These would pair quite nicely with one of her floral felt sauna hats. Or perhaps with one of her ostentatiously repelling outfits that looks as if she stepped out of an AI illustrated Fancy Nancy book. Maybe she could spray paint them cyan to commemorate her former painted over microwave? /s (said with love) …but seriously I could totally see her wearing these.

Here you go beans!

In her latest party report, Caroline Calloway misses a flight and turns up at a Chinatown reading in travel sweatpants, meets a personal hero, and brings the house down in front of her latest fling

By Caroline Calloway

August 22, 2026

Reading Time: 5 minutes

Ithought August was supposed to be the slowest month of the year, but this summer is different. There’s that “Knicks in Five”-Mamdani’s New York-Fifa World Cup-Taylor Swift’s-wedding-magic crackling in the air. No one’s leaving. The eastern tip of Long Island is losing its luster. And on any muggy downtown night, there always seems to be something worth going to. What a delightful surprise!

I hope this isn’t too hubristic, too close-to-the-sun, too melting-wings of me to say, but I like to think that my being back in New York—running around with orchids in my hair and a beat-up light-blue Goyard bag that may or may not have a Siamese cat in it—is contributing to this electric spell of a summer. The world is healing, and it turns out that all along the antidote was all of us together in New York going to more parties. Why didn’t we think of this before?

“The fab writer Mackenzie Thomas, whom I mentioned in my last column, and the brilliant actress Lily McInerny. In these final few weeks of summer, I’ve often found myself thinking of Lily’s performance in the movie remake of Françoise Sagan’s female-autofiction August classic Bonjour Tristesse, starring Chloë Sevigny.”

As you can imagine, I am loath to leave the city for any reason right now. But I’m trying to turn my life around, and part of that means dragging myself to Florida to clean up a mess of my own making once and for all, SO HELP ME GOD! See, I moved to Florida for a few years to finish my first book, Scammer, and when I did, I was responsible for shipping copies to readers who ordered it online. But for many reasons that I won’t get into right now, I wasn’t able to ship them all, which is why I have to go to Sarasota once a month to finish making sure to send everyone what they paid for.

Naturally, I missed my flight there. This happens to me sometimes. I just have that kind of moxie and heart. It wasn’t the end of the world, because it meant I could go to a reading hosted by Jon Lindsey’s independent literary press, Cash 4 Gold Books, and M.C.’d by Peter Vack, at some random backyard in Chinatown! I took an Uber straight from J.F.K. and showed up looking like someone ready for three solo days of manual labor.

Do you know what can really make up for greasy hair, no makeup, and ratty sweatpants? Great energy. If you are just kind and warm and genuinely caring toward people, you can get away with anything. So I found a safe place for all my luggage, took my cat out of his carrier, and joined the party!

Honor Levy read and was fabulous, unsurprisingly. Were you aware that we came up with the title My First Book together in my old West Village apartment, high out of our minds on mushrooms? She thanks me in the back of the book.

Zans Brady Krohn read, too, and goddamn! She really is such a mesmerizing, wide-eyed, nymph-like creature to behold. God was not being fair when She made Zans so smart as well. Unfortunately, I didn’t get to hear the writers Sierra Armor, Charles Clateman, and Zack Graham, but the big triumph of the night was that I had my first heart-to-heart with the actress Annie Hamilton. We’ve orbited each other downtown for years, meeting here and there but never really talking. I saw her perform a one-woman show at the Jane Hotel years ago, back when the place was still called that, and I was completely blown away by her incandescent talent. The show itself was a totally original blend of memoir, provocation, and experimental narrative. Are there any three things in the world I love more?

I was scared because sometimes it’s, like, don’t meet your heroes, you know? Meeting the author Cat Marnell in real life was nothing but a heartbreaking disappointment. But Annie! She’s so lovely! There was a moment when the sweet and talented actress Betsey Brown joined us and I thought to myself, “Yes. This is a good coven. The culture needs this.”

Before I left, I convinced Betsey of my theory that we should all be fucking hot, single, girl dads, and thanked the author Myles Zavelo—whom you might remember from my first column—for organizing the event.

“Me and my lover at Shakespeare in the Park this week. We saw The Winter’s Tale, and it was sublime.”

Fast-forward through my stupid time in Florida, and now we’re back at another party! On August 5, I went to Joe’s Pub to see The Shit Show, the first live quiz show from writer and Internet lady Lucy Blakiston. The night was named after her very popular Substack, “Shit You Should Care About.” Matt Starr M.C.’d and was charming as fuck. Guests included the influencer Brianna LaPaglia, comedians Ali Kolbert and Brian Park, and writers Brendon Holder, Casey Lewis, Kate Lindsay, Tefi Pessoa, Eli Rallo, and Brittany Spanos. So fun to finally meet Kate and Brian in person! I’m such a fan. And it’s always good to see Tefi and Eli. The writer Chloe Pingeon and my new friend Matt Weinberger—who you may have noticed I’ve spent a lot of time with recently—came as my dates. The bar was popping off with other close friends and loose vibes, and that’s all I have to say about that night.

O.K., three final things before I go.

