Warren thinks Jack's raucous social life is interfering with business, so he institutes a new policy prohibiting agency employees from dating clients. But when Warren's new girlfriend unceremoniously dumps him, he is suddenly inclined to break his own rules.
Ian's macho twin brother Kevin arrives to make trouble in South Beach while Jack falls prey to Mona, the demanding owner of a photo studio, who has both a penchant for John Travolta and some unusual plans for Jack.
A TV station executive suggests Warren create a dating-game show.
After Jack is ridiculed by the staff for his lascivious behavior, he gets even by persuading his co-workers to stay away from their own vices for a whole week.
Warren and Jack post their client's picture on their website, only to discover that the man is a member of the government's witness protection program.
A sexy client sparks rivalry between Valentina and Carmen, who are both determined to win him over. Meanwhile, Warren's former fiancée shows up at the agency hoping to seduce him.
Jack works to find a match for Valentina's raunchy grandmother Lola in a nearby seniors home after Warren is hospitalized by a spider bite and Jack is left running the agency by himself.
Warren and Jack resolve to attend their high-school reunion determined to prove that they're both successful, desirable men.