Kissing Jessica Stein is a good example of an independent film using its strengths in writing to make up for the fact there was little money. An independent film isn't going to have much in the way of production values. That puts even greater pressure on the script.
Some indie writers make up for no money with a gimmicky premise, like Memento or Run Lola Run. Others turn their weak production values into their greatest strength, like The Blair Witch Project. The writers of Kissing Jessica Stein use a cute, but eye-catching premise and good scene and dialogue writing.
This film - about a woman who tries going out with another woman after the hetero dating scene becomes intolerable - uses a similar technique to the one Sex, Lies and Videotape used many years ago. It promises sexual titillation to get you into the theater, but never delivers on it. Normally this is very dangerous. You better deliver the promise of the premise or the audience will think their investment was wasted.
But here the writers deliver so many funny scenes and lines of dialogue that you don't mind the prudery of the film itself. This kind of light, fluffy writing is much more difficult than it may appear. Romantic comedy is the soufflé of genres. You've got to be very good to make it appear effortless, and that especially means being good at witty repartee.
These writers are. Luckily they are also good enough actresses to play what they have written. And they are helped immeasurably by the terrific actresses playing the mother and the best friend.
This film has a conventional structure. But it is a great example of the most important rule of genre films in Hollywood, which is hit all the beats of the genre but do them in an original way to make it fresh.
The biggest structural problem this film has is the way it sets up the male love interest. The writers make him so unappealing at the beginning they can never bring him back. That results in a weak ending where we're supposed to believe the hero will eventually find happiness with the guy.
You can see why the writers made this choice. They had to shut down the possibility of the hero going with a man in the beginning so she will be forced to date women. But the writers don't just get rid of the guy. They blow him up with nuclear toxicity. Those are the kinds of writing choices you have to watch out for because of the terrible consequences you inevitably pay at the end.
But in a script whose strengths are scenes and dialogue, this isn't a lethal blow for the movie as a whole.
