'Kissing Jessica Stein' and the fluidity of sexual attraction

Discover the portrayal of a lesbian relationship in 'Kissing Jessica Stein' at the Atlanta Jewish Film Festival.

Published on Feb. 16, 2026

Got story updates? Submit your updates here. ›

The 2001 romantic comedy 'Kissing Jessica Stein' is being screened at the Atlanta Jewish Film Festival, with co-writer and lead actress Jennifer Westfeldt in attendance for a Q&A. The film, which was praised for its portrayal of a lesbian relationship, is explored through the lens of how it addresses the fluidity of sexual attraction.

Why it matters

While some critics at the time felt the film avoided serious questions about the same-sex relationship, a closer look reveals that 'Kissing Jessica Stein' is more about the fluidity of sexual attraction than a traditional lesbian love story. The film's exploration of this theme, and its willingness to let the protagonists explore their sexuality, is seen as a triumph by many in the LGBTQ+ community.

The details

The film stars Jennifer Westfeldt as Jessica, a neurotic and perfectionist copy editor, who answers a personal ad placed by Helen, played by Heather Juergensen. Helen is described as cool, casual and adventurous - the opposite of Jessica in many ways. The two women embark on a romantic and sexual relationship, but the film's ending, where Helen breaks up with Jessica and Jessica reconnects with her toxic male ex, has been criticized by some queer viewers as a letdown.

  • The film 'Kissing Jessica Stein' was released in 2001.
  • The film is being screened at the Atlanta Jewish Film Festival on February 21, 2026.

The players

Jennifer Westfeldt

Co-writer and lead actress of 'Kissing Jessica Stein', playing the titular role of Jessica.

Heather Juergensen

Co-writer of 'Kissing Jessica Stein' and actress playing the role of Helen.

Tovah Feldshuh

Actress playing the role of Jessica's Jewish mother in the film.

Scott Cohen

Actor playing the role of Josh, Jessica's toxic male ex-boyfriend and boss.

Got photos? Submit your photos here. ›

What they’re saying

“If [sex] really meant anything to either one of them … the comedy would be more difficult, or in a different key. We can laugh because nothing really counts for anything.”

— Roger Ebert, Film Critic (Chicago Sun-Times)

“Watching the film recently, I felt that same frustration. Unlike those critics, I felt like Jessica and Helen might be able to make it work. Even knowing the end, I believed in the evolution of their romantic and sexual relationship, and the fact that it doesn't work out is devastating.”

— Sammie Purcell, Writer (roughdraftatlanta.com)

What’s next

Co-writer and lead actress Jennifer Westfeldt will be in attendance for a Q&A session following the screening of 'Kissing Jessica Stein' at the Atlanta Jewish Film Festival on February 21, 2026.

The takeaway

While 'Kissing Jessica Stein' may not have fully landed its portrayal of a same-sex relationship for some critics, its exploration of the fluidity of sexual attraction is seen as a triumph by many in the LGBTQ+ community. The film's willingness to let its protagonists explore their sexuality, even if the ending is frustrating, is a testament to its nuanced and thoughtful approach to this complex topic.