Plot Summary

At the center of this unconventional romantic comedy is Cristabel Abbott (Paris Hilton), a flawless “perfect ten,” her less fortunate best friend June Phigg (Christine Lakin), and Nate Cooper (Joel David Moore), who finds himself hopelessly caught between them.

Nate has been deeply in love with Cristabel since he first saw her at the age of six. Years pass, and despite dating other women, none can replace his idealized vision of Cristabel. Determined to reunite with his childhood crush, Nate returns to Los Angeles to find her once again.

He soon discovers that Cristabel is still single—and still stunning. However, there’s a catch: she refuses to go anywhere without her inseparable best friend June. Cristabel insists that June must also have a boyfriend so they can socialize as a group, making Nate’s romantic pursuit far more complicated than expected.

In an effort to get closer to Cristabel, Nate takes it upon himself to find a boyfriend for June. But June’s appearance and awkward demeanor make this mission nearly impossible. Realizing the challenge, Nate comes up with a bold idea—he decides to help transform June through makeovers and confidence-building.

As June gradually emerges from her shell, revealing her warmth and inner beauty, Nate begins to see her in a completely different light. In the process, he realizes that his long-held fantasy about Cristabel was merely an illusion—and that true love lies where he least expected it.