Hannah decides to quit teaching and leave her boyfriend, Jack, and return home to Chicago to become a writer. On the flight home to Chicago, Hannah meets and helps Marty deal with his fear of flying and he tells her about a research job open at Chicago Monthly, the magazine where he is a writer. Hannah goes down the magazine to apply for the job, meets the editor and is challenged to write a 2,000 word article on ""the tortilla wars, does Chicago prefer corn or flour?"" for 9 o'clock the following morning.

Hannah's first deadline prompts her first fight with Marty when she loses his article in the computer and he doesn't have a backup, much to Pamela's delight.

Hannah's old boyfriend and Marty's ex-college roommate are one in the same person, and Jack tries to convince her that he has changed. Meanwhile, Hannah and Marty are working on a story that will expose a charity scam.

Marty doesn't want anyone to know he is living in fear when he receives his first death threat.

Hannah is down in the dumps and Marty gets dumped, so the two of them go out together, for her birthday and the end of his relationship with Alice- but it's ""not a date"".