Tina Fey plays Portia Nathan who has worked as an Admission Officer for Princeton University for more than 15 years. She is in a long-term mundane relationship with her boyfriend who is a professor. Their relationship whiloe comfortable, has no spark. He treats her like a beloved pet dog, patting her on the head when they are ready to go to sleep. Her life is routine, predictable, and extremely boring. The boss of the Admission's Department, Clarence (played by Wallace Shawn) tells his staff that he is retiring at the end of the year. He then tells Portia and her co-worker Corinne (played by Gloria Reuben) that the position will be given to one of the two of them when he retires. This sets up a rivalry between the two women as they fight for the job. While under this pressure, Portia's boyfriend leaves her for another women which devastates her, as it was the last thing she expected from her normal boring life.
Portia's job is to recruit the top high school students for admission to Princeton which has become even more important as Princeton has fallen from the #1 school in the country to #2 for the first time in decades. As part of her job, she travels to high schools to tell them about the secret of getting into Princeton, when more than twenty thousand applicants come in each year and only about one thousand are accepted. She tells the prospective applicants to "Be yourselves", knowing full well that if they are themselves that will be the reason they will be rejected.
Portia gets a telephone call from a teacher John Pressman (played by Paul Rudd) who has an experimental school called Quest. He invites her to meet the kids from his school. Portia agrees to visit the school. To her surprise when she goes there, the students have little interest in attending Princeton which they think is not very important. All except one, Jeremiah Balakian (played by Nat Wolff) who is a self-taught genius but had trouble getting good grades in school. Jeremiah wants to go to Princeton.
John tells Portia that Jeremiah is her son that she gave up many years before for adoption and has a birth certificate to prove it. Portia struggles with the news, stays with her mother who lives nearby to try to figure out what to do. Her mother Susannah (played by Lily Tomlin) had Portia out of wedlock from having sex on a train with a man she just met and didn't even get his name, so Portia knows nothing of her father. This makes Portia even more guilty about what she did by giving up her son for adoption. While learning more about her son, Portia falls for John in a big way.
Jeremiah's dream is to go to Princeton, but he just doesn't make the cut. Portia risks her job by changing his status, which is discovered by her boss and she is fired because of it. When Portia finally gets up the nerve to tell Jeremiah that he is her son, she is shocked by the outcome.
Best part of story, including ending:
I like the alternative high school, how all the students can think for themselves, and most reject the idea of Princeton being so immensely important. This contradiction of every other school's reaction of wanting desperately to figure out how to get accepted at Princeton is very interesting.
Best scene in story:
A funny scene is when John takes Portia home and they kiss by accident. Then they get out of the car and Portia's mother hears her tell John no. When Portia's mother comes outside with a rifle and fires it in the air saying "No, means no!" it is hilarious.
Opinion about the main character:
Portia is a milk toast, that has taken the comfortable way in life but has never really tried very hard to excel. All she does is judge all the student applicants for Princeton, but when she is forced to take a very hard look at herself, she doesn't like what she sees.