What was Jessica looking for?

I think Jessica was looking for someone that she clicked with, and it turned out to be a woman. That created a lot of consternation for her, given the sexual implications of that, and her own self-perceptions of herself as a straight hetero woman. There is a theme of "never being satisfied" or "never being good enough" that creeps through the film, and Helen seems to be good enough except for the fact that she's a woman.

I think the film rates very poorly in trying to explain exactly why the relationship failed. It makes me think that this feature was not a part of the original script, perhaps. We are given clues ... Helen wants more sex, Jessica says Helen wanted someone who was "more gay". Perhaps these clues add up to a realization on Jessica's part that although she loved Helen she was less than fully engaged with the lesbian sex, and that this made Jessica and Helen incompatible, eventually. Perhaps, but the movie doesn't really say that. Instead, when Jessica is discussing the relationship with her pregnant friend, she describes the sex as great ... so it's a bit of a puzzle as to why, precisely, this seemingly good relationship goes bad. All we know is that, as far as the film is concerned, it goes bad suddenly and shockingly, and without too much explanation. It's possible that Jessica wasn't comfortable with her sexuality (but we don't know this because, unlike what we are told about Helen, the film doesn't really tell us what Jessica's conclusions are about her own sexuality), but it's also possible that Jessica was just not as sexual a person in general as Helen, and that on this level they were sexually incompatible -- not because the sex was lesbian but because their general sexual appetites were very different. But the film doesn't tell us any of this, and as a result I think that is a flaw in an otherwise entertaining film.

I dont see Jessica as a "free-spirit"
Even her own mother saw that her "prefectionism" would ruin her life.
Every character saw it, except Jessica.
She really didn't have that much insight into her attitude toward new things (read: fear), but she was able to know that happiness was missing in her life.

That she momentarilly delved into lesbianism, I dont believe that Jessica was using lesbianism as some kind of frivolous "experiment"; I do not believe that Jessica was that shallow.

I believe she was honestly drawn to Helen, perhaps not because Jessica was actually a lesbian, but because she was so lonely and out of touch with her own needs, that Helen was exactly what she needed: someone unexpected.

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The movie doesn't just show Jessica's story. It shows the story of two women who were both trying something new. The reason things didn't work out was because Jessica wasn't gay. She found many things through the relationship though. From the beginning you could tell she couldn't really talk to anyone. Jessica rekindled her passion for art and she had a close relationship with someone. That is what brought her happiness. She was doing what she loved and was able to really talk to someone. Helen on the other hand ended up being gay. It just showed both sides and what each woman learned about herself through it.

I disagree with you there, that someone is straight or gay, no inbetweens. I know several bisexual people, they just happen to be attracted to both sexes. I really don't think that there are any extremes. I think that whether you are straight or gay, everyone has at least had a thought about someone of the same sex. It's perfectly normal. Most people tend to lean toward one side though. I'm a primarily gay woman, but I've been attracted to men before. Not often, and not all men, but there have been a few. I don't really consider myself Bisexual, because my attraction to men and women is no where near equal. I think that's how Jessica is, only the opposite. She likes men, but she was also attracted to Helen. She wasn't attracted to all women, just Helen, and it was normal for her.

I also have been reading all the messages on this board and I am very impressed; everyone has her/his own reasonable point. At first, I also disappointed by the fact that Jessica and Helen didn’t end up together. Well…that’s because I always believe that most women are straight until they are not! But, the end just confused me a little bit. So I try to make my own interpretation to confirm my belief and the followings are what I come up with. First, as it has been foreshadowed, Jessica is not a free-spirit person; she was framed by social expectations: to be perfect is to be normal (straight), to contribute something to society (as a journalist), to have goals in everything she does. She “never plays it by ears” as Helen does. She is what she thinks she should be not what she really wants to be. Being a lesbian is something unexpected and that makes her feels guilty and insecure. In the scenes when she unexpectedly met the pregnant friend in front of the grocery store and then when she made the confession, she was totally freak out. Though her friend and family were very supportive, it was she herself who couldn’t accept it. Does anyone remember the scene when Helen successfully turned Jessica on and one of her boyfriends came interrupting their action. The soundtrack of that scene is called Mad…I think it implies what Jessica thought about what she is doing and that is so NOT her- it is a phase of madness. That’s why she was happy to leave. Second, with all my respect but does it has something to do with being Jewish? Well, I am a Buddhist and I know very little about Judaism also I have never been to any Seder! Could anybody tell me how being lesbian may relate to being Jewish since Jessica seems to be a bit religious…is it some kind of ironic stuff? In brief, I think the ending is what “normal” people want to see… well… Josh and Jess. However, the message, for me, is not that people should “get back on track” being straight but it is that different kind of person make different choices; Jessica is more happy to live with her idea of being perfect while Helen live with her passion. And like corinnethewise has pointed out: the film is not that narrow since Helen is still with a women at the end.
I hope that makes sense for others.

I think the answer is pretty simple - Jessica was looking for the fictional "perfect" guy. She had dug herself into a rut in that pursuit, which has a wonderful metaphor in her flippant rejection that the Hare Krishnas are seeking nothing higher than "nicer robes". She's so quick to find fault with everything without looking deeper, that she's completely incapable of finding love.

Then the singles ad... Jessica finally sees a glimpse of the perfect person, only it's a woman. However, this glimpse of perfection is enough to encourage her to make a leap out of her rut. She meets Helen, finds a soul mate, and rides off into the sunset...

Well, not exactly. Jessica is straight: not a lesbian, not bisexual, not even really bi-curious. She's found a big part of what she's looking for in a mate, but it's not complete. She only gives in to the physical part of the relationship after she's made an investment in it, by introducing the mysterious Helen to her family. When her family later finds out the nature of her relationship to Helen, she feels a commitment to it (I mean, who would go through the embarrassment of "coming out" and then turn around and say "oh I guess I wasn't gay after all" without a struggle to keep the relationship alive to validate their coming out?)

Jessica and Helen's love relationship is doomed from the start, since Jessica is not gay. However, in the process, Jessica expands her horizons, and is enabled to discard the "perfect guy" blinders that have folded in over eyes, and realize that her love was already there, behind the editor's desk. Love took a circuitous route, but led to happiness in the end.

I think Jessica wanted to be loved...I don't think it occurred to her that she might find love with a woman, but Jessica yearned for love and affection and Helen was the first person to come to her with that full throttle.