In 2003, Mirabelle Buttersfield (Claire Danes), an aspiring artist from Vermont, finds herself working at the evening gloves counter in Saks Fifth Avenue, Beverly Hills. Her life is a blend of the ordinary—marked by her futon furniture and an aging pickup truck—and the weighty realities of student debt ($39,452) and a reliance on antidepressants. This stable yet monotonous existence is suddenly turned upside down by the entrance of two very different men.
Jeremy (Jason Schwartzman), a socially awkward and broke graphic designer for an amplifier company, crosses paths with Mirabelle in a laundromat. Longing for genuine connection, Mirabelle decides to give Jeremy a chance. However, their date quickly fizzles out when they opt to sit outside a theater, merely staring at it instead of going in—especially since the tickets cost $10 each. Their brief sexual encounter is equally dismal, as Jeremy arrives unprepared, bringing a mint instead of a condom, and then needing to borrow one from Mirabelle's neighbor. Their moment is humorously interrupted by her cat, leading to a swift conclusion.
On the other hand, Ray Porter (Steve Martin), a sophisticated and well-off man in his 50s, approaches Mirabelle with charm that captivates her. After buying gloves from her counter and inviting her to dinner, their connection grows. Despite the age difference and his previous divorce, Ray is well-established with homes in both LA and Seattle. However, after they share a night together, Ray informs Mirabelle that he isn't looking for a serious relationship due to his frequent travels. Their interpretations of his words differ significantly: Ray believes he has made his intentions clear to his psychiatrist, whereas Mirabelle thinks he desires to see her more frequently.
As Mirabelle and Ray engage in an extended affair, Jeremy attempts to reconnect with her before embarking on a new journey as a roadie for the band Hot Tears, but she turns him down due to her commitment to Ray. On tour, Jeremy is introduced to self-improvement, learning how to better connect with women. Meanwhile, Mirabelle's devotion to Ray deepens, as he showers her with lavish gifts, even paying off her student loans in lieu of offering emotional support. As her depression resurfaces—compounded by the fact that she has stopped taking her antidepressants—Ray steps in, taking her to the doctor and increasing her dependency on him. He surprises her with a trip to New York, complete with a fitting at Armani.
However, during a business dinner, Ray reconnects with an old flame, Christie Richards (Rebecca Pidgeon), and ends up giving in to her advances. When he reveals this to Mirabelle, she is heartbroken and abruptly decides to leave the New York trip behind, choosing instead to retreat to the comfort of her hometown, where her parents, Dan (Sam Bottoms) and Charlotte (Frances Conroy) are there to support her. Ray then reaches out, hoping for reconciliation, and invites her to a party in New York. At the gathering, Mirabelle feels isolated and out of place, and when Ray seeks intimacy in their hotel room, she rejects him.
Once back in California, Mirabelle runs into Jeremy on her way to an art show, and they attend the event together. Confusion arises when her co-worker, Lisa (Bridgette Wilson-Sampras), mistakenly identifies Jeremy as Ray based on Mirabelle’s new, stylish clothing. Unbeknownst to Mirabelle, Jeremy's newfound self-improvement has caught the attention of those around them, and Lisa ends up having an intimate encounter with him. Meanwhile, Mirabelle returns to Ray, only to be blindsided the next morning when he reveals his intentions to look for a bigger house, implying a desire for children in the future.
Heartbroken, Mirabelle finally puts an end to her relationship with Ray. After a brief period of grief, she leaves her Saks job and takes up a position at an art gallery. In a new, genuine pursuit of love, Jeremy re-approaches Mirabelle and they begin to bond. She is eventually invited to showcase her artwork at the gallery, where Ray shows up with his new girlfriend, a gynecologist. The contrast between Mirabelle’s relationship with Jeremy—marked by pride and affection—and her strained conversation with Ray is palpable. Ray expresses regret for how he treated her and admits to having loved her. Touched by his words, Mirabelle runs into Jeremy's arms, highlighting the stark difference between her current happiness and her past relationship with Ray, who observes the couple and laments the loss of what could have been, even as he kept Mirabelle at "arm's length" to avoid the pain of their eventual separation.
