Dree Hemingway – Romance & Reality

Born into one of literature’s loudest legacies, Dree Hemingway has spent her life navigating visibility across runways, film sets and online. As she enters the next phase of her career, she reflects on motherhood, public life and ritual – and how to build an interior world alongside it all.

It’s late afternoon on a Tuesday and the Chateau Marmont courtyard is humming. Dree is already there, half an hour early, folded easily into the noise. She’s found friends, claimed a sofa and ordered an iced Americano. I apologise for keeping her waiting. She laughs. “I looked at my calendar for like a second and totally messed it up.” We move to a nearby table and Dree considers another coffee. “Is that aggressive? It might be aggressive,” she asks, then orders one anyway. It’s an LA winter day that feels like summer and Dree is wearing a navy sweater, tan straight-leg trousers and a pair of black boots, a dark tan woven bag slung over her shoulder. Her blonde hair is loose and frames her makeup-free face.

Two minutes into our conversation, we’re interrupted by model Stella Maxwell, who stops to say hi before sitting nearby with friends. “It’s nice to have a little bit of buzz in LA. I lived in New York for 15 years and I miss that energy. Here it’s like you’re wading through water a little bit sometimes,” Dree says. Los Angeles, she adds, can be a difficult city for introverts – its quietness amplifying whatever you’re already feeling, its expansiveness offering an easy out. “I’ve had a couple of spontaneous nights recently that were so great. But now that I have a child, spontaneity is very different. You have to really pick and choose, which is beautiful in its own way. Day drinking is very fun and white wine is real for moms.” New York works the opposite way. “Because the city is so loud, it lifts you out of your shell. I get pure joy from a taxi driver yelling at another car. I’m like, ‘Oh, God bless. Show your feelings!’ It’s not as taboo to be cranky there. It’s healthy not to have to be so perfect and on point.”

The contrast between the two cities mirrors something Dree recognises in herself – a pull between exposure and retreat. She describes herself as an “extroverted introvert” i.e., loud and effusive in some rooms and easily overwhelmed in others. “I’m publicly a lot more outgoing than I am privately, and privately a lot more emotional than I am publicly. But at the same time, I’m genuinely pretty authentic to who I am, in and out.” She recognised that same duality in Daryl Hannah while preparing to play her in Ryan Murphy’s Love Story, which traces JFK Jr. and Carolyn Bessette’s relationship in the shadow of his earlier, highly public romance with Daryl. “I think she’s quite a private person. Even during that time when she was so much in the public eye, she was also very private, which gave room for gossip and storytelling.”

To prepare for the role, Dree read every article and watched every interview she could find, but avoided rewatching Daryl’s films: it wasn’t about acting the way she does on screen. The two have never met, but Dree’s mum, Mariel, was an actor at the same time and was sometimes mistaken for Daryl at the airport when she was a child. She found similarities between herself and the woman she was portraying, particularly in their love of animals and the environment. “I’m not quite on the activist side, but I am a huge earth loving, animal loving person.” While filming, Dree even returned to being vegetarian. “Not because I was method acting. But because I really admired it. She made me think about choices and values.”

Dree grew up on her mum’s film sets and at home was only allowed to watch Turner Classic Movies. “I was obsessed with Grace Kelly and Katharine Hepburn, all the Hepburns, Audrey Hepburn and Doris Day. 

I was just like, ‘I want to do that. I want to be on camera, I want to be a strong woman and I want to be an inspiration, in some way, to another little girl or woman watching me.’”

At 18, on a whim, she moved to Paris to pursue modelling. She knew no one, didn’t speak French and was there for a year without being hired. Instead, she learned “the art of being extra alone. It was really good for me.” A year later, an agency found Dree’s card and told her to move to New York. Her hair was bleached for a Vogue Russia editorial with Alasdair McLellan and Katie Grand and “everything started to flow in the right way from there.”

When Dree was 22, she met director Sean Baker over Skype and pleaded her case for a role in Starlet, a guerrilla production that would become her breakout. The film follows Jane, a young adult film actress who forms an unlikely friendship with an elderly widow in LA’s San Fernando Valley. “It was intense and just the most magical thing.” Set has always been Dree’s ‘happy place’, but the end of a project can feel disorienting. “There’s this underlying depression or loneliness you can’t quite pinpoint,” she says. “You’ve just spent so much time with these people and there’s no time for bullshit. You have to go in exactly as you are.” The comedown requires recalibration. “When I was single, I used to come home from a project and hibernate for a couple of days. Now I don’t really have that option. You really have to communicate how you’re feeling.”

The most famous Hemingway is, of course, the Pulitzer- and Nobel Prize-winning writer, Ernest. But growing up in Idaho and going by her father’s last name, Dree felt sheltered from any outward connotation, other than in English class when, forced to study her great-grandfather’s novels, teachers would ask if she could tell them stories. “I was like, ‘No, I think you probably know more than I do.’” The weight of her family history really registered when she took the Hemingway last name. “I used to have a lot of imposter syndrome. I’d ask my dad, ‘Are you sure it’s okay?’ I never wanted him to feel like he wasn’t good enough,” she says. “Then there’s also trying to prove that I’m also my own person, which I don’t think ever came from the public, I think it just came internally from me.”

Dree has signed on as executive producer of the upcoming film, The Hemingway Files, about the very end of her great-grandfather’s life when he was living in Idaho. “It’s going to be as close as we can get to the truth,” she says of the project. “It’s less about the great writer he was and more about someone’s inner world. I think it’s a story people don’t really know. It’s sensitive and there’s a simplicity and intimacy about it. Everything’s being really fine-tuned right now, but I’m really excited. I think it could be something really amazing.”

A true romantic who was ‘ruined’ by Baz Luhrmann’s Romeo + Juliet, she has always been adamant not to settle. “I got to an age where I was like, ‘I don’t want to try and be somebody for this person. If I like them, just be exactly who I am. Lay your bullshit on the table. Be like, ‘These are my things. I’m not perfect.’ I think it sets you up in the right way.”

A few days after we meet, Dree will be surrounded by spectacle in Paris, front row at Dior and Chloé. In her twenties, she admits she performed more in these spaces. Now, she no longer bothers. “I don’t know how to do that anymore, which is irritating in some capacity. But also, I think that’s okay. I think that’s just about getting older where you just kind of ground yourself in who you are, rather than trying to be something or someone you think you should be.”

At home, Dree disconnects by taking phone-free walks with her dog in the mountains, journaling at night and listening to film scores – Hamnet, Tom Ford’s A Single Man (“heaven”). Rosalía’s LUX and the Love Story soundtrack offer a different, but equally necessary kind of grounding – “dancing and being wild.”