Everyone worries when Frank announces that he's going to propose to his hooker girlfriend Roxy. Charlie tries to get a better kind of woman for him, as Dee hopes to change Roxy into a "Pretty Woman". Dennis, meanwhile, becomes concerned over Mac's weight gain.
Hoping to recapture some childhood memories, Dee and Dennis bring the gang to the Jersey Shore. Once there, the two try desperately to relive some happy moments while Frank and Mac get stranded in the ocean and Charlie happens upon the Waitress.
Frank inadvertently invests in a children's beauty pageant with a man who turned out to be a diddler. Unable to back out, he moves the show on while trying not to make himself look suspicious. The guys, meanwhile, back the lone boy, as former children's pageant winner Dee joins in via the front-runner's sister.
Not wanting Frank to make all the decisions for the bar anymore, the guys set up a democratic system. However, it proves troublesome for Mac and Charlie who run to Dee in exchange for helping her as the IRS prepares to audit her after she claims her surrogate child as a dependent.
When Frank's long lost brother Gino shows up at the bar, the two of them tell the gang about the jazz club they ran in the 1960s and 70s, and how they fell out over Shadynasty, a singer who was the love of both of their lives.
As a hurricane threatens Philadelphia, Mac, Dennis and Charlie go to a mall to buy supplies and check out the large breasted TV reporter broadcasting from there, while Frank and Dee prepare Paddy's, and its basement bunker, for the storm.
Another rainy day in Philadelphia. The gang can't go out and play, so they stay indoors and play a board game of their own devising. (It doesn't much resemble Chutes and Ladders). They also drink.
While Dennis and Charlie track down an annoying Paddy's patron the old-fashioned way, Dee and Mac cyberstalk him. Frank is online as well, trying to boost business at the bar. Things go viral, and not in a good way for Frank.
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.
Step inside the confession booth with Mac as he tells a befuddled priest why his fatness is the fault of the other members of The Gang.
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 - make that trip - down memory lane.
The gang come up with a new plan to buff their tarnished high-school reputations at their high-school reunion.