Director: Charles Herman-Wurmfeld
Written, Co-produced, and Starring: Heather Juergensen and Jennifer Westfeldt
Producers: Eden H. Wurmfeld and Brad Zions
Running Time: 97 minutes
MPAA Rating: R for Sexual Content and Language

Plot Summary: Jessica Stein, an attractive, intelligent, semi-neurotic perfectionist in her early thirties, is at the end of her dating rope. One of her best friends is having a baby and her brother is getting married. After a string of dates that could only be construed as anything but promising, Jessica is desperate. One day in the office, her co-worker comes across a personal quoting Jessica's favorite poet/author, Rainer Maria Rilke. Intrigued, she asks more about the mystery man only to find out that her mystery man is, in fact, a woman. Regardless of this not-so-small flaw, Jessica responds anyway. Thus ensues a witty and well-written outlook on dating and gender roles.

*****SPOILERS*****

Regardless of how funny I thought this movie was, I didn't like the ending the first time I saw it. I didn't hate it, but I wanted Jessica and Helen to stay together at the end, but then I started thinking about it some more. A lot of heterosexual people experiment. Jessica needed Helen and Helen needed Jessica at this exact time to, in a sense, help sort out the chaotic world in which they lived. Helen helped Jessica to not be so neurotic - to not live inside the box. At one point, Jessica says to Helen, while discussing lesbianism: "In the past whenever I've thought of lesbianism, I just thought 'ew, ew, can't go there, can't get excited'. You know, what would we do?" But then Helen opens all these new doors for Jessica, making her more confident. In the end, Jessica quits her job to paint, something she had talent for, but gave up during college.

But vice-versa. Jessica helped Helen as well. Before Jessica, Helen dated three guys. One of them she called up when she was horny, one when she was hungry, and one was she was bored. The two different perspectives is even illustrated in their choice of lipstick. Jessica prefers to use one and Helen blends, using three different types. After Helen and Jessica break up, Helen is with another woman. Now, you may think what I did - that she was just bisexual, but I think it took Jessica for Helen to realize she only needed one person to make her happy and that was another woman, not three different men.

Overall, if you don't like the ending, I think it's worth the watch just for the humor value. One of my favorite scenes is when Jessica and Helen first meet and they talk about yoga and exercise. (note: this is not word for word, I'm just doing it from memory, but you'll get the gist)
Jessica: Oh I could never do yoga. I can't do the whole sitting still and breathing thing.
Helen: So what do you do for exercise?
Jessica: The usual. Walking. Running. I have to keep moving otherwise I'd panic.
Helen: What do you do when you sleep?
Jessica: Oh I'm a terrible insomniac.
Helen: Aww, since when?
Jessica: Um, since birth.

From imdb.com:
Jennifer Westfeldt .... Jessica Stein
Tovah Feldshuh .... Judy Stein
Esther Wurmfeld .... Grandma Esther
Hillel Friedman .... Rabbi
Ben Feldman .... Himself
Robert Ari .... Sidney Stein
David Aaron Baker .... Dan Stein
Jennifer Carta .... Rachel, Dan's Fiancee
Ben Weber .... Larry
Brian Stepanek .... Peter
Nick Corley .... Howard
Jackie Hoffman .... Joan
John Cariani .... Chuck
Scott Cohen .... Josh Myers
Christopher Berger .... Malaprops Guy
Hayden Adams .... Weird Smooth Guy
Kevin Sussman .... Calculator Guy
JM J. Bullock .... Not-Yet-Out Gay Guy (as Jim J. Bullock)
Heather Juergensen .... Helen Cooper
Alysia Reiner .... Schuller Gallery Artist
Carson Elrod .... Sebastian
Michael Mastro .... Martin
Tibor Feldman .... Roland
Michael Showalter .... Stephen
Michael Ealy .... Greg
Naomi Sablan .... Seductive Woman at Gallery
Jon Hamm .... Charles
Allen Fitzpatrick .... Matthew
Julie Lauren .... Josh's Date
Jimmy Palumbo .... Cheesy Pick-up Guy #1
Thomas L. Bolster .... Cheesy Pick-up Guy #2 (as Thomas Bolster)
Vinny Vella .... Cab Driver (as Vinnie Vella)
Peter Hirsch .... Stanley
Idina Menzel .... Bridesmaid
Adele Reichman .... Grandma Interrogating Helen
Amy Wilson .... Bookstore Saleswoman
Ilana Levine .... Laurie, Helen's New Girlfriend

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