Wine Country Abby (Amy Poehler) decides to celebrate her friend Rebecca’s (Rachel Dratch) 50th birthday with a weekend getaway over Rebecca’s protests that she wants a low-key celebration. Abby, Rebecca and four of their friends, whom they have known since they were young waitresses, decide to spend the weekend together in Napa.
Rather than allow the women to relax and drink Abby wants them
to adhere to a strict schedule, a way of seizing control as, unbeknownst
to the rest of her friends, she has recently lost her job. All the other friends
are struggling with problems of their own: Rebecca is in denial that her
husband is inattentive and her friends hate him, Naomi (Maya Rudolph)
is afraid of receiving test results from her doctor, successful business woman
Catherine (Ana Gasteyer) feels that the rest of the friends are cutting her out,
Val (Paula Pell) is looking for love and Jenny (Emily Spivey) a depressive writer,
is simply miserable in life.
On Friday the friends eat at an expensive restaurant where Val flirts with their waitress, Jade.
The following morning the women have a sinister tarot reading from a woman called Lady Sunshine. Afterwards they go day drinking around Napa. Near the end of their tour there is tension when Abby snaps at the other women for not adhering to their schedule. When Rebecca goes to talk to her about her attitude Abby reveals that she lost her job. In anger Abby throws out her schedule and the women decide to go to Jade’s art gallery opening.
They are shocked that Jade’s art is all related to The Nanny. During a Q&A
Abby rants on how younger generations have it too easy but ends her speech
by saying that they are Fran Fine (in reference to Fran Drescher’s character
on the show The Nanny) causing the art goers to believe she is a part of the exhibit.
Val stays behind to flirt with Jade but when she tries to ask her out Jade assumes she is trying to buy a painting and humiliated, Val agrees to buy it.
Returning home drunk and miserable Abby is propositioned by Devon the housekeeper (Jason Schwartzman) and has sex with him.
The next morning Naomi goes to wish Rebecca a happy birthday and finds
her on the floor having thrown out her back. Rebecca reveals that spending
the night on the floor led to the epiphany that she hates her life. She agrees
to adhere to Abby’s schedule and all the women, except Catherine who they
can’t find, go to brunch. Catherine eventually arrives and accuses the other
women of trying to cut her out. Naomi tells her she is locked in a self-fulfilling
prophecy as work means she has no time for her friends and not spending more
time with her friends makes her work harder. Naomi then reveals she also has
problems as she is waiting on the results of a BRCA1 and BRCA2 test and then
storms out of the restaurant. After Rebecca tells Abby that the birthday weekend
is more for her than for Rebecca, Abby storms out as well.
Naomi and Abby are pursued by the rest of the women in a golf cart. Naomi is bitten on the ankle by a snake and as they can’t get cell phone reception Val decides to run down the side of the steep hill they are on to get help. One by one the other women follow Val down the side of the hill. Catherine is the last one to go and gives an emotional speech at the top of the hill about why she is planning to turn down a lucrative job opportunity to spend more time with her friends, a speech that they don’t hear.
Arriving at the hospital, they learn that Naomi is fine. Catherine also calls the doctor for her and learns Naomi’s blood tests came back negative.
That night, the women sit around drinking and invite the lonely local owner of the house they are staying in, Tammy (Tina Fey), to join them.