In the vibrant heart of New York City, Lucy, an ambitious assistant at the prestigious Woolf Gallery, is enamored with her captivating boss, Eva Woolf. Her day-to-day life brims with lively tales about Eva, which she passionately shares with her boyfriend, Max Vora, and her ever-supportive roommates, Amanda and Nadine. But when the much-anticipated gallery opening occurs, everything unravels. Lucy finds herself heartbroken as Max chooses his ex, Amelia, over her, and her job is abruptly terminated.
In the midst of this turmoil, a tipsy Lucy mistakenly hops into the vehicle of Nick, believing it to be her Lyft. During their drive, Lucy pours her heart out to Nick, who listens with empathy, providing a brief escape from her troubles. For weeks following her upheaval, Lucy isolates herself in her room while Amanda and Nadine gently coax her to confront her emotional turmoil. However, letting go of mementos from her past proves to be a challenge.
Lucy's predicament intensifies when she decides to trace Max and Amelia to a nearby eatery, where she is intercepted by Nick, averting potential further heartache. This unexpected encounter catalyzes a series of events that lead Lucy to the Chloe Hotel, a unique project initiated by Nick, transforming an old YMCA into a boutique hotel.
As they bond over their shared setbacks, Nick proposes a collaboration to establish the Broken Heart Gallery, a soothing space where New Yorkers can confront their emotional pain and forge connections through common experiences of loss. Their creative partnership flourishes as Lucy's inspiration is reignited, particularly when Nick surprises her with a special addition to the gallery wall, awakening her awareness of the healing power of storytelling.
Lucy’s social media followers become engaged with the gallery's mission as she shares meaningful moments and encourages others to release their keepsakes, showcasing the liberating experience of letting go. Together, Lucy and Nick embark on adventures through thrift stores and second-hand shops, tirelessly searching for treasures that embody the gallery's ethos. Their heartfelt discussions reveal personal stories, with Lucy sharing her family's artistic legacy and Nick reminiscing about the heritage that shaped his hotel ambitions.
Amid their progress, a chance meeting at a used bookstore has Lucy cross paths with Max once again, but she is swiftly whisked away by Nick, who claims they are off to a significant meeting about their burgeoning gallery. As they walk away, Max watches with a mix of confusion and curiosity about Lucy's new journey.
While Lucy immerses herself in the hotel-gallery, an enigmatic woman, Chloe, unexpectedly appears, disrupting the evolving dynamic with Nick. Later, Amanda, Nadine, and Marcos invite Nick and his wife to a vibrant birthday celebration, where Lucy reveals a magazine feature highlighting their project. As they join in a heartfelt rendition of "Don't Go Breaking My Heart," Marcos encourages Nick to embrace the potential blossoming between him and Lucy.
As the clock strikes 3 AM, Amanda and Nadine return from the festivities to find Max lurking outside. Tension thickens until Nick arrive bearing a cake, leading to a confrontation between the two men. Bolstered by her roommates’ unwavering support, Lucy stands strong as Nick faces a sudden financial setback. In a moment of desperation, he implores Lucy to dissolve her exhibition, but she resolutely refuses to succumb to adversity, pursuing alternative gallery options.
At lunch with Max, an unexpected suggestion arises regarding Eva Woolf as a potential sponsor, a revelation that surprises everyone. However, after deep contemplation, Lucy realizes that her past with Max is a chapter she needs to close. Meanwhile, Nick delivers exciting news; he has found a mysterious benefactor willing to finance their vision.
As the gallery’s opening nears, Lucy’s exhibit begins to take shape, with contributions from each of their diverse perspectives. During a heartfelt moment, she introduces Nick to her mother, Cheryl, who is grappling with the trials of dementia. Their connection is interrupted by Chloe's reappearance, causing Lucy to feel betrayed and uncertain.
Nick's attempts to mend fences regarding his link to Chloe fall flat, leading him to withdraw from the gallery opening to avoid overshadowing Lucy’s anticipated success. Just when despair threatens to take hold, Eva Woolf surprises everyone with a generous donation to Lucy’s exhibition—a poignant wedding ring symbolizing the journey of healing. Her words resonate deeply within the gallery: > “Pain is inevitable. It’s what you do with it that matters.”
As the emotional climax approaches, Lucy and Nick’s intertwined destinies come to light, culminating in Nick’s passionate revelation of a new venture called the Broken Hearts Hotel. Just as Lucy is poised to begin her narrative for the exhibition, Nick boldly pours out his feelings, allowing a beautiful connection to blossom as they confront their shared heartbreak together.
