A newly-confident Dexter visits the guys with his pregnant wife in tow, only for her to go into labor just as a long streak of bad luck events take place in their lives.
Eager to make her club Kansas City's most popular night spot, Malcolm and Eddie's chief rival, Mia, makes Eddie an incredible offer he may not be able to refuse. Meanwhile, Nicolette enters a short story contest, transporting the gang back in time to the 1920s when two rival nightclub owners resorted to far more villainous tactics to be number one.
With Malcolm sound asleep, robbers break into the apartment and steal all the furniture and strip the house of all its contents. They hire an interior designer to redo the apartment, but find out she not only has an eye for style, but a taste for a con game.
Eddie agrees to buy Malcolm's lottery ticket and has to face the consequences—again and again and again—when the numbers hit.
After Leonard's date publicly humiliates him at the Fifty/Fifty Club, Malcolm and Nicolette try to cheer him up by sharing their ""worst date"" stories. But nothing can top Eddie's date that night when he's lured by a woman named ""Sinful Sally"" to her apartment, unaware that she plans to broadcast their rendezvous live over the Internet.
Malcolm, Eddie, Nicolette, Leonard and Doug head to North Carolina to spend the holiday with Malcolm's Uncle Buddy. But panic sets in when they reach his uncle's empty house and discover the town has been evacuated because of an oncoming hurricane, and now they're caught right in the middle of it.
While vacationing in Las Vegas with Malcolm and his new girlfriend, Eddie can't resist the lure of the crap table. But when his lucky streak turns unlucky to the tune of $50,000, he has no way to pay his debt, until a wealthy female offers to cover his losses on one condition—that she gets to sleep with Malcolm in return.
The duo agrees to listen to a realty sales pitch in order to get a free seven-day cruise.