When Frank decides to put the gang on 'Charlie Work' instead of Charlie, they get furious and try to change that. Since Charlie is now manager, the gang does various favors to get out of it. And at the same time Mac banged Dennis' mom and Dennis wants to get back at him by trying to bang Macs mom.
Tensions run high in the gang when Mac courts Dennis and Dee's mom and the two organize a stakeout to blackmail Frank and get out of "Charlie work".
- After being demoted by their father to do "Charlie Jobs", Dennis and Dee come up with ways to get their original jobs back; Frank promoted Charlie to manager at the end of "Dennis and Dee Go on Welfare." Dennis decides to go on a date with the waitress whom Charlie likes. Dee has to come up with her own idea. Turning the events on to Mac, he is sent by Frank to get his toupee because he has a date that night with an old flame who he remembers as a wild animal. Frank hopes to rekindle the spark and needs his toupee, which is at his house. Mac goes to his house to pick it up and is met by Mrs. Reynolds. After he gets the toupee and is on his way out, Mrs. Reynolds is in his path with nothing but a green negligee and she takes it off. Mac is left stunned.
That night, Dennis and the waitress go on their date, but not before Dennis reveals to Charlie who his date is. Dennis makes a proposition to Charlie that if he calls by 10:30 he won't bang the waitress. Charlie is angry and starts plotting revenge. Dennis and the waitress are leaving when Mac enters the pub. It's awkward for Mac seeing Dennis since he has just seen his mom naked. Dennis then goes on his date and Mac talks to Charlie. Mac confesses what happened between him and the older woman and even though she's Dennis and Dee's mom, he wants to have sex with her. Charlie agrees and encourages Mac.
It's almost 10:30 and Charlie still hasn't called. The waitress asks why Dennis keeps looking at his phone and he says he's expecting an important call. To stall for time, Dennis says "I love you" to the waitress and then she wants to sleep with him. As she leans in to kiss him, his phone rings, Charlie tells him to meet at a place, and Dennis leaves the waitress hanging. Dennis meets Charlie and Charlie says, "I know something you don't know."
The next day, Dennis and Charlie, parked outside of the Reynolds house, see Mac getting kissed goodbye by Barbara Reynolds. Dennis wants to kill Mac, but Charlie says it will not undo the damage that's already been done. So to get back at Mac, Dennis has to sleep with his mom. Dennis tries to do that, but Mac's mom finds him unattractive. Even with flowers and sweets he is turned down. She herself is also unattractive, as she is a smoker, couch potato, and a little on the heavy side. Dennis is appalled that an ugly woman like her would not want to sleep with a guy like him. While he is trying to do this, Dee and the waitress are across the street watching him. The waitress is in disbelief and Dee tells her not to trust Dennis. Dee gets a phone call, kicks the waitress out of the car, so as not to be rude while she's on the phone, and takes the call. Its Charlie who has a second phase in his plan. She reluctantly follows him, with her main objective as becoming bartender again still in her mind.
Dennis is at his apartment, still upset by the rejection when Dee comes bursting in and telling him that in order to get her job back, she has to sleep with Charlie (as this is Charlie's second phase). Dennis wants to kill Charlie, but Dee says he needs to do something worse than murder. He needs to sleep with Charlie's mom. Dee ends up not sleeping with Charlie. So Dennis tries to do that, again with flowers and sweets, but Charlie's mom finds him sexually unattractive. Dennis finds this incredulous, to be turned down by two older women. Again, Dee and the waitress are outside, spying on Dennis. The waitress just cannot believe what she is witnessing. Dee calls her brother a pervert. T hen there is a third phase. Meanwhile, Frank brings Mac along as a wingman to find some younger women, as his date with his old flame went sour very fast. He wants to act like he's in his twenties where his date had grown up a long time ago. She married and even had seven kids, two from her husband's previous marriage. Mac finds out from Frank that Barbara likes money and dancing.
The final phase of Charlie's plan at payback is to go on a date with the waitress. Dee set up a date for the two, which the waitress really does not want to go on, but does, and Charlie gets help from Dee to get a wardrobe for the date. Mac is told by Barbara that she slept with him solely for the purpose of making Frank jealous, which did not work because he does not know about the fleeting affair. Mac gets dumped, even after he offers Barbara a wad of cash. Dennis confronts him as Mac leaves the house. The two begin to fight on the lawn.
Later that night, Charlie is ready to go on the date with the waitress. Mac and Dennis are at the bar getting drunk and recovering from their recent fight. Dee and Charlie come out of his office; Dee got her job back for doing this last phase. Frank and the waitress come in, just in time for the date. Then the waitress yells at Dennis for being a pervert and trying to sleep with older women, but he didn't want to sleep with her. So she ended up sleeping with Frank. The episode ends with a camera shot of a heartbroken and tearing Charlie.