Charles and James Gordon are young, handsome brothers with conflicting differences. Charles is a workaholic doctor, and James is a fun playboy. They have two friends from college, a local TV weatherman named Dusty, and a bitter divorcee named Mitchell in debt to two ex-wives.

Charles comes to a harsh realization about turning 30 even though he maintains he hasn't changed since he was 21. Later, he and James go two-on-two against a pair of noisy, hoop-playing neighbors.

Terri's breakup with her boyfriend leads to overtures from Mitchell, James and Dusty, each of whom believes she's sending signals. Meanwhile, her true feelings are for Charles, with whom she shares an awkward moment which could change their relationship.

Ladies man James gets played like a broken record when he meets Vanessa, a cold-hearted sex goddess whom the other guys discover is cheating on him. Meanwhile, Charles and Dusty take Mitchell to a support group for divorcés, where he drives everyone crazy.

When Mason, an old college buddy turned sports agent, comes into town he hooks Charles up with all the important athletes and sports parties, and Charles soon takes on the philosophy that it's not what you know but who you know. Meanwhile jealous James, Mitchell and Dusty feel neglected.

When Mitchell's entire family pays an unexpected visit, his father makes him an offer that may change his life. Meanwhile, Charles' interview with football sportscaster Ronnie Lott inspires him to return to the game.

When Dusty meets Daisy at a coffeehouse, it is love at first sight. Worried that such a smart, beautiful woman may hurt their good friend Dusty, the guys put her through a test, which she passes with flying colors. Convinced that she is the one, Dusty pops the question. Meanwhile James, Mitchell and Charles dabble in the stock market.

When Mitchell develops a crush on a teacher at his school, he turns to lady-killer James to teach him the right moves. While on their first date, Mitchell's new image backfires, and he winds up wrecking Dusty's new Porsche. Meanwhile, Charles' new cynical boss, Stuart Franklin, gives him an ultimatum: get an exclusive interview with Barry Bonds of the San Francisco Giants or he loses his job.

Mitchell's plot to boost Dusty's ratings lands them on a runaway elephant. Meanwhile, May makes Charles her new boyfriend to scare off her visiting ex-husband, and James finds competition at work with a beautiful colleague.

Charles struggles with editorial ethics when he discovers a football star in a compromising position. Meanwhile, Mitchell's sister May creates havoc for Dusty when she decides to move back to Chicago. Also, May gets a job working as a waitress at The Corner Pub.

When Charles interviews at Windy City Magazine to head up their sports department, he finds the woman who will determine his fate is Rebecca, his jilted ex-girlfriend. Charles' ethics are soon put to the test when Rebecca gives him an ultimatum - sleep with her and he will get the job. Meanwhile, Dusty, who's terrified of heights, fills in as the station's helicopter traffic reporter.

When May defends Mitchell and Dusty after they get roughed up at the local bar, the embarrassed guys enroll in a karate class comprised of 10-year-olds. Meanwhile, Charles' feature article on retired running back Jim Brown, angers the ex-football star and James takes May on a date.

Dusty, Mitchell and James rent an RV and head out to Lansing, Michigan, for their 10-year high school reunion. However, their road trip is interrupted by a motor home with a mind of it's own and a tornado. While reminiscing, the guys' flashback to their high-school days and the events that led to their friendship. Meanwhile, May, scheming to have the apartment to herself, convinces Charles to leave work and meet the gang at the reunion.