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BOOKS
The Heirloom
A new novel by Jessie Rosen ’05 offers a twist on the fairy-tale ending of a marriage proposal.
Fall 2024
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Jessie Rosen ’05 has been a working screenwriter in Hollywood for years now, but she celebrated a new creative milestone last summer with the publication of her first novel for adults. The Heirloom is a love story about a young woman named Shea who gets an intense case of cold feet after her longtime boyfriend proposes with a vintage engagement ring while asking her to marry him.
According to her Italian family’s superstitions, an heirloom ring passes down to the next wearer the “energy” from the prior marriages it was used in, so Shea embarks on an international quest to learn the love stories of the women who owned the ring before her.
The Heirloom explores societal expectations of marriage, and asks what love stories mean, both to the outside world and to the people in them. The novel has received positive critical notice, with Kirkus Reviews calling it “an earnest exploration of the trauma that can follow the children of divorce into adulthood,” and The Knot including it on a list of great books to read on your honeymoon.
Rosen said that Shea’s concerns about the ring, based on actual beliefs that she grew up with, allowed her to play with gender stereotypes about the fear of commitment. “The concept of cold feet is very male-dominated,” Rosen said. “I thought that women deserved that opportunity to freak out.”
Rosen first attracted attention as a writer in 2007 with the well-received blog 20Nothings, which chronicled her experiences as a young person taking on the world. The project grew steadily over time, with Time naming it a top twenty-five blog, and Forbes honoring it as a top ten website for millennials. With Hollywood showing interest in a movie or TV adaptation of the blog, Rosen moved to Los Angeles in 2010. The adaptation never materialized, but she found success anyway on the West Coast.
In 2012, she created the influential stage show Sunday Night Sex Talks, featuring performances from prominent comedians including Rosen’s fellow Eagle Cameron Esposito ’04. The show caught the attention of the sketch comedy powerhouse Upright Citizens Brigade, which began hosting it on their stage in LA. Rosen then launched a second version in New York. More recently, she’s become a showrunner on the Amazon Prime show The Baxters, which came out this year.
Rosen acknowledged feeling intimidated when it came to writing a novel and facing the vastness of an empty page. But The Heirloom was a natural story for her to tell, she explained, since it was inspired by her boyfriend proposing to her. When she admitted to friends that she wasn’t sure she was ready for marriage, they often responded by wondering whether the boyfriend was the problem. (He’s now her husband, by the way.) When women wrestle with whether they’re interested in the institution of marriage, Rosen said, “the assumption is that you’ve picked the wrong person. I thought it was important to say, ‘You can still make the decision to enter into partnership, but shouldn’t you go in very certain about the I in I do?’”
The Heirloom has romance and love at its center, but it’s also an examination of what makes couples last, or not. “I think my obsession with culture and psychology and sociology mixes with archetypes of romance and rom-coms, and wants to poke and prod a little bit,” Rosen said. She said some rom-coms are “perfect” stories, but she’s always wondered what happened after the credits rolled. “I always wanted five more hours with the characters,” she said, “to be like, What? Why? What’s going on behind there? Why do you feel that way?”
Rosen’s first novel, a young adult title called Dead Ringer, was published in 2015. It was during the pandemic that her manager suggested she write a novel for adults. It was an escapist thrill during the depths of quarantine, she said, to write about someone jetting off to Europe to have adventures. “I was writing all the places that I wanted to be,” she said. “I was having a bad time, and it was way more fun to write about Portugal.”
The Heirloom is the first release in a two-book deal Rosen signed with G. P. Putnam’s Sons, and she’s now at work on her follow-up novel, All the Signs, about a woman who’s never believed in astrology but starts to change her mind after a psychic reading proves startlingly accurate about her life during a challenging time. Like The Heirloom, “it’s really about a person’s relationship with self-actualization and knowing themselves,” Rosen said. “It’s exploring this idea of how we get disconnected from knowing ourselves—and what it takes to reconnect.” 
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