While Frank, Mac, and Dennis try their hand at real estate, Dee arranges to be a surrogate mother to a wealthy couple with a pool; Charlie faces off with a lawyer on the intricacies of the judicial system.
The Gang tries to expand their horizons by going on a road trip to the Grand Canyon. Despite the guys' attempts to leave Dee behind, the entire group travels in Dee's small car and the back of a U-HAUL trailer, making many stops along the way: bathroom stops, the Italian Market to buy furniture for the trailer and fruit for Charlie, and picking up a hitchhiker.
Frank attempts suicide because of a recent financial loss he attributes to the recession. Mac and Dennis deal with the economic strain by making Charlie and Dee prove their worth; when they can't, Dee quits and Charlie gets fired. Dee then teams up with Frank, who feels better after financially cutting off the Gang, to start a business; the business fails and the good feeling flees. Mac and Dennis try to emulate the Dave & Buster's business model with newly-impoverished Americans who are residin
Dennis, Charlie, and Dee stage an intervention on Frank because they no longer enjoy drinking with him; trying to become as depraved as possible, Frank tries to seduce his former sister-in-law (Nora Dunn), whom Mac also pursues while Dennis and Dee deal with their bizarre cousin "Gail the Snail" (Mary Lynn Rajskub).
Jealous that The Waitress is marrying her former boyfriend Brad Fisher (Nick Wechsler), whom she cruelly dumped because of his acne—Dee tries to derail the wedding, enlisting help from Frank, Artemis, Mrs. Kelly, and Mrs. Mac. Fearful that Charlie will lose his mind and take it out on them, Dennis and Mac try to find him a girlfriend with online dating. Dee learns that The Waitress went to high school with her ("... you really are forgettable.")
The Gang describes the tribulations they endured during Game 5 of the World Series, hoping that the judge will clear them of all the citations they received.
There's nothing more American than wrestling, so the Gang decides to put on a wrestling show for the returning troops; Frank wants to go along as the Trashman, but the others disapprove. Meanwhile, the soldier (Travis Schuldt) Dee has been chatting with online is not what she expected. Roddy Piper guest stars.
When a merchandising convention comes to town, the Gang tries to develop marketable products, such as Kitten Mittens, Nudey Pens, Dick Towels, and "Shot"guns in an attempt to build the Paddy's brand, and try to blackmail The Lawyer into helping them.
Mac and Dennis decide to spend some time apart after Dee compares them to an old married couple; Charlie lends his feline expertise to help Dee get her cat out of a wall.
Dennis reveals his foolproof seduction system to the Gang; Charlie tries to use it on The Waitress but doesn't quite grasp the concept; the Gang tells Dee that her boyfriend from "The Gang Wrestles for the Troops" is using the system on her; Mac and Frank reveal their parts in the system.
When Dee gets a part in the new M. Night Shyamalan film, Mac and Charlie seize the chance to pitch their movie script, Frank takes on the role of a talent agent, and although Dennis participates, he spends the whole time typing on his phone.
After a 10-year ban from a local drinking competition, "Flipadelphia," the gang tries to reignite their old rivalry with another local bar. Needing serious practice, the guys head to Dennis' old fraternity house at the University of Pennsylvania to get their game up to speed, only to find new rivals. Meanwhile, Dee hones her skills on her own.