Frank decides to marry his favorite crack-smoking hooker Roxy (Alanna Ubach), so Dee tries to pull a "Pretty Woman" and clean her up. Dennis worries about Mac's health because he has inexplicably gained 50 pounds ("cultivating mass" in his words); the two head to the doctor's office where they both get surprising diagnoses. Charlie pretends to be a millionaire in a scheme to get Frank a date with a woman who is not a prostitute.
Dennis and Dee want to relive their carefree childhood vacation memories, so the Gang takes a trip to the Jersey Shore. Their various meanderings find Charlie connecting with the Waitress, Dennis and Dee discovering a less-innocent side of the Jersey Shore, and Frank and Mac getting lost at sea, then partying with the local "guidos" who rescue them.
Frank inadvertently becomes involved in the child beauty pageant business and is subsequently terrified of being perceived as a pedophile; as Dee plots revenge on the pageant's bratty frontrunner, Mac, Dennis, and Charlie think they've found their dark horse to win 'Frank's Little Beauties.'
Dee is forced to commit some deeply questionable acts to escape an unexpected IRS audit; meanwhile, Mac, Dennis, and Charlie demand a great democracy in bar operations to stop Frank from doing what he pleases with Paddy's profits.
The Gang is shocked to meet Frank's long-lost brother (Jon Polito) when he unexpectedly arrives at Paddy's and reveals Frank's background as proprietor of a nightclub known as "Shadynasty's".
The Gang joins the masses in a race to secure scarce resources as a major storm approaches Philadelphia; Frank refuses to buy into the media hype about the storm; Dennis becomes infatuated with reporter Jackie Denardo (Jessica Collins).
Dee and Dennis face off against Mac, Charlie and Frank in the super-twisted board game they developed years ago. The game has three levels: mind, body, and spirit. Mind is composed of trivia, puzzles, and artistry; body is composed of physical challenge, pain, and endurance; and spirit is composed of emotional battery and public humiliation.
Mac and Dee use the Internet to cyber-stalk a man who shushed them at a trendy bar. Dennis and Charlie stalk him the old fashioned way. Frank tries to drum up business for Paddy's with a viral video.
The Gang's plan to "extract" an "artifact" from a residence is jeopardized when the owners turn out to be home. Having not been noticed on the way in, they must make a plan to get the same result for the way out.
Mac tells a priest why his recent weight gain is The Gang's fault and not his; the Gang's bar achieves a success level it has never seen, and only lowly Charlie takes it seriously. This episode includes scenes produced for the sixth season.
Traffic problems as a result of the President's visit to Philadelphia makes it difficult for the gang to see the summer's biggest film, "Thunder Gun Express".
The gang have much to prove when they attend their high-school reunion. They meet old friends and make new foes as they stroll down memory lane.
The gang come up with a new plan to buff their tarnished high-school reputations at their reunion.