Hannah is feeling down, and Marty has just been dumped, so the two of them decide to go out together, both to celebrate her birthday and to mark the end of his relationship with Alice – but they both insist it's "not a date".

Marty is in turmoil when his mother stops by for a visit and Hannah gets him face his relationship with her, so he can get rid of all the angst it generates.

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

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.

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 decides to quit teaching and leave her boyfriend, Jack, to return home to Chicago and pursue a career as 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 opening at Chicago Monthly, the magazine where he works as a writer. Hannah goes to 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?" by 9 o'clock the following morning.