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.
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.