How do you get your dream job? You run after it, you fall, you get up and chase it again... Almost like you dream man. Lane (Hilary Duff) is a young and pretty great looking freelancer who is looking to get herself in the Cosmopolitan- the ultimate dream in the writing for magazine life. The only problem is, she needs to find a story good enough that will knock them off of their feet and making them want her. One of her friends, who actually works at Cosmo, gets her the chance to talk with Cosmo exec (Jaime Pressley). At first, she was horrible, but as two of them start chatting, they get to the idea of Lane working undercover in another company in order to find out a dream man that will fulfil all of her terms from the "check-list". And so, the adventure begins. Of course, Lane gets into the new company and after a while starts falling for her boss, Tom (Michael McMillan), who is totally opposite of everything she wrote down that she wants in a man. After couple of hours, she meets an English musician Liam (Chris Carmack), who sweeps her off of her feet with every thing in her check-list done. But, it turns out that he was a phony and she is back to square one. And her report awaits as well.