Synopsis
Sarah Michelle Gellar stars as Brett Eisenberg, an ambitious yet unconfident young New York assistant book editor living in the literary hotbed of Manhattan's Upper East Side. Struggling to become a full-fledged editor, a task made harder after her mentor and boss is fired and replaced by Faye Falkner (Vanessa Branch), Brett meets the notorious and much older publishing playboy Archie Knox (Alec Baldwin). After spending time with him she realises how unhappy she is with her immature boyfriend Jed (Chris Carmack) and breaks off their relationship in order to pursue one with Archie.
Archie is revealed to have several issues such as being an alcoholic, although he is almost three years sober; suffering from diabetes; and having an estranged daughter. The age-gap between Brett and him is made clear through their different lifestyles, such as his lack of understanding how to use a Blackberry and Brett taking him to a candy shop. Although this does not affect their relationship in the beginning - Brett appreciates the advice and confidence he gives her to stand up to her boss - she soon begins to resent his patronizing attitude. He eventually begins drinking again and sleeps with another woman in order to break off their relationship.
At the same time, Brett is shown to be incredibly close to her father; she is seen constantly explaining her situation and asking for his advice. While visiting her family home she is shocked to discover that he has cancer and that she was the last to know behind her brother Ethan (Ebon Moss-Bachrach), because her father felt she could not handle the news. Feeling depressed and unwell, Brett makes an awful impression on a celebrity client until Archie appears and rescues the situation. They decide to give their relationship another try and Brett introduces him to her family, who are uneasy with the age difference; her father especially after learning that Archie is an alcoholic when he is admitted to hospital. Brett's father tells her that she shouldn't have to spend her life taking care of Archie.
Later, it is revealed that her father has died and Brett realizes she must finally deal with her problems without his support. Following this, Archie proposes using the Blackberry Brett bought him but she turns him down, telling him that they see each other as teacher and student and not as equals. She says she needs time to be happy and grow up on her own.
The end of the film finds Brett finally confident in herself as she finally wears a pair of leather pants she was previously too scared to wear, and editing her work in a decisive way by using a pen instead of a pencil, as is seen throughout the film.
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