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Caitlin Cronenberg and Jessica Ennis's The Endings started from the kind of intimate conversation that can feel unique to female friendship – two young women talking unreservedly about their former joys and embarrassments in love.

Photographer Caitlin Cronenberg and art director Jessica Ennis are wary of generalizing about breakups and gender. Discussing The Endings, their captivating book of photographic stories centred on the theme of breaking up, they hem and haw over whether the project expresses a distinctly female experience. The subjects they’ve chosen are all women: twenty-eight prominent actresses, including Hollywood stars such as Julianne Moore, Keira Knightley and Jennifer Jason Leigh. The actresses are ethnically diverse and span five generations. In every scenario, the ex-partner is absent and their gender unknown. So, save for a few background characters, the book has no images of men.

“There’s probably no denying that women really care about breakups,” Ennis says with a shrewd smile. “I mean, even in discussing the book with other women, it’s something they really want to talk about.”

“We know how to tell this side of the story,” Cronenberg adds. “We feel the depth of these characters because we’ve experienced these stories or our friends have experienced these stories.”

The Endings started from the kind of intimate conversation that can feel unique to female friendship – two young women talking unreservedly about their former joys and embarrassments in love. Cronenberg and Ennis are both from Toronto and were put in touch by a mutual friend about a decade ago when Ennis, based in New York, was looking for a photographer for an art project. They became fast friends and in a chat that had them rehashing their worst breakups from high school, they realized that their memories were full of visual drama. They started to imagine how artfully these scenarios would translate into photographs.

As they produced the book, which took seven years from start to finish, their pasts weighed heavily upon the project. When an early shoot found them outside of Ennis’ childhood home in Thornhill, Ont., a suburb north of Toronto, burning her actual ex-boyfriend memorabilia from high school, she chuckled at the overlap between life and art.

“We did it in a forest with a fire extinguisher,” Ennis says of the shoot with Canadian actress Sarah Gadon. “We did Sarah’s hair and makeup in my childhood bedroom. The guy who had loaned us his car hung out with us the whole time.” She laughs. “It was really not the most professional operation.”

The two artists learned to become more professional as the project evolved, but maintain that their guerrilla approach to shooting was always key to the book’s spirit. This rawness is most palpable in some of the atmospheric outdoor images, many taken after nightfall and depicting despondent young women adrift in shadowy urban sites. They’re photographs that suggest an overlap between heartbreak and danger, as though a lovelorn woman forgets reality and risk. A particularly memorable series cuts close to Cronenberg’s heart: In Girls Are Heinous, a young woman (Ophelia Lovibond) dressed in costume wings wanders through a London tunnel under strips of fluorescent light. Cronenberg says the series relates her own story of unrequited love as a teenager. She smiles ironically and assures me she’s gotten over it, but at the time “I felt like I’d been punched in the chest,” she says.

Typically, Ennis and Cronenberg wrote each scenario ahead of time – a bare-bones script that would give the actress a character and situation. But when Cronenberg approached Julianne Moore with the idea of depicting an illicit relationship with a much younger man, Moore had ideas of her own. “She said she’d done that already and wanted to tell a story she hadn’t told yet – the one where you never find love at all,” Cronenberg explains.

They shot the sequence, titled This is What it Is, in a beautiful house in Chelsea in New York. “It’s hard to direct someone you respect so much,” Cronenberg says reverently. “We wanted to show her loneliness inside the house, this lavish home that she’d built herself – everything this woman had done had been only for herself.”

Over the course of the seven years it took to produce the book, its creators’ lives underwent major changes. Cronenberg got married and Ennis got divorced. Both of them had a child. Ennis started dating again and some of the ideas explored in the photos were situations she was working through in real time. She points to an image of Canadian actress Nina Dobrev waiting in the lobby of Brooklyn apartment complex, then another of her hiding behind a graffiti-covered phone booth.

“This is ridiculously personal, but I went on this one 18-hour date with someone – it was one of those things where it was this perfect crazy date and I found myself looking on social media, being consumed by someone I hardly knew, the idea of what something could be,” Ennis says.

Ennis is also an avid journal writer, and many of the series’ poetic titles are taken directly from the pages of her diary. She references To All the Men Who Left Me Here as an example – a series of haunting images of Swedish actress Noomi Rapace lying on the floor in an ornately decorated living room. “It’s that feeling when all your breakups start to blur into one – there’s only one man,” Ennis says. “I think a lot of people share that sentiment.”

One of the project’s chief pleasures, and surprises, was how much all the women who worked on the book bonded over the material. “We’d all hang out for hours after, legitimately discussing our break-up stories,” Ennis says.

Cronenberg adds, “During the shoot, it was Jess and me in the room with the actor – the crew would leave. It was this incredibly intimate moment with the actress because they were pouring themselves into this character and we were watching. After we felt like hugging them and sitting around and having some tea and talking it through. It was therapeutic – in a way – for everybody.”

The Endings is an important professional milestone for both artists, who produced the entire book themselves, overseeing everything from the logistics of shooting in four cities – Toronto, New York, Los Angeles and London – to the smaller details of ordering water for the crew. They’ve also co-directed a short film to coincide with the book’s release – it stars Canadian actress Melanie Scrofano and will premiere at TIFF. But when Ennis suggests that the major lesson learned from the project has to with letting go of the notion of perfection, Cronenberg agrees wholeheartedly. She says that the decision to occasionally disregard technical conventions of excellence was an artistic revelation.

“We would look through images and say, ‘well, this is blurry, but I love it and it’s so powerful,’” Cronenberg explains. “That was really exciting for us – there was no one telling us what to do.”