Accidentally on Purpose follows Billie (Elfman), a San Francisco movie critic in her 30s. Billie meets Zack (Jon Foster), a chef in his 20s, at a local bar and they have a one-night stand at a friend's apartment. She soon finds out that she's pregnant from the fling. Billie decides to keep both her baby and her new beau, while dealing with her boss, James, who wants to resume their relationship after being humiliated. Before the story began, she had hoped that James would ask her to marry him, but he told her that he wasn't ready because he was married once before.

Thanks to this unexpected arrival, Billie and Zack have agreed to live together platonically, since the only place that Zack has called home was his van. While Billie receives encouragement and advice from her party girl best friend (and fellow journalist) Olivia and her conventional younger married sister Abby, she also has to deal with Zack's freeloading friend Davis, among others, when they start turning her place into a frat house, leaving Billie to question whether she's living with a boyfriend, a roommate, or if she just has a second child to raise.

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