While Frank, Mac, and Dennis try their hand at real estate, Dee arranges to be a surrogate mother to a wealthy couple with a sweet pool.
Meanwhile, Charlie faces off with a lawyer on the intricacies of the judicial system.
Mac and Dennis deal with the economic strain by making Charlie and Dee prove their worth.
When they fail to do so, Dee quits and Charlie gets fired.
The gang makes many stops along the way (switching cars, the Italian Market to buy wicker furniture for the trailer and fruit for Charlie, bathroom stops, and picking up a hitchhiker).
Frank attempts suicide because of a recent financial loss that he attributes to the recession.
Meanwhile, the soldier (Travis Schuldt) Dee has been chatting with online is not what she expected.
This season also sees Frank becoming more self-destructive and worried over his mortality: becomes a slobbering drunk, attempts to hang himself after losing all his money, has sex with Artemis (the strange actress from Sweet Dee's acting class), and tries to sleep with the same women as Dennis...after Mac has had his shot at them.
The gang then decide to take a trip to the Grand Canyon as part of an item on Frank's bucket list—but the trip ends before it can begin after several unfortunate events.
Dee finds out The Waitress is getting married and she is jealous so she tries (with the help of Frank, Artemis, Mrs. Dennis and Mac, fearful Charlie will lose his mind and take it out on them, try to find Charlie a girlfriend with online dating.
Dee learns that The Waitress went to high school with her ("...