical is available to stream on Netflix and will definitely leave you desperate to book flights to LA.

Sixteen Candles

a man and a woman standing in front of a window: Netflix chick flicks © Provided by Grazia Netflix chick flicks

Molly Ringwald at her sweetest, we can remember watching this on our 16th birthday with our mum. A must-watch for anyone who's ever been 16 and felt like they didn't fit in.

Someone Great

Brittany Snow et al. posing for the camera: Netflix chick flicks © Provided by Grazia Netflix chick flicks

Jane The Virgin's Gina Rodriguez stars in this Netflix original is perfect for realising that sometimes, it's our girlfriends we need, not a man.

Two Weeks Notice

a group of people standing on a sidewalk: Netflix chick flicks © Provided by Grazia Netflix chick flicks

Hugh Grant at his best, this underrated romcom is definitely worth a watch (or a re-watch, as it always seemed to be on TV in the noughts...).

Think Like a Man

a man and a woman looking at the camera: Netflix chick flicks © Provided by Grazia Netflix chick flicks

Turns out the consequences of trying to get into your partners head can be pretty disastrous. Who would've guessed?!

To All The Boys I've Loved Before

a man standing on top of a grass covered field: Netflix chick flicks © Provided by Grazia Netflix chick flicks

Netflix's film adaptation of Jenny Han's young-adult novel is the perfect easy watch that will have you missing high school and feeling nostalgic for your first love.

You've Got Mail

a group of people sitting at a table in a restaurant: Netflix chick flicks © Provided by Grazia Netflix chick flicks

Why do all the best romcoms feature quaint bookshops? We don't know, but we don't hate it.

What To Expect When You're Expecting

Netflix chick flicks © Provided by Grazia Netflix chick flicks

Everyone's pregnant, well Cameron Diaz, Jennifer Lopez, Elizabeth Banks, Brooklyn Decker and Anna Kendrick are, and everyone is on some level is scared for what's to come. Don't worry, there are a lot of laughs along the way, too.

Trainwreck

Amy Schumer, Claudia O'Doherty sitting posing for the camera: Netflix chick flicks © Provided by Grazia Netflix chick flicks

Amy Schumer at her best, this film is perfect for when you feel like your life is falling apart and you need to know you're not alone.

When Harry Met Sally

a couple of people that are talking to each other: Netflix chick flicks © Provided by Grazia Netflix chick flicks

A classic for a reason, this movie is a must-watch for everyone.

Sex And The City: The Movie

a group of people posing for the camera: Netflix chick flicks © Provided by Grazia Netflix chick flicks

In the film version of what is arguably the greatest chick flick series of all time, Mr Big is stilling causing drama, all these years on. All the usual gang - plus Jennifer Hudson.

P.S. I Love You

Gerard Butler wearing a hat: Netflix chick flicks © Provided by Grazia Netflix chick flicks

Sometimes you just need a good cry, and Hilary Swank and Gerard Butler are here to help you with that.

Mama Mia! Here We Go Again

Pierce Brosnan et al. posing for the camera: Netflix Chick Flicks © Provided by Grazia Netflix Chick Flicks

The sequel to Mama Mia, the ABBA musical-turned-film sees Amanda Seyfried's Sophie reunited with her three dads, Diane from The Good Wife and Mrs Weasley from Harry Potter... but where's Meryl Streep?

Eat, Pray, Love

a person sitting in a park: Best Netflix Chick Flicks © Provided by Grazia Best Netflix Chick Flicks

Based on Elizabeth Gilbert's best-selling book of the same name, follow Liz she travels the world following her divorce, searching for good food, spirituality and love.

The Notebook

a man and a woman sitting in a field: Best Netflix Chick Flicks © Provided by Grazia Best Netflix Chick Flicks

What do you mean you haven't seen it? Settle in for a big weep with this adaptation of Nicholas Sparks' best-selling novel, set in 1940s America and staring Rachel McAdams and a delightfully waterlogged Ryan Gosling.

Amélie

a close up of Audrey Tautou: Netflix Chick Flicks Amélie © Provided by Grazia Netflix Chick Flicks Amélie

The film that launched Audrey Tautou's career and spawned a bazillion DIY fringe cuts is a quintessential chick flick insofar as (some) men seem to find it twee and irritating, while (many) women find it charming and quirky. And if you've never watched Tautou's titular Amélie on her quest to bring more joy into the world, it's definitely worth a watch with that aforementioned glass of red wine - if just for the tres beau shots of Paris.

READ MORE: Gossip Girl Is Getting A Reboot So Here's 45 Things You Didn't Know About The Original Cast

READ MORE: The Best Gossip Girl Outfits: A Look Back At The Upper East Sider's Fashion Formulas

WATCH: Blake Lively's suited and booted style

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