Twenty-six-year-old bull-rider Theo Silva makes eyes at an attractive woman at the gas station. Then he heads to his best friend and mentor Rhett Eaton’s ranch for dinner. He ends up behind the attractive woman on the road. She drives slowly through the snowy dark, irking Theo. He is shocked when she makes the same turn into Wishing Well Ranch. Upon arrival, she jumps out of her car and accuses him of following her—declaring his advances unwanted as she is married. Theo is amused and delighted by her spirit. Rhett emerges on the porch, revealing that the woman is Winter, Summer’s elusive sister. Theo is intrigued.

Winter joins Summer, Summer’s fiancé Rhett, and Rhett’s family and friends for dinner. Overwhelmed, Winter tries to stay calm. She meets Rhett’s brothers, Beau Eaton, Cade Eaton, Cade’s partner Willa Grant, and the Eaton brothers’ father Harvey Eaton. She also learns that Theo is a bull rider who trains and works with the Eatons on their ranch. Winter notices how adoringly Rhett looks at Summer and feels a glimmer of jealousy.

After dinner, Winter and Theo chat outside in the snow. Theo apologizes for earlier. Charmed, Winter finds herself flirting with him.

Theo texts with his mother Loretta, who’s out of town for the holidays with his sister Julia. After dinner at the ranch, he heads back to Rosewood Inn where he and Winter are both staying. He offers to drive ahead of her so she gets in safely. At the inn, Winter offers to buy him a drink as an apology for getting upset earlier.

Winter fields texts from her mother Marina about the breakup with Rob. Marina thinks Winter is being foolish leaving him, insisting she try to make it work.

At the Rosewood Inn bar, Winter opens up to Theo about her complicated family. Her dad Kip Hamilton had an affair with her nanny Sofia—with whom he had Summer. Then Sofia abandoned Summer to the Hamiltons. Marina treated Summer terribly, inciting enmity between the sisters from a young age. Winter regrets how her parents’ disputes upset her and Summer’s relationship. Theo listens attentively as she explains how others see her. Theo encourages her to stop caring so much. They flirt and tease each other, before writing a sexual contract on a coaster. They agree to sleep with each other one time, no strings attached; they also promise to keep their encounter a secret. Winter signs the contract with her maiden name Hamilton instead of Valentine.

In the morning, Theo tells Rhett he helped Winter get home safely and that she went to bed early. In reality, the two spent the night together.

At the gym Summer owns, Theo works out with Rhett. Theo tries focusing on his bull-riding goals but feels distracted remembering his night with Winter. He “see[s] a future” with her despite all of the one-night stands he’s had in the past (69).

Over the next few weeks, Winter fields more scolding texts from Marina about her relationship with Rob. Meanwhile, she develops a friendship with Sloane Winthrop, Rhett’s cousin and Jasper Gervais’s partner. They connect over their difficult pasts and new lives in Chestnut Springs. Sloane also helps Winter find a place to live in town.

One night, Winter starts to feel sick. She calculates her last period and last sexual encounter. Then she takes a pregnancy test and it’s positive. She remembers her struggle to get pregnant with Rob, and the miscarriage she had during their pregnancy. Even now, she feels relieved she didn’t have Rob’s baby. However, she feels happy now. Thinking of Theo and the future, Winter asks Sloane to let her into Summer’s gym after hours. She wants to keep the baby and thinks Theo will, too. At the gym, Winter tracks down Theo’s contact information. She leaves him several messages without reply. Finally she texts him to say she is pregnant with his baby. Theo simply thanks her for letting him know.

Eighteen months later, Winter is living in Chestnut Springs with her nine-month-old daughter Vivienne, nicknamed Vivi. She has told everyone she got pregnant after a one-night stand and doesn’t remember the father’s identity. She has enjoyed being with Vivi during her extended maternity leave, but also misses working in the emergency room, too. Her life isn’t easy, but she’s glad to be in Chestnut Springs.

One day, Winter leaves Vivi with Harvey so she can attend a rodeo event with Summer and Willa. She is anxious about being away from Vivi for the first time and even more upset when she finds out that Theo is riding at the event. She hasn’t heard from him since their last texting exchange. While watching him ride, she is overcome with anger and hopes he falls. When he does fall and injure himself, a guilty Winter races to his side. She is struck by Vivi’s resemblance to him as she checks his injuries. He regains consciousness and greets her as Tink—the nickname he gave her the night they met.

Theo is glad to see Winter’s face after his injury. They chat and flirt before he loses consciousness again. A while later, he wakes back up in the hospital after surgery. At his bedside, Rhett tells him Winter is fighting with ER staff about his care. Winter and Theo’s doctor enter the room, bickering about Theo’s rehabilitation. The doctor insists Winter should return from maternity leave if she is so invested in Theo. Theo is shocked that Winter had a child, as he’s hoped he could one day convince her to giving him a real shot at a relationship.