Kiss Her Once for Me

The novel alternates between present-day chapters and illustrated webcomic flashbacks, both narrated by Ellie Oliver, a 25-year-old bisexual, demisexual aspiring animator in Portland, Oregon. The webcomic episodes, posted anonymously on the platform Drawn2, recount the previous Christmas Eve, when a snowstorm trapped Ellie in the city with a stranger named Jack. They met reaching for the same book at Powell's City of Books, spent the day playing an "honesty game," and fell into an intense connection by nightfall. Ellie, who requires deep emotional trust before experiencing sexual attraction, was stunned by how quickly she opened up to Jack, a tall, butch Korean American woman with a half-moon smile and an unapologetic presence. They slow-danced on the Burnside Bridge, slept together in Jack's Airstream trailer, and Ellie believed she had found something lasting. But the next morning, while Jack showered, a woman named Claire appeared at the trailer, introduced herself as Jack's wife, and said she had encouraged Jack to have a one-night stand. Ellie fled before Jack could explain.

One year later, Ellie's life has collapsed. She was laid off from Laika Studios, the acclaimed animation studio, and now works as a barista at Roastlandia, struggling with debt, rising rent, and her neglectful mother Lindsey's constant demands for money. Her closest Portland friend is Ari Ocampo, a trans Filipina coworker, while her best friend, Meredith O'Reilly, is an aspiring lawyer in Chicago who worries Ellie has been emotionally frozen since losing both Jack and her career.

Everything shifts when Andrew Kim-Prescott, Roastlandia's wealthy landlord, reveals that his late grandfather's $2 million trust fund requires him to marry before inheriting. Ellie drunkenly suggests he find someone to fake-marry him; Andrew asks her directly, but she refuses. The next morning she wakes in his apartment to find a ring on her finger and a cocktail napkin outlining terms: She will pose as his fiancée, spend Christmas at his family cabin, receive 10 percent of the inheritance ($200,000), and divorce after 12 months. After consulting Meredith, Ellie agrees and quits her job. She begins posting a new webcomic called The Arrangement on Drawn2, fictionalizing her situation, and the series quickly attracts tens of thousands of readers.

At the Kim-Prescott cabin on Mount Hood, an enormous ski chalet, Ellie is overwhelmed by Andrew's family. His grandmothers, Meemaw and Lovey, envelop her in hugs. His mother, Katherine Kim, who plans activities on a laminated schedule, hangs a stocking with Ellie's name on the mantel. For someone who has never experienced a real family Christmas, the warmth is almost unbearable.

Then Andrew's sister arrives. "Jacqueline" is Jack. In a private conversation, Jack proposes they keep their history secret, dismissing what happened between them as "one day" that "didn't mean anything." Ellie agrees, though the words break her heart. Jack keeps her Airstream parked at the cabin as a personal retreat, a sign of her stubborn independence from her family's wealth.

The week unfolds around Katherine's traditions: snowball fights, cookie baking, carols, tree decorating. A love trapezoid emerges. Andrew confesses he and Dylan Montez, Jack's nonbinary best friend, hooked up during college summers and again the previous Christmas; he brought Ellie partly as a buffer. Forced proximity keeps pulling Ellie and Jack together. Jack teaches Ellie to roll cookie dough, standing close behind her. The family pushes them to kiss under the mistletoe, and though the contact is brief, Ellie holds on a beat too long.

Ellie discovers that Jack kept mementos from their day together: Ellie's blue scarf, the copy of Fun Home they reached for at Powell's, and a napkin drawing of Jack's hand. Jack admits she believed Ellie ghosted her and was the one left heartbroken. During a private drive, Jack explains the truth about Claire: Their marriage was already over when Jack met Ellie, and Claire's visit on Christmas morning, which Jack never knew about, destroyed everything before Jack could explain.

The arrival of Andrew's father, Alan Prescott, destabilizes the family. Alan insults Jack, lectures her about her attention-deficit/hyperactivity disorder, and refuses to participate in traditions. At a dive bar, Ellie learns the real reason Andrew needs the inheritance: Their grandfather wrote Jack out of the will entirely, leaving all $2 million to Andrew. Andrew's scheme is designed to secretly give Jack her share so she can open her dream bakery, the Butch Oven, without knowing she was disinherited. When Jack demands to know if Ellie loves Andrew, Ellie admits she does not, and Jack kisses her.

The kiss leads nowhere that night, because Ellie understands that acting on her feelings could cost Jack $1 million. Two days later, a blizzard strands them at a neighbor's empty cabin, where they chop firewood, dance to Celine Dion, and stop pretending. They sleep together, and in the morning, Jack challenges Ellie's deepest pattern: She argues Ellie didn't fail at Laika but quit, because her identity was so fused with perfectionism that imperfection felt like annihilation.

On the walk back, Ellie receives an email from an editor interested in publishing her webcomics as a graphic novel. She and Jack plan to tell Andrew the truth. But Jack discovers The Arrangement on Ellie's laptop while telling the family about the publishing opportunity, and its fictionalized plot exposes the deception. Andrew reveals the story about the will, but Jack stuns everyone: She already knew her grandfather disinherited her and built her business without a safety net. She tells them she didn't need saving; she needed support. Outside, Jack calls Ellie a "self-fulfilling prophecy" who kept lying because she assumed they would fail. She could forgive the deception but not Ellie's refusal to believe in them. Jack walks to the Airstream.

Ellie returns to Portland on Christmas Day. Meredith flies out, revealing she herself failed the bar exam but hid it, illustrating how Ellie's perfectionism affects those around her. Ellie recognizes the hole inside her cannot be filled by money or another person. She sets boundaries with Lindsey, moves into a room in a group house offered by Ari, signs with a literary agent, begins a new graphic novel, and finds a therapist. Andrew visits a month later to apologize, sharing that Katherine has left Alan and that he and Dylan are now together. He gives Ellie a contract guaranteeing her 10 percent of his inheritance whenever he marries, regardless of whom, along with a flyer for the Butch Oven's soft opening on Valentine's Day.

At the bakery, Ellie finds Jack surrounded by the dream she built: lavender walls, communal tables, a glass case full of pastries. In front of 50 people, Ellie tells Jack she loves her. Jack, moved but guarded, says she cannot take that risk again. Ellie accepts the rejection, gives Jack a framed drawing of the warehouse before its transformation, and walks into the snow.

Jack follows Ellie to the Burnside Bridge, honking her truck's horn. She tells Ellie the drawing moved her deeply, then reveals she sold the Airstream and moved in with Katherine, finally accepting help. She admits she loves Ellie too but fears losing herself again. Ellie promises never to ask Jack to diminish any part of who she is. They kiss on the bridge in the falling snow, and Ellie reflects that whether they last 12 hours or a lifetime, she will savor every second. They slow-dance on the Burnside Bridge, back in their snow globe, now big enough for everything they have become.