The movie opens with Ryden Malby (Alexis Bledel) preparing for her college graduation. Ryden has had her life planned out since she was eleven. She wanted to get good grades, earn a college scholarship and get a great job at the publishing house Happerman and Browning. So far, everything is on track including the interview she has scheduled for her dream job.
At the graduation ceremony, Ryden's family arrived late, causing a little bit of a scene. In addition to her parents (Jane Lynch and Michael Keaton) and little brother, her grandmother (Carol Burnett) is there with her oxygen tank. Ryden's rival, Jessica Bard, gives the graduation speech and then Ryden and her family go out to eat to celebrate. Ryden's best friend, Adam (Zach Gilford) joins them. Adam has had feelings for Ryden since they met freshman year. He has also applied to law school at Columbia, but has not decided if he wants to go if accepted. Meanwhile, Ryden reveals to her family that she has an interview scheduled the next week and that she's even found a loft apartment that she plans to rent.
Adam goes with Ryden to look at the apartment before her interview. She is so confident of her prospects that she leaves an application and hefty deposit check. On the way to the interview, a truck hits Ryden's car and drives away without giving her his insurance information. Ryden is forced to hustle to Happerman and Browning.
When she arrives for the interview, she is directed to a waiting area filled with other applicants. Finally, it is Ryden's turn to interview. When asked why she wants the job, she gives an eloquent speech about how she's been preparing for it her whole life and she can't imagine herself doing anything else. The interviewer responds with a blank stare and thanks her for coming. As Ryden is leaving, Jessica Bard arrives and the interview greets her warmly.
Unemployed, Ryden gives up her dream of living in the loft apartment and moves in with her parents. Ryden's father insists that he can fix her car himself, despite her protests. As they unload the truck, her father steps in poop left by the neighbor's cat. He confronts the neighbor, David Santiago (Rodrigo Santoro). Adam watches as Ryden meets, and is clearly attracted to, David.
Ryden proceeds to interview for a number of jobs without success. Her father accidentally runs over David's cat. Ryden and David get to know each other. He offers her a job as a production assistant on the infomercials that he directs and they start to get physical when her family walks in, interrupting the moment.
Ryden has a number of run-ins with Jessica Bard, who got the job at Happerman and Browning. Meanwhile, Adam has not decided if he should go to Columbia Law or pursue music. He gets the opportunity to headline at a local venue and plans a big night with a fancy celebration dinner with Ryden. However, Ryden ends up spending the evening with David and forgets about her plans with Adam. When she arrives home, Adam is waiting for her. He tells her that he's tired of waiting for her to love him the way he loves her and he doesn't want her to be a part of his future.
Eventually, Ryden gets a call from Happerman and Browning offering her the job. Jessica has been fired. Ryden proceeds to work long hours doing menial tasks. She tries several times to call Adam to apologize, but he won't take her calls. Finally, in a grad gesture, she borrows an ice cream truck and drives it to where he's playing basketball. She reminds him of his advice to her earlier that any problem can be solved with an eskimo pie. He tells her that he forgives her, but he can't hang out with her because he's leaving for New York the next day. He says he'll call when he settled and goes back to his game.
Ryden finally realizes who she spends her life with is more important than what she's doing, so she packs her things and flies to New York to surprise Adam and tell him that she loves him.
In the final scene, the Malbys call Ryden to tell her that they are all coming to visit.
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