''Kissing Jessica Stein'' is a 2001 American

independent Independent or Independents may refer to: Arts, entertainment, and media Artist groups * Independents (artist group), a group of modernist painters based in the New Hope, Pennsylvania, area of the United States during the early 1930s * Independe ...

romantic comedy Romantic comedy (also known as romcom or rom-com) is a subgenre of comedy and slice of life fiction, focusing on lighthearted, humorous plot lines centered on romantic ideas, such as how true love is able to surmount most obstacles. In a typic ...

film, written and co-produced by the film's stars,

Jennifer Westfeldt Jennifer Westfeldt (born February 2, 1970) is an American actress, screenwriter, director, and producer. She is best known for co-writing, co-producing, and starring in the 2002 indie film '' Kissing Jessica Stein'', for which she received an ...

and

Heather Juergensen Heather Julia Juergensen (born January 2, 1970) is an American actress and writer. Life and career Juergensen was born and raised in Brooklyn, New York. She graduated from Stuyvesant High School in 1987. Soon after, she began writing and perfor ...

. The film also stars

Tovah Feldshuh Terri Sue "Tovah" Feldshuh (born December 27, 1948) is an American actress, singer, and playwright. She has been a Broadway star for more than four decades, earning four Tony Award nominations. She has also received two Emmy Award nominations f ...

and is directed by

Charles Herman-Wurmfeld Charles Herman-Wurmfeld (born July 5, 1966) is an American film and television director A television director is in charge of the activities involved in making a television program or section of a program. They are generally responsible for ...

. It is one of the earlier film appearances of actors

Jon Hamm Jonathan Daniel Hamm (born March 10, 1971) is an American actor. He is best known for his role as Don Draper in the period drama television series '' Mad Men'' (2007–2015), for which he won a Golden Globe Award for Best Actor in a Televis ...

and

Michael Showalter Michael Showalter (born June 17, 1970) is an American comedian, actor, director, writer, and producer. He first came to recognition as a cast member on MTV's ''The State'', which aired from 1993 to 1995. He and David Wain created the ''Wet Hot ...

. The film is based on a scene from the 1997

off-Broadway An off-Broadway theatre is any professional theatre venue in New York City with a seating capacity between 100 and 499, inclusive. These theatres are smaller than Broadway theatres, but larger than off-off-Broadway theatres, which seat fewer th ...

play by Westfeldt and Juergensen called ''Lipschtick''.

Plot

28-year-old Jessica Stein is an attractive, Jewish, neurotic

copy editor Copy editing (also known as copyediting and manuscript editing) is the process of revising written material ( copy) to improve readability and fitness, as well as ensuring that text is free of grammatical and factual errors. ''The Chicago Manual o ...

at a

New York City New York, often called New York City or NYC, is the List of United States cities by population, most populous city in the United States. With a 2020 population of 8,804,190 distributed over , New York City is also the L ...

newspaper. Her brother Dan has just gotten engaged, her best friend Joan is about to start a family, and her mother Judy is worried that Jessica will end up alone. Having endured several awful blind dates searching for Mr. Right, Jessica's interest is piqued by a personal ad that includes her favorite quote about relationships by

Rilke René Karl Wilhelm Johann Josef Maria Rilke (4 December 1875 – 29 December 1926), shortened to Rainer Maria Rilke (), was an Austrian poet and novelist. He has been acclaimed as an idiosyncratic and expressive poet, and is widely recogn ...

. Jessica discovers it is in the " Women Seeking Women" section of the newspaper. The ad was placed by Helen Cooper, who works at an

art gallery An art gallery is a room or a building in which visual art is displayed. In Western cultures from the mid-15th century, a gallery was any long, narrow covered passage along a wall, first used in the sense of a place for art in the 1590s. The lon ...

. Dissatisfied with unfulfilling sex with men, Helen is looking to try something different and decides to experiment with dating women at the encouragement of her gay friends. Jessica replies to the ad, but she becomes apprehensive when she meets Helen, then apologizes and exits. Helen chases after her and persuades her to stay for one drink. The two discover they get along well and have a lot in common; they have dinner. Helen challenges Jessica's assumptions about what will make her happy and passionately kisses her goodnight. Jessica and Helen start dating and awkwardly

make out Making out is a term of American origin dating back to at least 1949, and is used to refer to kissing, including extended French kissing or heavy kissing of the neck (called ''necking''), or to acts of non-penetrative sex such as heavy pett ...

