The fifth season of the American television comedy series Rules of Engagement premiered on September 20, 2010. It consisted of 24 episodes, each running approximately 22 minutes in length, marking the first time that the program received a full-season order. CBS initially broadcast the fifth season on Mondays at 8:30 pm ET in the United States between How I Met Your Mother and Two and a Half Men. In February, the show moved to 8:30 ET on Thursdays, following The Big Bang Theory.
Jeff tells Adam his secret for keeping track of Audrey's mistakes and how he uses that list to keep Audrey from getting too upset with him when he makes mistakes. Russell hoping to get a girl sends a nasty e-mail to Timmy's love interest.
Jeff wants to see if he can get Audrey to get the rug back after Jeff gets sentimental about the rug and reminds Audrey about all the good times they had on that rug.
Audrey tries to be more spontaneous in the bedroom with Jeff. Meanwhile, Russell invites Timmy to join him on a business trip to distract him from his fear of flying.
When Jeff can't get out of the lease for a retail space he rented for Audrey's fleeting cookie business, he and Adam invent a new game involving the heads of mannequins. Meanwhile, Russell and Timmy go on a double date.
When Russell's trust fund is cut off by his mother, he gets a taste of how life will be after moving in with Timmy. Meanwhile, Audrey helps Jeff impress his boss in order to get a raise.
Jeff struggles to figure out how to ask his co-workers to donate money for Audrey's 10K charity run after telling them that he doesn't want to participate in their fundraisers anymore.
When Russell decides to borrow a Holiday concept of gift-giving from Adam, both Adam and his co-workers are in for surprises. Meanwhile, Audrey wants to make people laugh at Jeff's Holiday party.
When Jeff discovers that a guy is giving Audrey home pilates classes, he wants to make a change. Meanwhile, Adam tells Jennifer specifics about his football past.
When an old photo of Jeff appears in an art gallery, he decides it's time to make some changes in his life. Meanwhile, Russell experiences a slump with women until he sees a familiar face.
Jeff and Audrey get a surprise that their family may soon double in size. Russell in his latest scheme to date a girl decides to throw a party Ford Timmy who recently became a citizen, now the question is will the party have the desired effect for Russell?
Russell gets Timmy and to see if he can figure out why to Liz is attracted to the other man and not Russell. Jeff doesn't like the idea that Audrey is making almost the same amount of money as he does.
Russell books a cruise that he thinks is filled with "red hot" ladies but instead it's filled with ladies from the Red Hat society. Meanwhile, Timmy tries to help Jeff and Audrey settle an argument.