Meet Jennifer and her female friends, all in different predicaments: L’dawn is going through a seven-year divorce; Mindy is broken up with her rock-star boyfriend (although they still have sex); and Pat Cisarano, a blues singer, is diagnosed with a brain tumor. Jen herself spends a lot of time traveling the world for work: she is free and “single” and struggling with "commitment phobia". She has a secret married lover in South Africa but decides to take a new boyfriend - Patrick, a Swiss man. What is this strange modern life all are living?

Jennifer’s biological clock rings an alarm. Jennifer fought for sexual freedom her whole life in lieu of family and security, but now wonders if she missed some essential female experience? No matter how free she thinks she is, she can’t shake the message she was raised with: that women need a husband to have children. Jen takes off around the globe to see how women from other cultures are dealing with the issue. She decides enough is enough: she will stop using birth control with her two men and let fate decide…

Jennifer returns home to a shocking message: her lover’s wife has found out about her affair. Her friends weigh in on the morality of relationships with married men. Meanwhile, Jen must pull herself together: Patrick is arriving for a vacation. Later in New York, she meets Paromita, a community organizer from India, who invites her to visit. She flies to Indian, where Paromita leads Jen on a surprising, sometime hilarious, exploration of sexual rules in Indian culture, making Jen reflect on her own “free” values…

Jen discovers she is pregnant but miscarries. Heartbroken, she heads for Russia where she meets Svetlana, whom she confides in about some unresolved secrets from her past. Sveta convinces Jen she must fly to Zurich to see Patrick, but can they see eye to eye about the miscarriage? Afterwards, she flies to Cambodia to meet Chanthol, who runs a shelter for trafficked women. There, Jen is pained to discover that women who are tricked into sex before marriage have little other choice than to become prostitutes…

Patrick and Jen renew their relationship and they realize that time is running out to have a child. They decide to try IVF -- In Vitro Fertilization. With Patrick in Zurich, Jen rushes into IVF in New York with the help of her close girlfriends. Finally, Patrick arrives for the big day of retrieval and implantation. But suddenly Jen’s Gram is hospitalized. As her mother, aunt and her gather around her dying grandmother, Jen begins to see the three women who raised her differently – and the result changes her life forever…