In 2002, Jennifer was 42-years-old, living the life she thought she had always wanted: based in New York, working as a filmmaker, surrounded by friends, with a married South African lover and a Swiss cinematographer boyfriend. But when her best friend was diagnosed with a brain tumour, she was forced to reassess her decision to stay single, shunning marriage, commitment and children. She decides to take her confusion and her camera out on the road to talk to women about their lives.