James is upset when Charles places more trust in their pal Dusty than in him. When Charles lists Dusty as his emergency contact instead of his own brother, a hurt James attempts to prove to everyone that he is a responsible ""go-to-guy"". Meanwhile Charles awaits an important date, only to have James' irresponsiblity interfere; and Dusty gets a new roommate when Mitchell leaves wife No. 2.

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 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 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.