Jessica Stein (JENNIFER WESTFELDT) is a 28-year-old copy editor who lives in New York. Rather picky about men, she hasn't dated in a year -- much to the chagrin of her matchmaker mother, Judy (TOVAH FELDSHUH) - although she was once in a long-term relationship with Josh Meyers (SCOTT COHEN) who now happens to be her boss.
When Jessica's pregnant coworker, Joan (JACKIE HOFFMAN), reads her one of the personals from the paper, Jessica thinks the person sounds perfect for her. Since a woman seeking a woman wrote it, however, Jessica initially dismisses it. Yet, throwing all caution to the wind, she then decides to meet Helen Cooper (HEATHER JUERGENSEN), an assistant director at an art gallery.
Having the same problem finding the right person, Helen had her gay friends Martin (MICHAEL MASTRO) and Sebastian (CARSON ELROD) help write the personal ad for her, and she's instantly attracted to Jessica upon meeting her.
While Helen is a practicing bisexual, any sort of same sex behavior is foreign to Jessica, and she's embarrassed, awkward and unsure of how and whether to proceed. The two eventually become lovers, however, and must then deal with the happiness of finding love contrasting the pitfalls of such a relationship, including Jessica's reluctance to let anyone know of it.