Jessica Stein is a sensitive but neurotic New York reporter– she is at completion of her emotional rope. Her bro’s engaged, her friend’s pregnant, she hasn’t dated in a year, and she can’t sleep. After a nightmarish but optimistic dating spree, she discovers an interesting individual ad, whose just drawback is that it’s in the ‘ladies looking for ladies’ section. On a daring whim, she decides to address it. She fulfills cool downtown hipster Helen Cooper for beverages and, to her surprise, they click quickly. Their night of banter, connection and heated dispute culminates in a kiss that confuses and intrigues even the hesitant Jessica.
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With standard gender roles absent, the 2 females continue to muddle through an earnest, however funny courtship, making up the rules as they go along. Jessica doesn’t truly know ways to analyze this new situation. Everyone at Jessica’s office notice that she is strolling on cloud 9 and is really pleased. Josh– her employer (whom she dated for a while in college) also notifications and begins to feel strange that he’s not a part of this new, better Jessica.
This tension blows up 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 shop, trying a gown for her bro’s wedding event. Helen passes by, sees Jessica in the dress and asks her exactly what it’s for. Her mom is surprised that Helen didn’t understand about the wedding and is much more shocked when Helen stated she didn’t get the invitation. Helen lacks the store, Jessica follows and the two have an argument about it outside. Jessica declines to bring Helen to the wedding with her and Helen gets upset and tells Jessica that it’s over.
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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 states really much– till her mother states, “Jessica, I believe Helen is a really great girl.” Jessica hurries to Helen’s apartment and invites her to the wedding. Helen goes and concurs.
At the wedding, all of the grannies in participation are asking Jessica and Helen about their relationship and are totally encouraging– as well as nosy. Jessica and Helen look happy. Josh is late to the wedding, so is still entirely in the dark about the relationship. That night, Josh informs Jessica that he is still in love with her. She comes out to him and he’s completely surprised.
Time goes by, and Jessica and Helen go from being lovers to being simply friends. That is insufficient for Helen so she vacates. Jessica is crushed but gets over it. She and Helen continue to be finest good friends. Jessica also faces Josh (they both quit their jobs) in a book store and the 2 pledge to satisfy up.
The last scene of the film is of Jessica meeting Helen for beverages, after Jessica had her “very first date” with Josh.
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