Barry, Ben, Bobby, and Jason are best friends with the nickname, ""Four Kings of New York."" When Ben's mother passes away, she passes her swanky apartment onto Ben, who immediatley invites his best friends to move in with him.

The friends use Ben's article assignment about one night stands as an excuse to party all night at an exclusive place. Meanwhile, Barry baby-sits his ex-girlfriend's two kids - twins, and Bobby and Jason try to give each other tips on picking up women, leaving Ben at the bar to learn from his own train-wreck caliber mistakes.

Ben decides to set Barry up on a blind date with a co-worker of his. However, Barry becomes suspicious because Ben didn't ask the girl out himself and is convinced something must be wrong with her. Bobby and Jason, meanwhile, get enrolled in a game of chest. The game climaxes when Jason meets with his boss over a possible promotion.

Barry gets a date with a girl Ben had a crush on in high school. To show his affection, Ben videotaped a poem he wrote back in high school but didn't actually show the tape to her until now. Barry immediately gets jealous once he finds how well his date and Ben get along and decides to make a tape of his own. Meanwhile, because of his insecurity, Jason's boss demotes Jason after he discovers an ""endowment"" Jason possesses. Bobby comes to Jason's aid and tries to reason with his boss.

Ben is chosen to work on a campaign for a Democratic candidate and attends a campaign function with Bobby. Meanwhile, Barry finds Jason eating dinner with a man and is convinced that he is gay. After getting confronted with this, Jason denies being gay but admits that he is something else - a Republican. Ben then questions the friends' relationship after finding their beliefs differ.