Mike Flux, portrayed by Steve Zahn, is the dedicated night manager at his parents' motel, where he undertakes a myriad of tasks from cleaning rooms to maintaining the pool. His life is rather solitary, characterized by an absence of friends and a profound sense of loneliness. Everything changes when he encounters Sue, played by Jennifer Aniston, who is staying at the motel for a weekend getaway. Captivated by her charm, Mike develops a crush and attempts to break the ice by delivering a bottle of wine, claiming it to be a welcome gift from management. Though taken aback by his approach, Sue invites him in for a brief moment.
The next day, Mike shows up again, this time with champagne. This encounter leads to a flirtatious moment where, after paying her a compliment about her looks, Sue humorously questions the effectiveness of his line before allowing him to touch her butt. As fate would have it, the two end up together for a passionate encounter in the laundry room before she departs the next day. Realizing his feelings for Sue, Mike unexpectedly flies to her home in Baltimore to spend the day with her, participating in her activities, including a soccer game and even visiting a homeless shelter where she distributes meal vouchers.
Although Sue is initially surprised by his visit, she welcomes him for a night. The next morning reveals Mike's precarious situation, as he only purchased a one-way ticket, leaving him stranded. Their time together fosters a friendship, and they share moments of joy at an amusement park, and through yoga sessions, and discussions about her aspirations to create a soup kitchen. Tragedy strikes when Mike's mother, played by Margo Martindale, falls ill and eventually passes away just as Sue decides to leave, expressing doubts about a long-term relationship.
Determined to pursue his dreams and win Sue back, Mike discovers she has rekindled her romance with her previous boyfriend Jango, a character brought to life by Woody Harrelson. He sets out for Aberdeen, Washington, where Jango has become a successful businessman. With limited resources, Mike seeks shelter at a local football field while finding work at a Chinese restaurant, where he strikes a friendship with Al, the owner's son. Motivated by a mix of hope and desperation, Mike attempts to make a grand gesture by skydiving into Jango’s pool to surprise Sue. However, the encounter with Jango leads to tense confrontations and a subsequent dinner invitation extended by Jango, where Sue introduces Mike as an artist she met previously.
As the drama unfolds, Jango becomes increasingly aware of Mike's feelings for Sue and threatens him. Despite this, Mike finds the courage to sing a heartfelt song outside Sue's window. However, the situation turns heart-stopping when Sue shares news of her pregnancy and her impending marriage to Jango, insisting she needs stability in her life. Devastated, Mike tells her to leave, prompting his emotional retreat to a Buddhist monastery, where he confronts his unresolved feelings.
After four months of reflection, Mike returns to the motel, now solely managed by his father, who offers him the reins to the establishment. In a transformative decision, Mike resolves to convert the motel into a homeless shelter, fulfilling Sue's dream. In a twist of fate, he learns from Jango that Sue has left him and is back with her mother. Seizing the opportunity, Mike visits Sue, only to find her remorseful about their past and eager to reconnect. Their heartfelt reunion culminates in Mike professing his love and an earnest desire to care for her and their unborn child. As they embrace, hope shines anew, hinting at a fresh start for both.