on Helen's sofa afterwards. The usually uptight Jessica gradually becomes more happy, confident, and carefree; this is noticed at her workplace and attracts interest from her boss, Josh. Jessica evasively says that she has not found a boyfriend. Helen, meanwhile, is falling in love with Jessica and grows frustrated that their relationship is not moving faster. Judy invites Jessica and Helen to dinner at their holiday house, where she tries to set them each up with a computer executive and Josh, respectively. A thunderstorm causes Helen to sleep over in Jessica's old bed, where she and Jessica have sex for the first time. The two of them are happy together, but Jessica stays closeted about her new relationship, refusing to bring Helen as her date to Dan's wedding for fear of what others will think. Devastated, Helen says she cannot accept being treated as a shameful secret, and tearfully breaks off their relationship. As Dan's wedding approaches, Jessica sinks into a deep depression and goes to see Judy, who tells her that she is a perfectionist who always quits things if they are not perfect, even if they make her happy. Judy takes a deep breath and says that Jessica should not let this ruin her chances at happiness with Helen, who seems like "a lovely girl". Realizing her mother has accepted her sexuality, Jessica breaks down into tears of joy. Jessica apologizes to Helen and invites her to be her date for Dan's wedding. Helen is a hit at the event and warmly welcomed into the family. Josh, meanwhile, has realized that he has been in love with Jessica for some time, and shares his feelings with her after the party. Jessica awkwardly but firmly explains that she is in a relationship with Helen and departs with her, leaving Josh speechless. A few months later, Jessica and Helen are living together in Helen's apartment, where their sexual relationship begins to fade. Helen realizes that Jessica views her as a best friend and roommate more than a lover, and says that she needs more than Jessica is able to give. A fight ensues; Jessica implores Helen to accept their relationship as-is, but Helen remains steadfast to her need for a partner who satisfies her sexually, and the two split for good. Several months later, Helen is happily living with another woman. Jessica is a more calm and content version of her former self, having taken the positive things she learned from her time with Helen and applied them to her own life. She puts up fliers in a bookstore seeking a new roommate, missing the flirtatious interest of the attractive store owner. She spots Josh among the bookshelves, whom she has not seen since she left the paper to focus on her painting. They have a friendly catching-up, and she tells him that Helen dumped her, which was tough, but ultimately made her a better person. She gives Josh a flyer with her email on it. Later, Jessica meets up with Helen—the two women now solidly friends—and joyfully tells her that she is going on a date with Josh.

Cast

as Jessica Stein *

as Helen Cooper * Scott Cohen as Josh Myers *

Jackie Hoffman Jacqueline Laura Hoffman (born November 29, 1960 in Queens, New York City) is an American actress, singer, and comedian known for her one-woman shows of Jewish-themed original songs and monologues. She is a veteran of Chicago's famed The Second ...

as Joan Levine * Allen Fitzpatrick as Matthew Levine, Joan's Husband *

as Judy Stein * Robert Ari as Sidney Stein *

Brian Stepanek Brian Patrick Stepanek (born February 6, 1971) is an American actor. He is known for his role as Arwin Hawkhauser on the Disney Channel Original Series ''The Suite Life of Zack & Cody'' and Brian on '' Brian O'Brian''. He was also a Sector Seve ...

as Peter *

John Cariani John Edward Cariani (born July 23, 1969) is an American actor and playwright. Cariani is best known as the unwavering forensic expert Julian Beck in ''Law & Order''. On stage, he earned a Tony Award nomination for his role as Motel the Tailor in t ...

as Chuck *

Michael Mastro Michael R. Mastro (born June 1, 1925) is an American real estate developer, who was in business for forty years managing apartments and mid-size office parks in Seattle. He declared bankruptcy in 2009. Mastro and his wife, Linda, a former Bellev ...

as Martin * Carson Elrod as Sebastian * Ben Weber as Larry * Nick Corley as Howard *

David Aaron Baker David Aaron Baker (born August 14, 1963) is an American actor whose credits stretch across theater, film, television and audiobooks. Biography On Broadway, he is most prominently known for his starring role as "Prince Dauntless" opposite Sarah ...

as Danny Stein * Jennifer Carta as Rachel, Danny's Fiancée * Peter Hirsch as Stanley Schoenberg *

as Charles * Esther Wurmfeld as Grandma Esther * Michael Ealy as Greg *

as Stephen *

Tibor Feldman Tibor Feldman (born April 25, 1947) is an American actor, having played roles in movies, television shows, television commercials, and stage plays. He has appeared in television dramas including: ''Law & Order'', ''Conviction (2006 TV series), ...

as Roland * Ilana Levine as Helen's New Girlfriend *

Alysia Reiner Alysia Reiner is an American actress. She is best known for playing Natalie "Fig" Figueroa in the Netflix comedy drama series ''Orange Is the New Black'' (2013–2019), for which she won a Screen Actors Guild Award for her role as part of the en ...

