Jessica is smart and successful with a loving, tight-knit family, but she just can’t seem to find the right guy.  She tries, but all the men she goes out with are duds.  Her boss, and ex-boyfriend from college, Josh, lays the blame at her feet, saying she is critical and picky.   Like magic, the right person appears through an ad in the relationship classifieds.  Smart, interesting, with a quote from Jessica’s favorite book.  It’s fate.  It’s a match made in heaven.  Except the person in the ad is a lesbian and Jessica is straight.

After another miserable date, Jessica can’t help herself.  She answers the ad and meets Helen, but doubts herself from the first moment.  The two inexplicably move forward in their relationship as Jessica flits around like a frantic bird, wanting one thing, saying another, changing her mind from one second to the next and over analyzing her emotions and reactions.  Helen really likes her, and honestly has the patience of a saint as she waits for Helen to break through her reservations in having sex with another woman.  The movie does end happily, although probably not the way some would anticipate.  Helen is the catalyst for Jessica’s awakening.  She is able to return to her art, take risks to express herself emotionally.  She’s still neurotic, but has become someone who is open, intimate, and able to create.

The movie really trades on the whole New York City/big city lifestyle, with lots of shots of both Manhattan and Upper West Side neighborhoods.  Yes, there is the stereotypical Jewish mother, and gay friends, but the portrayals are well rounded and engaging.  I really liked the clips of Jessica on her unsuccessful dates – especially the date who described himself as “self-defecating