Henry's and Tess' declaration that they are ""engaged to be engaged"" leads Ian to play yet another prank on Henry -- this time by setting it up to look like Henry did it with Maddie.

Henry scoffs at Ian's story about a guy being hypnotized into believing he committed a crime he didn't, claiming it's ridiculous. Ian, however, professes to be a hypnotic expert, and swears it could definitely happen. In an effort to kill two birds with one stone, Maddie asks Ian to prove it to Henry by hypnotizing her into enjoying the taste of lobster, since her date promised to cook it for her, and she can't stand seafood. Ian proves it to Henry alright. But when Ian's hypnotic powers turn out greater than even he imagined, Jake and Tess fall under his spell too. Soon, Ian's diabolical attempts to play William Shakespeare with them render the situation more tragedy than comedy.

Pryce, a Yale student, wants to do an interview with Henry for the college's alumni mag. When Pryce sets his sights on Ian, his interview turns up some shocking secrets about where Ian was nearly twenty years ago. But Ian is caught in a lie, after which he confesses to the gang that where he was was in a mental institution.

It's Christmastime, and there's a need to be afraid. Jake plans to fulfill his New Year's resolution to call his father who deserted him when he was ten, while Maddie prepares for a blind date with one Dr. Eric Woolf that her father set up. Tess tries to get her friends together for a Christmas party, but they've all got plans. So instead she latches onto Ian's party -- even though he doesn't want her there. Once Tess arrives and sees what Ian calls a Christmas party, she isn't sure she wants to be there either. But at least she's in good company with Ian's eccentric collection of friends: Vince from the looney bin, who has a habit of introducing himself as the last name said in his presence; Phyllis, the maintenance transvestite; Goldy, the midget newsstand guy; and Lois Bickford, the washed-up stage actress who did Ed Sullivan several times -- and still couldn't get on his show. Since Ian's gang are too busy watching a Knicks game to bother having any Christmas spirit, Tess decides t

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

At a book signing, Ian meets an obsessed and insane fan, Rod Dubelko, who makes Ian look down to earth in comparison. When Rod learns Henry is Ian's editor, he gets jealous and wants to take Henry's place. Ian sees a little of himself in his stalker and takes a liking to him, but Henry tries to change Ian's mind when Rod confesses to cutting the power to the elevator in Henry's building -- trapping Tess in the process. After Ian tells Rod that the editing position is already filled, his number one fan has something else in mind...

Under Audrey's orders, Henry makes Ian do a round table discussion with Charlie Rose. Henry stops by a funeral home to check out the coffins, where he learns that Henry is freaked out by death. Ian disregards Henry's sensitivities and buys a coffin from the funeral home anyway. Upon getting it home -- where he plans to use it as a piece of living room furniture -- Ian discovers the funeral place accidentally sold him a coffin with a corpse in it. Ian calls them to come pick it up, but before they get there, he has to go to his interview, leaving Henry stuck caring for the dead body in the meantime.

Oh what a tangled web Ian weaves when he writes a secret admirer letter to Kit, a blonde he likes, and asks Jake to deliver it to her apartment for him. Kit catches Jake slipping it under her door, tracks him down, and the two get it on. Only afterwards does Jake learn that Kit was ""Ian's girl.""

Tess (who narrates the tale) attempts to fix up Ian and Maddie after becoming jealous that Ian and Henry are hanging around each other too much. But it's a match made in hell after Maddie tries to teach Ian how to dance for their first date.

Henry, Ian and Tess get mugged. Henry does what you might expect, but Ian head-butts the mugger and saves the day -- as well as Tess' purse. Henry soon feels sexually inadequate when he learns that Ian's heroics caused Tess to have an erotic dream about Ian. When Henry won't stop whining, Ian sets up an incident that's designed to make Henry look like a hero in Tess' eyes. Meanwhile, Maddie uses Jake as a decoy boyfriend to avoid being chatted up by bar patrons, but Jake winds up a better decoy than even she wanted.

Ian's first novel, Below Ground, finds its way onto the reading list in Maddie's contemporary literature class. Maddie is thrilled since she's already read it and it will save her time. Ian helps write Maddie's book report for her, but then is furious when her professor only gives her a ""B,"" claiming that she doesn't understand the author's intentions! Ian goes down to talk to the guy, Professor Tuttle, and get the grade changed to an ""A,"" but when Ian blasts the crooked, thick-headed teacher with the declaration that he wrote Below Ground -- as well as Maddie's paper -- Professor Tuttle does indeed change Maddie's grade. To an ""F."" When Ian tells Maddie that Tuttle flunked her, she becomes as enraged as he was when he saw the ""B."" To fix things, Ian comes up with the plan to have Henry meet with Tuttle and claim to be the real Ian Stark, so Tuttle will think Ian was an imposter. Meanwhile, when Jake's girlfriend, Kit, gives him a ""man necklace"" as a gift, which is so ugly and bulky he

While boxing with Jake on the balcony, Ian accidentally knocks a pigeon's nest filled with eggs off the ledge -- and doesn't care. But after hearing one too many of Jake's lectures about pigeon vengeance, when the mother returns to the balcony and seems to know who did it, Ian becomes more paranoid and fearful than Henry that it has come to get him. Worse, Ian's panic attack threatens a meeting Tess arranged with his favorite author, Terrance Sterling, when the pigeon refuses to go away. Meanwhile, Maddie receives somebody else's package containing an expensive cashmere sweater and likes it so much she doesn't want to give it to its rightful owner, while Henry gets seriously turned on when Tess tells him that she went to school with Terrance's lesbian daughter, Brooke, who had a crush on her.

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

Audrey and her flaming French partner, Cesar, throw an extravagant dinner party, and invite Henry and Tess with the sole purpose of getting them to bring Ian. Ian hates parties, so Henry has to beg Ian to do him and Audrey a favor and go anyway. But Tess gets food poisoning from bad sushi and has to cancel, leaving Henry with no choice but to bring Maddie as his date. Ian gets bored at the party -- where he is hounded by a phony 20th Century FOX executive, Danny Lukor -- and decides to spruce things up by taking one of Cesar's prized exotic fish and putting it in Henry's drinking glass. From there it's a comedy of errors as Henry, Maddie and Tess (who shows up still sick to her stomach) try to sneak the fish back into the tank without Cesar noticing.

When Ian plots a story featuring a couples counselor, he and Henry schedule an appointment with one to get the lowdown on how they operate. The couples counselor, Anne, gives Ian and Henry her analysis of them as a couple, and then speaks with Ian alone. When Henry asks Ian what Anne said to him, Ian says she thinks Henry is paranoid -- thus making Henry more paranoid. But when Henry learns that Ian was lying to him and Anne actually asked him out on a date, Henry plots his revenge. Meanwhile, Maddie tricks the new bartender, Scott, into believing she owns the bar -- and uses her powers for evil, not good.

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?

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.