After finishing a set at her usual comedy venue, Donna Stern finds herself heartbroken when her boyfriend, Ryan, abruptly breaks up with her in the bathroom, revealing he is leaving her for one of her friends. This shocking revelation sends Donna spiraling into a deep depression. Following a drunken mishap during her next performance, where she bitterly lashes out at her ex, she unexpectedly encounters Max at a bar. Although Max is there on business, having missed her set, an undeniable chemistry sparks between them, leading to a one-night stand. However, the morning after, Donna slips away from Max's apartment without a word.
Weeks later, while trying on clothes, Donna becomes alarmed by breast soreness and suspects a potential pregnancy. A subsequent home pregnancy test confirms her fears. Seeking advice, she visits a Planned Parenthood clinic to arrange for an abortion, but the only available appointments coincide with significant dates—her mother’s birthday and Valentine’s Day. She ultimately opts for Valentine's Day.
As fate would have it, Max seeks out Donna at the bookstore where she works, leading to a series of awkward meetings. Their paths cross again when Max returns a book to Nancy, Donna's mother and a former professor of his. During a dinner, Donna contemplates revealing her pregnancy and abortion plans to Max but hesitates after he expresses a desire to become a grandfather someday. Later, she invites Max to her comedy show, but after the set gets canceled, she ends up with another man, Sam, but quickly realizes that evening is not what she wants.
In distress, Donna confides in her mother about her upcoming abortion, who comforts her by sharing her own experience with the procedure before Donna was born. Struggling with her emotions, Donna attempts to reach out to Max, leaving several voicemail apologies and expressing her need to talk. Determined to have a candid discussion, she invites him to her next performance, but as she nervously takes the stage to tell the audience about her pregnancy, Max walks out.
However, on the day of her abortion, a thoughtful Max shows up at her place with flowers, offering to accompany her to the clinic. There, he reassures her of his support and clarifies that his earlier remark about wanting to be a grandfather was meant for the distant future, rather than as an immediate expectation. Following the procedure, they return to Max's place, where he prepares her a comforting cup of tea, and the evening culminates in watching the classic film Gone with the Wind, suggesting a burgeoning connection between them amidst the tumultuous events of their lives.
