Henry McNeely's boss, Audrey, gives him a promotion he doesn't want: that of editor for flavor-of-the-month horror novelist Ian Stark -- who keeps editors like Henry keeps his backbone. Ian's eccentricities and penchant for practical jokes and spontaneous daredevil stunts -- at the expense of not actually writing a follow-up book -- threaten Henry's anal-retentive, obsessive-compulsive and fraidy-cat ways. Can two single men share a job without driving each other crazy?

Ian's curiosity is piqued after Henry mentions picking up a gift for his girlfriend, Tess, for their anniversary. When Henry refuses to tell Ian anything more about her out of fear Ian will play a practical joke on her, Ian waits until after Henry calls Tess -- and then uses redial to find out where she is. Working in an art gallery is where. So Ian goes there, meets Tess, and pretends to be a couples counselor to trick her into giving him the juicy details about Henry. Ian soon learns to be careful what you wish for when he returns home, horrified, and tells Maddie and Jake that Henry's girlfriend thinks he's a dud in bed and secretely wants to be entertained with toys. Naughty, naughty toys. After Henry comes back with Tess' gift -- flannel sheets -- Ian comes clean about Tess' confession, while Henry figures out Ian hit redial. Henry begs Ian to give him kinky tips to please Tess, so a nauseated Ian takes Henry out to a sex shop that sells S&M toys. Then Henry drops by the art galle

Henry doesn't understand why Ian changed the name of a character in his manuscript from Lily to Renska, nor does he understand why Ian's favorite coffee shop is thirty blocks away. Wanting to understand Ian better, Henry pays a visit to Ian's coffee house of choice, where he discovers that Renska, the owners' daughter, is a waitress there -- whom Ian never talks to. Ian denies to Henry that he has a thing for Renska, but Henry doesn't believe him. Thanks to Henry's big mouth, Renska's over-protective parents thrust Ian into a date with their timid daughter the next time he stops by. Furious, Ian blows up at Henry because his morning routine of fritters and long walks has been ruined -- but Henry's attempt to correct the matter destroys Ian's routine even more. Meanwhile, Maddie has to fend off the unwanted advances of her pompous professor, Forrest St. James, when she sends Jake to her psychology class to take notes for her, and he ends up penning an overly flattering teacher evaluatio

Henry's germophobia kicks in as he struggles to maintain a ""five-foot perimeter"" from Ian, who's got a cold. But Henry catches it anyway. Audrey tells Henry that she's going to see her new client, Professor Huggles, the famous children's author whom Henry is enamored with. So Henry tags along to lunch with Audrey to meet him. Henry impresses Professor Huggles with his ability to recite lines from the author's best-known book, ""Kyle the Kite Learns to Smile at the Night,"" and the two share a hug. But the next day, Henry, Ian and Jake hear on the news that Huggles died from complications of a common cold. Ian torments Henry with accusations of hugging his childhood hero to death and infecting the five-foot perimeter. Overcome with guilt that he was responsible for Huggles' death, Henry begins having nightmares where Kyle the Kite beats him up. Ian finds these most amusing - until he begins having them, too. Henry decides to clear his conscience by going to Huggles' funeral and confessing

During Halloween, Ian helps Henry pay back his pregnant cousin Lori for a prank she pulled on him a long time ago, while Maddie's date -- who's dressed up as Igor -- may or may not be a humpback for real.