as Schuller Gallery Artist * Naomi Scott as Seductive Woman at Gallery * Julie Lauren as Josh's Date *

Idina Menzel Idina Kim Menzel ( ; ; born May 30, 1971) is an American actress and singer. Particularly known for her work in musicals on the Broadway stage and having achieved mainstream success across stage, film and music, Menzel has garnered the honori ...

as Bridesmaid *

Vinny Vella Vincent Frank Vella (January 11, 1947 – February 20, 2019) was an American actor, talk show host and comedian. He acted in more than forty films often in the role of a gangster. He was best known for the role of Artie Piscano in Martin Scorses ...

as Cab Driver * Adele Reichman as Grandma Interrogating Helen * Hillel Friedman as Rabbi

Release

Festival screenings

The

film premiere A première, also spelled premiere, is the debut (first public presentation) of a play, film, dance, or musical composition. A work will often have many premières: a world première (the first time it is shown anywhere in the world), its first ...

d at the

Los Angeles Film Festival The LA Film Festival was an annual film festival that was held in Los Angeles, California, and usually took place in June. It showcased independent, international, feature, documentary and short films, as well as web series, music videos, epis ...

on April 21, 2001,Kissing Jessica Stein
Side Reel
, Retrieved on March 17, 2008 receiving the Audience Award for Best Feature Film and a Critics' Special Jury Award. The film was next shown at the

Toronto International Film Festival The Toronto International Film Festival (TIFF, often stylized as tiff) is one of the largest publicly attended film festivals in the world, attracting over 480,000 people annually. Since its founding in 1976, TIFF has grown to become a perman ...

, with screenings scheduled the day before and the day after the

9/11 attacks The September 11 attacks, commonly known as 9/11, were four coordinated suicide terrorist attacks carried out by al-Qaeda against the United States on Tuesday, September 11, 2001. That morning, nineteen terrorists hijacked four commerci ...

. According to the

DVD commentary An audio commentary is an additional audio track, usually digital, consisting of a lecture or comments by one or more speakers, that plays in real time with a video. Commentaries can be serious or entertaining in nature, and can add informatio ...

track by Westfeldt and Juergensen, both screenings took place, with the second screening on September 12 producing audible gasps among audience members at the sight of the World Trade Center. The two filmmakers decided to eliminate the nine or ten scenes featuring the Twin Towers because they were not integral to the story and distracted from it.

Critical reception

The film was hailed by critics upon release. It withstood some criticism from the LGBT community for not dealing in depth with the difficulties of being openly gay, but even among these criticisms, it was praised for portraying a same-sex relationship in a positive light. The website

AfterEllen.com AfterEllen (also known as AfterEllen.com) is an American culture website founded in 2002, with a focus on entertainment, interviews, reviews, and news of interest to the lesbian and bisexual women's community. The site covers pop culture and lifes ...

, which tracks the portrayal of lesbian and bisexual women in the media, reviewed the film positively. On

Rotten Tomatoes Rotten Tomatoes is an American review-aggregation website for film and television. The company was launched in August 1998 by three undergraduate students at the University of California, Berkeley: Senh Duong, Patrick Y. Lee, and Stephen Wan ...

, the film has an 83% "fresh" rating based on 120 reviews, with an average rating of 7.01/10. '' The Advocate'' magazine listed the film as an essential film for LGBT viewers, stating that "By no means is it a model lesbian movie — in fact, the film is a more honest look at bisexuality and sexual fluidity — but it is certainly a movie that encourages exploration and self-awareness." In the book ''Sexual Fluidity: Understanding Women's Love and Desire'',

Lisa M. Diamond Lisa M. Diamond is an American psychologist and feminist. She is a professor of developmental psychology, health psychology and gender studies at the University of Utah. Her research focuses on sexual orientation development, sexual identity, and ...

cites the film as a notable example of female sexual fluidity in popular culture, writing that it "depicts a lesbian becoming involved with a man, contrary to the more widespread depictions of heterosexual women becoming involved in same-sex relationships."

References

External links

* * * * * {{DEFAULTSORT:Kissing Jessica Stein 2001 films 2001 independent films 2001 LGBT-related films 2001 romantic comedy-drama films American LGBT-related films American romantic comedy-drama films Female bisexuality in film 2000s English-language films Films scored by Marcelo Zarvos Films about LGBT and Judaism American films based on plays Films directed by Charles Herman-Wurmfeld Films set in Manhattan Films set in Westchester County, New York Films shot in Connecticut Films shot in New York (state) Fox Searchlight Pictures films Impact of the September 11 attacks on cinema American independent films Lesbian-related films LGBT-related romantic comedy-drama films 2001 comedy films 2001 drama films 2000s American films