Can you imagine: Lili, Cole, Milo and Bentley?
Because I can and the more I think about it the more my heart is aching from cuteness of it.
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Can you imagine: Lili, Cole, Milo and Bentley?
Because I can and the more I think about it the more my heart is aching from cuteness of it.
Things took an insane turn while Milo was busy recording his latest podcast episode. Right in the middle of the interview, his guest reached their absolute limit, abruptly got up, said "this is ridiculous," and walked right out of the studio while the microphone was still completely live.
Milo was left utterly stunned, just sitting there in total confusion for a second before finally muttering, "okay... that's a first". Behind the scenes, the studio crew went into an absolute frenzy, with people scrambling and chairs loudly moving around as the interview went up in flames.
Yikes. It looks like someone didn't want to play by your script, Milo. We all know you love to talk, but it seems your latest guest preferred to let their feet do the talking instead. Let's see if that dramatic exit makes the final edit, or if you'll be left scrambling to fill the dead air.
The Sighting... 5:30 PM inside a recording studio.
The Drama... A podcast guest abruptly walks out mid-interview after calling it ridiculous.
The Fallout... Milo left stunned while the studio crew frantically scrambles.
xoxo, Gossip Girl 💋
@itsmilorutherford
Spotted: Milo, currently serving as a one-man wrecking ball for the moral compasses of the Upper East Side.
They say standards are what keep us civilized, but apparently, three seconds of eye contact with Milo is enough to turn even the most refined socialite into a total amateur. It’s the ultimate power move—not even saying a word, just looking your way and watching your entire personality dissolve like a sugar cube in a hot latte.
It’s pathetic, really. But also, let’s be honest: in a town full of people trying so hard to be noticed, there’s something terrifyingly effective about a boy who makes you forget who you are just by noticing you back. Standards are easy to have when nobody is testing them, but Milo seems to be the ultimate final exam—and most of you are failing beautifully.
Try to keep your composure, Anonymous. If you start sweating every time a handsome boy looks your way, you’re going to ruin that expensive silk blouse before the first course is even served.
You know you love me.
XOXO, Gossip Girl
@itsmilorutherford
In a world where everyone is trying to stand out, there’s something undeniably powerful about two people who actually manage to look like they belong together. It’s the ultimate aesthetic flex—a match that’s so photogenic it almost feels scripted. But let’s be real, darlings: looking "good together" is the easy part. The real test is what happens when the cameras are off and the filters are gone.
Is this a budding new power couple or just a very well-lit coincidence? Either way, I’m keeping a close eye on this duo. After all, the prettiest pairs usually have the most interesting stories to hide.
You know you love me.
XOXO, Gossip Girl
@dylanrjackson @itsmilorutherford
It seems Milo Rutherford’s invitation wasn’t the problem, but his wardrobe choice definitely was. While he was yelling about being on the list, the real crime was showing up to a grand event looking like he was headed to a casual Sunday brunch. In a room full of couture and black-tie standards, Milo’s super casual ensemble was a bigger red flag to security than a fake ID.
Security might have mistaken him for a crasher, but the fashion police have already issued a warrant for his arrest. It’s one thing to have the right name, but in this town, you have to have the right look to match the venue. Milo might be inside the Green with Envy party now, but looking that underdressed amongst the elite is its own kind of social suicide.
If Emir Atlan hadn’t stepped in to vouch for him, Milo would have been tossed to the curb for the simple sin of a bad outfit. Next time, Milo, try checking the dress code before you check your ego at the door. Being invited is only half the battle; actually looking like you belong there is the part you clearly missed.
The Faux Pas... super casual outfit.
The Confusion... security thought he snuck in.
The Bailout... Emir Atlan.
xoxo, Gossip Girl 💋
@itsmilorutherford
The notification chimes across the Upper East Side...
