Two men approach two women sitting together at a bar. It doesn’t take long for the conversation to turn into discussing the appeal of lesbians. Soon, it is discovered the men don’t know the first thing about what happens when two women have sex.

This is the scene that sets Kissing Jessica Stein apart from other widely released independent films that deal with the ever-controversial issue of lesbianism. It is different – as well as hilarious – because we know that one of the women is just as clueless as the guys.

Kissing Jessica Stein is obviously not a Hollywood film – everything from its saucy subject to its inept sound design suggest as much – yet it plays by the rules of the familiar romantic comedy enough to make a mainstream splash.

We like Jessica (Jennifer Westfeldt) because despite all her faults – picky, anal, boring, unhappy – we see that she is desperately searching for something more. She thinks she finds it when she comes across a personals ad in the “woman seeking woman” section of the weekly tabloid.

Helen (Heather Juergensen), the bisexual who waxes poetic in personals ads, is also searching for something – well, something more than her three different male sex partners who constantly show up unannounced.

The question here is: Can Jessica let go of her pre-conceived notions of lesbianism and have a good time? And if she can, will she have the guts to tell her over-bearing Jewish mother?

While the protagonist experiments with homosexuality the way an obsessive-compulsive recluse would experiment with going on an airplane, she isn’t too hopeless to make us forget why we are rooting for her in the first place.

The film isn’t about a straight woman switching teams as much as it’s about going to the extreme to discover where you belong.

Kissing Jessica Stein is enjoyable because while we can guess where this neurotic woman will eventually end up, we still want her to take us with her every step of the way.

However, the film suffers from unoriginality and stereotyping when it comes to the array of stock characters whom Jessica must interact with during her first-dates-from-hell montage. The sequence is rather funny – she meets half a dozen losers at the same booth in the same restaurant – but the pacing and overall setup of the scene suggest the beginning of every other sex comedy rather than the original, heart-warming film it ends up being.

Written by Westfeldt and Juergensen initially as a play called Lipschtick, Stein is the culmination of years’ worth of work and effort and it ultimately shows.

It’s rare when a movie about growing as a person and taking a chance on love can be interspersed with a seeming sex comedy about lesbians.

Kissing Jessica Stein is Rated R

Opens today