Jessica Stein (Jennifer Westfeldt) is a sensitive, but neurotic, New York journalist who is at the end of her emotional rope. Her brother Dan (David Aaron Baker), is engaged. Her best friend and co-worker Joan (Jackie Hoffman) is pregnant. On top of that, Jessica hasn't dated in a year, and she can't sleep. After an optimistic but nightmarish dating spree, which is set up by her overbearing and meddlesome mother Judy (Tovah Feldshuh), Jessica decides she needs a change in her life.