Ben (Seth Rogen) has been living for years off a $14,000 settlement check he received after a postal truck ran over his foot. He shares a house with some friends. Together they work on a website devoted to cataloging all the nude shots of celebrities (they think this is something novel.). They figure one day it will pay off. Alison (Katherine Heigl), on the other hand, is a hard-working assistant on an entertainment show. She lives in the guest house of her well to do sister and brother-in-law, and has her career arc all planned out. When she finally gets a promotion to become an on-air personality, she goes out to celebrate. That's when fate pulls a little joke and puts her together with Ben. The two have some drinks, get plastered, end up in bed and have a condom malfunction. In the morning, when Alison sobers up, she quickly dispenses with Ben and sends him on his way. Ben, who seems to consider himself lucky to have gotten as far as he did, doesn't seem to harbor any bad feelings about the chance encounter.