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The gang reenters Philadelphia's flip-cup tournament (the Flipadelphia) after being banned for 10 years. Trouble is, their old flip-cup rivals have grown up and moved on.
When Dee gets a part in an M. Night Shyamalan film, Mac and Charlie seize a chance to pitch their movie script. But first they have to write it.
Dennis tells the gang how he seduces women, but none of them can get the hang of it.
Mac and Dennis decide to take a break from each other, a development that strains relationships. Meanwhile, "kitten mitten" Charlie helps Dee find her lost cat.
With a merchandising convention in town, the gang tries to build the Paddy's brand by developing marketable products---such as mittens for kittens.
The gang stages a wrestling show for returning troops. Meanwhile, Dee meets a soldier she's been talking to online; but he isn't what she expected.
The gang go to court to talk their way out of a parking ticket they got on the night of the final game of the 2008 World Series.
The Waitress is getting married, and Dee's jealous because she isn't. Meanwhile, the guys try to get the lovelorn Charlie back into the dating scene.
Frank's behavior is more bizarre than usual---so bizarre that even the gang notice---so they decide to stage an intervention.
With a shantytown taking shape outside, Mac and Dennis try to keep Paddy's going in tough times. Meanwhile, Frank and Dee start a family business.
The gang take a road trip. Destination: the Grand Canyon.
Frank, Mac and Dennis try their hand at real estate; Dee arranges to be a surrogate mother for a rich couple; Charlie squares off with a lawyer over the intricacies of the judicial system.
In Season 16, it's a challenge for Ronald "Mac" MacDonald, Charlie Kelly, Dennis Reynolds, Dee Reynolds, and Frank Reynolds who yearn for the past as they attempt to survive in 2023. This year alone, Mac battles with allergies and long-distance dating, Charlie takes on his long-forgotten sisters, Dee fights for rent control and women's athletics, Frank wrestles for his gun, and Dennis struggles to improve his mental health. At the end of the day, they're navigating 2023 with 16 years of baggage as a few figures from their past rear their heads.
