Rules of Engagement is a comedy about the different phases of male/female relationships, as seen through the eyes of an engaged couple, Adam and Jennifer; a long-time married pair, Jeff and Audrey; a single guy on the prowl, Russell; and his office assistant, Timmy. As they find out, the often confusing stages of a relationship can seem like being on a roller coaster: people can describe them to you, but to really know what it's like, you have to take a ride for yourself.
When Audrey thinks her maid needs help getting money to fix her limp, she asks her neighbours to help contribute, only to find out she misunderstood what the maid needed the money for.
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.
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.
When Timmy gets tired of Russell's demands and Audrey gets fed up with her terrible assistant, the two work together to find a solution. Meanwhile, Jeff's superstition gets the best of him as he tries to recreate the exact conditions of the Giants' win.
Jeff listens to Russell about a co-worker and finds himself in trouble. Timmy is sent to get Russell's phone from the apartment of his most recent conquest.
Adam and Jennifer plan a secret wedding; however, a series of unfortunate events puts their plan in jeopardy. Meanwhile, to keep Russell and Timmy from finding out about the ceremony, Adam tells them he is staging an intervention for Jeff, on the fourth season finale of RULES OF ENGAGEMENT.
After Jeff stuns Audrey by remembering their wedding date the surprise is on Jeff. Timmy helps Russell on a date.
Jeff doesn't get any dinner after someone else eats it before he does. Now he has to keep quiet about it.
After being harassed for falling asleep during a movie, Jeff tries to prove to Audrey that he's still young by inviting her to his softball game.
Audrey is surprised by Jeff's sudden interest in her favourite reality show until she discovers the reason. Meanwhile, to Russell's delight, Timmy has second thoughts about his impending arranged marriage.
Audrey tries to persuade Jeff to eat healthier when he is diagnosed with high cholesterol, but he can't help sneaking around with Brenda for unhealthy food. Meanwhile, Russell tries to keep up with his new college intern on the party circuit.
Russell issues a competition between the guys to see who can convince their partners to engage in sex more easily.
Jennifer and Adam decide to go on a trip with Jeff and Audrey but may have wished they had stayed home when they find out the reason they took the trip.
When the gang decides to take a trip to Vermont to check out the fall foliage, they find themselves wishing they had never left home. Meanwhile, Russell has renewed faith in his marriage to Liz.
Jeff and Audrey are in for a big change when Brenda finds out she is pregnant. Timmy is Adam and Jennifer's wedding planner.
Frustrated over the attention a pregnant co-worker is getting, Audrey pretends she too is pregnant in order to get special treatment.
Audrey convinces Jeff to go out on the town and do something exciting after making a profit from the sale of his car. After the lavish night has finished, she regrets the decision after finding out they spent much more than he made.
A battle of wills ensues when Audrey won't admit she hates an armchair that Jeff pretends to love; Russell sues Timmy for sexual harassment.
Audrey is upset when Jeff reveals to her that he doesn't believe she saw her dead grandmother's ghost. Meanwhile, Russell tries to persuade Timmy not to go through with his arranged marriage.
In order to convince Audrey he is making an effort in their relationship, Jeff sends her on a romantic scavenger hunt, with mixed results. Meanwhile, Adam leads Russell to believe that Jen has a sex tape.
Liz wants to have a baby, so she turns to Russell for help. Meanwhile, Timmy takes Jeff's advice on how to attract a co worker, but it all backfires.
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.
Worried about getting his father's approval, Russell gets Liz all dolled up to meet him. Meanwhile, Jeff is more concerned about his guys' weekend being cancelled than Audrey's feelings, and Adam has a new friend (Curtis Armstrong) to drive crazy.
Timmy teaches Russell how to budget after all utilities are suddenly turned off. Audrey tells someone all about publishing and shows off her office.
Jeff has found a way to talk to his wife without having to physically talking to his wife through an app on his phone by telling her what ever he wants by having his voicemail go straight to her voicemail. Adam has a salesman come to his defence after his friends pick on him for some bad choice in picking his clothes.
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