Manhattan's nights are always glamorous, but the Green with Envy bash at the Waldorf Astoria is taking things to a whole new level – and honey, the fashion is already more layered than a Blair Waldorf scheme! We've dimmed the lights, filled every glass with something sparkling, and thrown open the doors to everyone brave enough to dress for the occasion. From emerald gowns to forest green fits, people aren't just here to mingle – they're here to make sure we remember exactly who they are…
Let's be real – while most folks are busy trying to look effortlessly chic, your favorite informant is busy taking notes. Every corner you turn there's a new look to dissect – some are serving old money elegance, others are going all out with drama and daring, and a few… well, let's just say they might've confused "Green with Envy" with "green with poor judgment." But that's what makes tonight so delicious – one dress code, thirteen very different universes, and I have opinions…
Alright, enough pleasantries – let's get down to what you really came here for. Here's who's owning the Waldorf and who should've stayed in their universe…
XADEN RIORSON - A Wingleader who commands dragons and shadow magic showing up to the Waldorf Astoria in an oversized forest green tee, a beanie with a smiley face on it, and black joggers. The pearl necklace and Hublot watch are doing their absolute best to save him – and honestly? They're working harder than they should have to. The color is right, the brooding energy is effortlessly there, but darling – this is the Waldorf Astoria, not the Basgiath War College training grounds. We know you're used to dodging death, not dress codes, but still. He's serving "too dangerous to care" energy, which would be devastatingly charming if caring was optional tonight. It is not. Rating: 6/10 🐉@itsxadenriorson
MILO RUTHERFURD - A mint long-sleeve and grey sweatpants. Sweatpants. With a cigar and aviators, no less, like he's auditioning for a role nobody cast him in. He wandered into a Green with Envy gala at the Waldorf Astoria looking like he just rolled off a golf course in Malibu and took a very wrong turn somewhere on Fifth Avenue. The color is technically correct – we'll give him that much, and only that much. Everything else is a misdemeanor. He's serving "I did not read the invitation" energy, which is frankly the only explanation we're accepting tonight. Security, a gentle word please. Rating: 3/10 🚨@itsmilorutherford
BARRY CIRILLO - Now here's our OBX Pogue who clearly took the very scenic route to Manhattan – possibly via a theatrical production somewhere off Broadway, given the face paint situation on his cheek. That rumpled slate suit, open collar, and hair pulled loosely back should not work as well as it does, and yet somehow here we are. There's something about the brooding indifference, the lived-in elegance, the complete and total unbothered energy that makes him look like he was always meant to be perched exactly there. A Pogue at the Waldorf Astoria is not something we expected to be writing about tonight, but Manhattan is full of surprises. He's serving "I crashed this party and I'm somehow the most interesting person in it" energy – and the green decor surrounding him is doing the heavy lifting on the theme front. We'll allow it. Rating: 7/10 🌊 @itsbarrycirillo
BLAIR WALDORF-BASS - Finally. The Upper East Side's reigning queen arrived in a floor-length black and green floral gown, a delicate gold necklace, and a structured black clutch – and reminded every single person in this room what it truly means to dress for an occasion. The green florals against the black lace are nothing short of exquisite, the auburn hair is immaculate, and the overall effect is someone who didn't just understand the assignment – she wrote it, rewrote it, and had it monogrammed. She's serving "I was born for rooms exactly like this" energy, because she absolutely was. Rating: 9.5/10 👑@xoxoblairwb
WAVERLY BRODER - Oh, to arrive draped in sage and gold like mythology made flesh. That one-shoulder goddess gown with its trailing satin panel, gold embellishment, and daring thigh slit is giving ancient royalty meets modern red carpet – and she is completely, utterly eating it. She came here to be photographed, to be talked about, to be envied – and every single inch of that gown is delivering magnificently on that promise. She's serving "I am the event and the event knows it" energy, and tonight darling, she just might be right. Rating: 9/10 ✨@xoxowaverlyb
KATHERINE PIERCE - Centuries of surviving, scheming, and reinventing herself, and she still walks into a room like she invented the concept of an entrance. That sage satin draped cowl neck gown with its elegant thigh slit and barely-there heels is clean, timeless, and absolutely lethal – much like its wearer. She will walk out of here having stolen someone's heart, their boyfriend, and possibly their immortal soul, and she will look completely flawless doing every single bit of it. The simplicity IS the statement, and after five hundred years she knows that better than anyone alive – or otherwise. She's serving "I don't need to try and that's precisely what makes it terrifying" energy. Rating: 8.5/10 🖤 @xoxokatherinep
BRITTANY ANDRAS - Forest green, long-sleeved, sculptural ruching, floor-length perfection, with those barely-visible cage heels peeking out like a very elegant secret. This gown does not ask for your attention – it commands it, quietly and completely. The twisted draping is architectural, the fit is nothing short of devastating, and the overall effect is someone who came to this event specifically to make everyone else feel underdressed by comparison. She IS the gala. She IS the aesthetic. She IS what the invitation should have looked like when it arrived on your doorstep. Rating: 10/10 💚 @xoxobrittanya
EMIR ATLAN - Full green monochromatic commitment – linen shirt open over a white mesh tank, textured green trousers, jewelry, man bun, with the city lights behind him doing their absolute best to keep up. The color dedication alone is noted and deeply respected. The mesh tank underneath is giving Mediterranean summer vacation in the most effortlessly attractive way possible. The white sneakers at the Waldorf Astoria, however, are giving… a conversation we really do need to have at some point this evening. He's serving "I'm handsome enough to get away with this and I know it" energy – and he is, which he absolutely knows, which is half the problem. Rating: 7/10 😏 @xoxoemiratlan
