Accidentally On Purpose is a comedy starring Golden Globe Award winner Jenna Elfman as Billie, a single woman who finds herself "accidentally" pregnant after a one-night stand with a much younger guy and decides to keep the baby and the guy. A newspaper film critic, Billie is barely surviving a humiliating breakup with her charming boss, James (Grant Show), who's still trying to resume their relationship. Suddenly expecting a child with her "boy toy," Zack (Jon Foster), Billie and Zack make an arrangement: to live together platonically. Billie's party girl best friend Olivia (Ashley Jensen), and Abby (Lennon Parham), her conventional, younger married sister, eagerly look forward to the new addition and offer their own brands of advice and encouragement. But when Zack and his freeloading friends, including Davis (Nicolas Wright), start to turn her place into a frat house, Billie isn't sure if she's living with a boyfriend, a roommate, or if she just has another child to raise.