Martin Tupper, a New York book editor, is in the middle of a life-crisis: his soon to be ex-wife, Judith, is in a hurry to get divorce papers signed so that she can quickly remarry. Martin must decide if he wants to try to win her back or let her go and return to the dating scene.
Martin winds up in the hospital after hooking up with a much younger college girl. His doctor orders him to make some lifestyle changes in order to avoid another more serious incident, including avoiding caffeine.
Jeremy begins to fall behind at school when he is distracted by his attractive teacher. His teacher tells Judith about the issues and Judith insists that Martin give Jeremy "the talk." However, when Martin goes to the classroom himself, he too becomes distracted by the attractive teacher.
Martin's sister, Susan, arrives for a surprise visit and he asks Eddie to show Susan around New York. However, Martin is unaware the Eddie and Susan have been dating for nearly eight years.
While eating out, Martin and Eddie are surprised when their waitress is an old high school friend. They all discuss their lives since school and where they thought they would be by now. Inspired by the reminiscing, Martin decides to chase his dream and begin writing again.
Martin goes to a taping of the "Eddie Charles Show" with a guest author who speaks about male-bonding. Inspired by the episode, Martin heads to a bonding workshop, but finds it less than informative. However, upon returning home, Martin meets his "perfect woman."
Martin heads to a travel agent in order to plan his first vacation in a long time and ends up selecting a trip to Bermuda. However, when a family is murdered, Martin must get the widow of the incident signed on as an author so that the editing firm can cash in on the book deal.
Martin develops a crush on a guest on the "Eddie Charles Show" named Sheila. After going out together on a date, Marin and Sheila wind up spending the night together.
While doing his laundry, Martin meets a woman, Nina, and the two develop an instant connection.
As they continue their relationship, Nina suggests that she and Martin take their relationship to the next level: AIDS tests.
While Martin's apartment building undergoes renovations, bricks are set up to fill holes so that birds cannot get in. As Martin and Nina share a romantic dinner together, a protest arises and Nina uses some of the bricks to plug up a factory's drainage pipe and is later arrested for it.
Though friends and family try to help Martin after Nina's arrest, he decides to deal with his problems alone. While sitting in his apartment alone, Martin receives a call from a woman trying to call 555-HELP, a suicide hotline, but accidentally calls Martin's number, which happens to be 555-HELL.
An author, Vernon, arrives at Martin's office to talk about a romance book. Just as Martin admits to Vernon that he hates his job, his new female boss walks in and tries to seduce Martin.
Judith's marriage to Richard Stone is only a short time away, but Richard is no where to be found. Judith turns to Martin for help after a hair cut gone wrong, but their closeness results in the two sleeping together. Will Martin and Judith get back together or will Judith go through with her marriage to Richard Stone?
When a movie is written about the life of Richard Stone, Marin helps the woman portraying Judith in the movie with her scenes and the two end up getting together.
As Martin helps Julie, the woman playing Judith in the movie about Richard Stone, Jeremy lands a role in the movie as himself, which leads to landing a role in the movie being filmed in the next stage over.
An Australian firm buys out Whitestone which means big changes for the company. The new boss, Gibby Fiske, begins to clean house, firing old employees one-by-one. Desperate to keep his job, Martin tells Gibby that he can land the autobiography for the host of "The Eddie Charles Show."
Martin's cousin Phil visits and immediately falls for Toby.
Martin finds an adult magazine and a joint in Jeremy's room. After telling Judith about the incident, Martin and Judith have a talk with Jeremy, but Martin admits that he smoked pot during his younger days as well.
Martin decides to see a therapist when he realizes he has trouble "performing" on dates.
Martin buys a gun after he and Eddie are both mugged twice.
Eddie has Martin read a book written by the sister of a woman he's seeing. Though Martin doesn't like the book, he likes Chloe, the sister. Wanting to score points with Chloe, Martin passes the book along to Gibby who ends up loving it.
A former professor of Martin's offers Martin his own public television access show, "Book Beat." After the first episode airs, Martin is stalked by a fan, Nora.
A girlfriend who walked out on him fifteen years earlier, Veronica makes a surprise visit. Everyone warns Martin to say away from her, but he can help but meeting with his former girlfriend.
Martin and Judith are audited by the IRS. While going through old receipts, Judith learns that Martin had an affair with Nicki Rosen, a friend of Judith's.
Martin has been seeing Charlotte for three weeks and Martin is then informed by Eddie that she was once a porn star.
Gibby tells everyone that they are fired in order to soften them up to the real bad news: there will be no bonuses this year. Meanwhile, Martin plays nickel and dime poker with his co-workers and boss, where the betting quickly rises above nickels and dimes.
An old friend, Bonnie, returns to New York and Martin agrees to watch her stand-up comedy performance, which is anything but comedic.
It's Toby's birthday, and though she has many birthday activities planned, none go as planned and she ends up going with Martin to a wake for his Aunt Minnie.