BELLE MONTROSE - She burst through those Waldorf doors in a neon lime ruffled one-shoulder mini dress like a firework that did not ask for anyone's permission, and honestly? Good for her. The ruffles are maximalist and magnificent, the color is aggressively joyful, and she is having the absolute time of her life – and in a room full of people trying very hard to look like they're not trying, that kind of unbridled enthusiasm is its own very specific kind of chic. She's serving "I dressed for fun and fun had the audacity to show up" energy, and we respect the commitment entirely. Rating: 7.5/10 💛 @bellexmontrose
ROBIN BUCKLEY - She floated through those Waldorf doors in a sheer mint column gown and every single conversation in the room paused mid-sentence to watch. The gossamer fabric, the ethereal draping, the quiet confidence of wearing something this breathtakingly daring without a single apology or backward glance – it is hauntingly beautiful and entirely unforgettable. She's serving "Pre-Raphaelite painting that somehow received a Waldorf Astoria invitation and deserved it more than anyone" energy, and we are completely, utterly here for every translucent inch of it. Rating: 9/10 🌿 @rockinxrobin
MARILYN SINCLAIR - Sage green jewel-trimmed shift dress, silver stilettos, hair elegantly pinned up. Mod. Sharp. Precise. Those crystal embellishments running along the seams are doing exactly what they were put on this earth to do, and those silver heels are the perfect punctuation mark on an already completely impeccable sentence. She looks like she was dressed by a very chic time traveler who knew exactly what this particular party needed and delivered accordingly. She's serving "understated is the new over the top and I knew it first" energy – and she is not wrong. Rating: 8.5/10 💎@themarilynsinclair
BRIAR COLEMAN - Green velvet crop top, micro skirt, polka dot platform heels, floral earrings, black headband. She walked in like a statement and sat down like tomorrow's headline. The velvet is sumptuous and rich, the color is everything the theme asked for and then some, and those shoes are wonderfully, gloriously, magnificently unhinged in the most deliberately intentional way imaginable. She does not care what you think, and that complete and total self-assurance is precisely and exactly why it works as well as it does. She's serving "I make the rules and then I break them better than you could ever follow them" energy. Rating: 9/10 💚 @thebriarcoleman
KIARA CARRERA - A Pogue from the Outer Banks standing in the Waldorf Astoria in a mint ribbed cut-out maxi dress and white platform sandals, looking like she belongs here more than half the Upper East Siders who were quite literally born to. The cut-out detail is modern and supremely confident, the ribbed fabric is sleek and quietly architectural, and she carries the whole thing like the Waldorf Astoria is just another perfectly ordinary Tuesday evening. The platforms are a touch casual for the occasion, but when you look this effortlessly good darling, the shoes become a very charming footnote. She's serving "I came from the wrong side of the island and I'm still the best dressed person in this room" energy. John B who? Rating: 8/10 🌊 @thekiaracarrera
And there you have it, Upper East Siders – and our very special guests from realms, universes, and barrier islands far beyond Manhattan. Brittany Andras remains completely and utterly untouchable. Blair remembered she was born for rooms exactly like this one. Katherine Pierce has been the best dressed woman in any room for five centuries and tonight is no exception. And somewhere out there, Milo Rutherfurd is still wearing those sweatpants.
The Waldorf Astoria has seen many remarkable things in its long and storied history. It has never seen quite this.
You know you love me.
XOXO, Gossip Girl 💋
In a city where everyone is desperately trying to be noticed, Milo is making waves by doing the exact opposite. There’s a fine line between being "cold" and simply being indifferent, and according to the latest whispers, Milo isn't just chilly—he simply doesn't care about any of you.
While the rest of the Upper East Side spends their energy social climbing and seeking approval, Milo’s total lack of interest is the ultimate power play. There is nothing more frustrating to a room full of people who think they’re important than someone who doesn't even bother to acknowledge their existence. It’s not malice; it’s just a complete lack of investment in the local drama. It seems if you're waiting for a reaction from him, you might be waiting a very long time.
You know you love me.
XOXO, Gossip Girl
@itsmilorutherford
SPOTTED: Milo Rutherford and Briar Coleman giving us a masterclass in "High-Low" Manhattan living. While Briar usually saves her arguments for the courtroom and Milo saves his for the airwaves, it looks like they’ve finally found some common ground—likely somewhere between a designer sample sale and a 4:00 AM diner run. Milo is serving his signature "comfy-cozy but make it a tax bracket" look in that oversized fleece, while Briar proves that even in a hoodie and thigh-high boots, she’s still the most intimidating person in the room.
Rumor has it that this wasn't just a casual morning stroll. Word at the courthouse is that Briar has been pulling late nights, and it’s not just to prep for her next big trial. Is our favorite legal eagle helping Milo navigate a particularly nasty libel suit, or is she just trying to convince him that his podcast listeners don’t need to know everything about her private life? In this town, when a shark meets a shock-jock, the only thing guaranteed is that someone is going to end up being the lead story.
Despite their very different day jobs, these two seem to be perfectly in sync or at least perfectly comfortable in each other's oversized laundry. Milo’s been unusually quiet on his latest stream about his personal life, but this photo says everything his NDAs won't let him. Is Briar the secret muse behind his latest episode or is Milo just the chaotic distraction she needs to unwind after a day of dealing with the Upper East Side’s most litigious families?
Whether they’re heading to a recording studio or a secret breakfast spot to hide from the paparazzi, one thing is certain: this duo is the most unexpected crossover event of the season. A lawyer who knows where the bodies are buried and a podcaster who wants to dig them up? Watch your step, you two; the higher the pony, the harder the fall.
You know you love me.
XOXO, Gossip Girl
@thebriarcoleman @itsmilorutherford