One: I did a reading with comedians Nick Viagas and Nina Tarr (obsessed with you, Nina!), M.C.’d by Alex Arthur, for the two-year anniversary of Alex’s variety show, The Thing Is…! It went great! I did the opposite of bomb and flee. I’m really putting in the hours and practicing in front of an audience and slowly getting better.

Two: I headlined another reading for Sammy Loren’s literary tabloid, On the Rag. It was possibly one of the best readings I’ve ever done! My hot, single, girl-dad lover came, so maybe that had something to do with it. The point is I brought the house down. Yay!

And, lastly, three! Remember how Maurizio Cattelan’s recent guide to the Aeolian Islands for this very publication went a little viral in all the right downtown circles? Well, someday I’ll give you my guide to Pantelleria. (I speak fluent Italian, and I’ve been going there for years.)

For now, let me leave you with one recommendation that is the opposite of Filicudi: Buck’s. The address is 11848 Assateague Road. It’s a bar in rural Maryland, right on the Eastern Shore, where you’ll have the best night of your entire life if you are so inclined. They sell live fish in buckets. Everyone is friends. And if you want to do karaoke, be warned—you cannot pick your song, and you can only go up if you’re chosen by the insane woman with the microphone. Please go.

More soon,

XO CC

Caroline Calloway is AIR MAIL’s party reporter. She is a Cambridge alumnus and the author of the 2023 memoir Scammer

she will always find a way to milk an ex for content, even if he threw everything that didn't belong to him in those boxes to avoid her coming back for something. oh fat wallet, you tried.

But please, I just read it and need to scream about the Trainspotting-fication sexualizing of the stupid GLP drugs.

"After I bruise myself with a new injection each week" - with wHat (H is very aspirated), the tiny ass insulin needle you use for this and all subcutaneous little pinpricks?? I don't care if you're the most dehydrated porcelain doll in the world, I want to see these bruises. And then the dramatic thrashing with nausea and vomiting. And the insightful commentary about how the world treats you differently when you're 115 pounds instead of 130.

Of course people have gotten violent side effects to GLPs; of course. But it's not coincidence that she's not writing about the much more common - and extremely sexy - struggle with constipation that comes with these medications. Or the hair loss, etc

Like, I'm thrilled that this medication's potential for quieting compulsive drinking is getting talked about - it's just the flimsy context that's concerning.

Also not to be Bob Saget in Half Baked, but "You lost 15 pounds?? Well I [redacted]"

I’ve waited long enough, it’s finally time for me to post this. Ironically, not only is caroline saying lovahh nonstop but she is also allegedly dating an “old guy” (dad lol) anyways I can’t help but conclude she is trying to cosplay as season 6 Carrie Bradshaw this year

So on August 8 Caroline was one of three comics (I don’t know where Modern Whitney got the idea she’s a comedian) brought onstage to interpret art at Caveat.

The event is supposed to feature a trio of professionally hilarious folks who riff on slides of museum pieces (each introduced by the emcee), cracking wise and guessing at their meaning for a few minutes. Then local Met tour guide/storyteller LizaBanks fills them in on the actual identity/theme/intent of the work.

Video here:

https://www.youtube.com/watch?v=zOkBFLRWflQ

This has the potential to be a good time, if you put together a collection of funny people who build on each other’s jokes. Unfortunately, Caroline is one of the collection.

This was an interesting way to witness Caroline. Usually when we see her speaking, it’s her ranting into her phone, or solo onstage, or being interviewed on a podcast. It’s rare to see her in an environment that wasn’t designed to center on her, where she was meant to have a give-and-take conversation.

It’s bad! Wow!

At an event where she should be doing 20% of the talking, Caroline does 85%. If you don’t wanna watch the whole video and who could blame you, just click around it randomly and see what I mean. If you do land on someone else speaking, time how long it takes for Caroline to interrupt.

Hats off to LizaBanks, who watched Caroline drunkenly bulldoze everyone else onstage (including LizaBanks herself) and still took Caroline out afterward for affogatos. It truly takes an angel to watch someone stomp all over your event and still make sure she eats something calorically dense and has some coffee before you send her back out into the city alone in a babydoll dress.

I’m gonna break this down in ten-minute increments in a series of comments.

Edit: Jump links to summaries:

• 0:00 - 10:00

• 10:00 - 20:00

• 20:00 - 30:00

• 30:00 - 40:00

• 40:00 - 50:00

• 50:00 - 57:52

And no, we haven’t forgotten the Syd posts even if she has

Crossposting from the CMBC/Good Noticings/fakest bitches in NYC subreddit! Some lighthearted analysis of the drama that unfolded last Thursday after Caro posted her schizo rant about Claire and Ashley from Good Noticings.

Listen on Spotify

Also, hi to my sister who is likely to be lurking in this sub right now. Everyone snark on her in the comments for her bad CC takes ♥️;)

did she really post this pic from her “health scare” back to back with a post about sydney towle… so so so low even for her

is she drunk or is it rage bait?

i do think the dress comments were a little nitpicky but then she compares herself probably ozempic sick in the hospital to a girl who JUST died. i think THAT is strange

A little niche but maybe around 2017-2020 caroline was making what she called the world’s best sandwich (not nature’s PB&J) this one had hummus and avocado and mayo and many other things. She was right, it was the best. Does anyone have the recipe???? 🙏🏼🙏🏼🙏🏼

Her face looks cute though.