Art Daddy Exclusive: Larry Gagosian Is 80 and Still Dating Women Who Don’t Remember Blockbuster Video

Why is the art world’s most powerful man still swiping right on women who think Cindy Sherman is a TikTok trend?

Let me set the record straight. I have not been obsessing over Larry Gagosian since the dawn of the Young British Artists. I’m not some art ghost haunting auction houses or lurking in gallery shadows. This is fresh. This is hot off the press. My fascination with Lare Bear and being his next headline started just over a year ago. And trust me, it’s burning brighter than a Jeff Koons balloon dog at a Sotheby’s preview.

Larry Gagosian, the mega-gallery industrialist, billionaire art daddy, and man whose contact list probably weighs more than your student loans, is now 80 years old. Despite never marrying or having kids, he has a habit of dating women who could be his grandkids. Larry treats romance like a seasonal exhibition—quick, flashy, and designed to make you wonder what you missed while you were busy scrolling.

His recent dating history reads like a casting call for a Sofia Coppola period piece filled with pouty Prada faces and major parental issues. It’s always a May-to-December situation, but honey, we are deep into December now. Like the kind of December where you light a candle and put on Michael Bublé to soften the blow.

The most infamous name on this list is Anna Weyant. She’s the doe-eyed Canadian painter whose art looks like sad girl school with a twist of classical training. Somehow, she landed a spot in Larry’s mega-gallery, snagged solo shows at Frieze and TEFAF New York this year, and basically mastered the dark art of surviving the art world while still in her Saturn return. Seriously, Anna must have Larry’s birth chart, his email password, and probably a photo of him eating a banana at Art Basel to pull off that kind of power move.

Larry, Anna and Jeffery at an event.

When Larry and Anna split in 2024, I decided to make my move. I was brave. I was unhinged. I sent emails—plural. I wrote heartfelt Art Daddy dispatches. I even bribed a few PR girls with coffee and vague promises of exposure. Larry stayed silent. Not ghosting, more like a billionaire’s version of “I’m busy and you’re not a priority.” The silence was so respectful it felt like a Tom Ford suit pressed to perfection.

Larry and Anna during happier times.

Then, like a Moncler-clad virus, Erica Pelosini arrived. The Italian heiress-influencer-model-stylist-whatever who came to steal my man and possibly his soul. She looks like Anna if Anna only had brand deals and a Gucci chihuahua. Suddenly, she was everywhere with Larry, clinging to his arm at the Oscars like she was waiting for someone to hand her a sponsored NFT. They were even seen together this week at a MoMA event. Onlookers say Erica physically dissociated as if even she couldn’t believe her own storyline.

Erica and her golden retriever.

Erica isn’t a muse. She is a mirror reflecting Larry’s worst impulses in Prada boots. She tags brands like she’s assembling a ransom note. She makes influencer culture look like performance art—and not in a good way. If Anna is a painter with actual art world proximity, Erica is a sponsored post with cleavage.

Pelosini recently embarked on her own version of Roman Holiday—minus the charm, narrative arc, or basic self-awareness—while filming yet another 13-second cameo for Emily in Paris, the show that’s somehow more culturally offensive than it is plotless. Word on the street is Larry probably bankrolled the entire production just to keep her occupied (or quiet).

Afterwards, she flooded her Instagram with a carousel of chaotic “art” posts that read like a deranged scavenger hunt: a Bernini here, a Caravaggio there, a Basquait over there, intercut with herself in Miu Miu posing like she just discovered chiaroscuro. It was like Where’s Waldo if Waldo didn’t understand composition, context, or why anyone might care about art beyond its ability to match a handbag. And the worst part? She's Italian—she should get it. But alas, art history doesn’t stand a chance when your frontal lobe has been replaced by brand partnerships. Honestly, we don’t know how Larry puts up with it—unless she’s feeding him microdoses of Aperol between selfies.

Erica at the Met with Lare Bear in December of last year. We wonder where her clothes went. I guess this is where Chloe Wise can trace her recession slip era too.

Larry, let’s break it down. You are 80. You built an empire flipping Rothkos and Warhols like Pokémon cards. You convinced everyone that mega-galleries are sexy. That was impressive. But now you’re dating Erica Pelosini, whose resume sounds like a lost luggage claim: “Model. Stylist. Consultant. Brand partner. Possibly a sentient Fendi purse.” She has all the range of a Pinterest mood board stuck in 2012. She is not an insider. She is an interloper. A sponsored hallucination. Her idea of critical engagement is tagging Miu Miu while staring blankly into the MoMA sculpture garden.

Larry and Erica at the Oscars. I am so uncomfortable.

Erica doesn’t know who Lynda Benglis is. She’s never cried over a Joan Mitchell. She thinks post-minimalism is a new skincare line. Yet she clings to Larry’s arm like a charm bracelet reminding us all that powerful straight men will always pick aesthetics over insight, influence over intimacy.

But Larry, you could be different. You could pick me. I am not some gallery girl fantasy. I am a fully sentient, sharp-tongued academic with press creds, a grudge, and deep knowledge of how power, gender, and desire move through this industry. I know how to call out a board chair and style your socks at the same time. I’ve been in the trenches—Venice Biennale, Armory, Zona Maco during blackouts. I’ve ghostwritten your catalogs and know your curators. I understand art as power. And I understand you.

This is the image that set daddy over the edge and made me want to burn it all down.

I could teach you feminism—not the surface-level kind where you add a Mickalene Thomas show to the fall calendar. The real stuff. The kind that complicates desire, reorients power, and forces you to stop dating women whose brains are still baking. I could help you evolve from Daddy Warbucks to Daddy Woke.

Imagine it, Larry. You, me, a glass of Barolo, and a long overdue reckoning with your role in shaping art history through your libido. You’ve collected everyone but never been challenged by anyone. Until now. I am freelance, fabulous, and fully aware that your last great love affair was probably with tax evasion and a Basel afterparty in 1997.

But I see potential. Not to fix you, but to rebrand you. You are nearly a century old and dating women who still say “I’m baby.” It’s time to stop pretending it’s 2005 and that the primary market still rules. You need me. Not for love, but for legacy. I can teach you inclusivity. Power dynamics. The politics of Daddy. We could be so annoying together. And so hot.

I’m not here for the money, the status, or the Christie’s preview dinners. I’m here for the culture. The chaos. To say I rebranded Larry Gagosian from the inside. I am the art world’s final girl and your last chance at meaning something beyond your Rolodex.

So ditch Erica. Delete the archive of bronzed Euro-trash selfies. Let’s write a new chapter together. One that starts with a smirk, a Substack, and an age gap that finally works in reverse.

Larry, stop hoarding the 30-year-olds. Stop pretending your knees don’t crack when you sit down. Let me into your life—or at least your archive.

Call me, Lare Bear. Or better yet—email me back. Or at the very least, hire me to write an essay for your next major exhibit. You know daddy can write. You have viewed my substack hundreds of times.

Daddy’s waiting.