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Jessica Stein is a sensitive but neurotic New York journalist – she is at the end of her emotional rope. Her brother’s engaged, her best friend’s pregnant, she hasn’t dated in a year, and she can’t sleep. After an optimistic but nightmarish dating spree, she happens upon an intriguing personal ad, whose only drawback is that it’s in the ‘women seeking women’ section. On a daring whim, she decides to answer it. She meets funky downtown hipster Helen Cooper for drinks and, to her surprise, they click instantly. Their evening of banter, connection and heated debate culminates in a kiss that confounds and intrigues even the reluctant Jessica.

With conventional gender roles absent, the two women proceed to muddle through an earnest, but hilarious courtship, making up the rules as they go along. Jessica doesn’t really know how to think through this new situation. Meanwhile, everyone at Jessica’s office notice that she is walking on cloud nine and is very happy. Josh – her boss (whom she dated for a while in college) also notices and starts to feel strange that he’s not a part of this new, happier Jessica.

This tension explodes one day, when Jessica is with her mother (who’s been setting her up with unsuitable men as far back as she can remember) at the bridal store, trying out a dress for her brother’s wedding. Helen passes by, sees Jessica in the dress and asks her what it’s for. Her mother is surprised that Helen didn’t know about the wedding and is even more surprised when Helen said she didn’t get the invitation. Helen runs out of the store, Jessica follows and the two have an argument about it outside. Jessica refuses to bring Helen to the wedding with her and Helen gets upset and tells Jessica that it’s over.

At dinner that night, Jessica starts getting very upset and leaves the dinner table. Her mother follows her out and sees that Jessica is crying. Neither says very much – until her mother says, “Jessica, I think Helen is a very nice girl.” Jessica rushes to Helen’s apartment and invites her to the wedding. Helen agrees and goes.

At the wedding, all of the grandmothers in attendance are asking Jessica and Helen about their relationship and are completely supportive – and even nosy. Jessica and Helen look happy. Josh is late to the wedding, so is still completely in the dark about the relationship. That night, Josh tells Jessica that he is still in love with her. She comes out to him and he’s completely shocked.

Time goes by, and Jessica and Helen go from being lovers to being just friends. That is not enough for Helen so she moves out. Jessica is crushed but gets over it. In fact she and Helen continue to be best friends. Jessica also runs into Josh (they both quit their jobs) in a book store and the two promise to meet up.

The last scene of the movie is of Jessica meeting Helen for drinks, after Jessica had her “first date” with Josh.


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