Recovering alcoholic John Hemingway takes the job of night manager in a seedy bus station, where a robbery and a missing bus test his resolve to stay sober.

John goes 30 days without alcohol, and wants to get back together with his wife. Before he can reach her, she serves him with divorce papers.

John is not about to celebrate when his sponsor orders him to be celibate -- especially when it's for six long months.

John's mother, an inveterate con artist, begs him to bail her out of jail, and then becomes the obvious suspect when a batch of credit card slips goes missing from the bus station.

It happened one night, nearly a decade ago. Or so says John, who recalls a visit he made to the bus station in 1987, when he first encountered Catherine and had a profound impact on his current friends.

A young woman informs John that he's one of three men who could be her biological father.

Good fortune follows the appearance of a faint image of Christ on the bus station's wall.

John takes a company physical and is assured not to worry about his high cholesterol level, then the doctor drops dead, prompting John to seek lifestyle advice from Catherine. Meanwhile, Gene and Mahalia both find new loves: Gene's is Sara, a lovely ice skater, but Mahalia's turns out to be another con artist she met at a group for ""single Latinos over 30 who've recently remembered childhood abuse through hypnosis.""

John is upset when his son joins a religious cult, and enlists Dexter's help; Egger's embarassing parents visit.

Dexter accompanies John on a visit to his boyhood home in Chicago -- where John learns his departed father never departed. Meanwhile, Hampton gets flowers from his male doctor.

John tells Catherine that she would love him if she could forget about their past together. Later, he logs onto an computer on-line service as ""Fitzgerald"" and types flirtatious messages to a user named ""Ella."" The two seem perfect for each other and arrange a date -- only to discover that ""Ella"" is of course Catherine. Meanwhile, Dexter tries to convince filmmaker Spike Lee to let him cater the meals for Spike and his film crew while they are in St. Louis. When the overzealous Dexter accidentally injures Spike, who ends up in the hospital, the film company hires Dexter to impersonate Spike in the film until he recovers. Also, John represents Mahalia during a deposition with an opposing lawyer in her custody battle for her children but does more damage than good, while Mahalia almost ruins her case by dating the lawyer.

Now that they're both free and clear, Carly and John agree to a date, but advice from Dexter keeps them apart -- at first. Later on, nothing can. No longer a bum, Oscar opens a shoeshine stand in the bus station. Unfortunately, no one is brave enough to sit under the giant shoe sign hanging menacingly overhead. Meanwhile, John's landlord, Mr. Soulaymanulo comes to the station to berate John for causing a high electricity bill with his electric car. Mr. Soulaymanulo and Mahalia are immediately attracted and begin dating. Later, John gets a huge rebate from the government for driving the electric car, and he pays his landlord extra. When John announces that he and Carly are getting married, everyone expects that some sort of disaster will prevent it. At the wedding, Hampton accidentally reveals that he is a homosexual. Then, after John and Carly exchange vows, Catherine arrives and tells Dexter that she is pregnant with John's child...

Catherine gets the wrong idea when she spies John dancing with Carly, Mahalia is cheered by a passenger passing through.

John's daughter appears topless in a skin magazine, Officer Eggers holds an attractive stranger hostage unless he agrees to impregnate her.

John eagerly accepts when Catherine asks him to father her child, but it's a problematic plan. Meanwhile, Dexter is a housemate in a project similar to MTV's The Real World, a reality-based television show called ""Reality House."" He moves into a rent-free loft with six roommates that he has never met, and their actions are all recorded by an ever-present camera crew. However, Dexter violates the group's cardinal rule --always be ""real"" -- by repeatedly advertising his lunch counter.

John moves into a more upscale apartment and is immediately attracted to his new neighbour, a nurse on the night shift.

The guys gather at John's apartment to view what they think is a vintage porn film, but instead find themselves viewing footage of national security importance -- the assassination of JFK. Meanwhile, Eggers decides she wants to be a mother; and we learn something startling about Oscar's mysterious past.

Dexter dates a beautiful woman who shares John's name, and when Dexter kisses her, he can only see John's face.

Carly's 21-year-old brother has eyes for Catherine, but his age -- and John -- aren't the only obstacles to winning her heart: despite his fabulous income from bike racing, he is illiterate.

Catherine has two house guests: a seven-year-old niece, who invests in Dexter's nine-ball skills, and her jazz musician ex-husband, who wants her back.

Catherine breaks up with John because ""things are too good"", Dexter discovers that his new love Annie has a surprising past, Mahalia loses her new dog, and John's suspicions are aroused by the kindly gentleman who returns it.

After he discovers a collection of short stories he wrote as a young man, earnest John Hemingway enters a writing contest that could send him to Paris, and Catherine hints that she'd like to accompany him. Unfortunately, the story is from John's alcoholic period, and he actually may not have written it: acerbic newspaper chief editor Otto Friedling accuses John of plagiarizing Ernest Hemingway. In a black-and-white fantasy sequence, John's autobiographical story comes to life, with the fantasy John Hemingway (Miller) a would-be writer for whose love both Catherine and Carly vie.

Is it destiny that hooks up John with a pretty yoga instructor for a health spa vacation that he planned with Catherine? If so, why is Catherine on their train? Alone at first, Catherine meets her former high school boyfriend, Todd; and John, who has dumped the annoying Penelope, now does everything he can to keep Catherine from reuniting with Todd.

John and Catherine can't seem to get together for a date because of John's problems with others: Dexter needs him to play tutor for a high school equivalency exam, and Mahalia needs him to help sober up Oscar for a visit from a social worker.

A canine is the centerpiece of the bus station's new security system, Catherine and John try living together, and John's former art professor show up to announce he has incurable cancer and intends to commit suicide.