Sandra is the PR director for the Miss Teen Washington Pageant and she encourages Mary to let Brenda enter. After Mary checks everything out, she allows Brenda to enter. But then next day, the head of the pageant adds a new competition that Mary disapproves of: Bikini Aerobics. She goes down to talk to Justin and he says that he can't get rid of that portion of the show or the cable company won't air it. When she and Brenda go backstage, they find out that the other girls feel as though that portion of the show is embarrassing and degrading. They decide to boycott, with the help of Bert Parks (the host) and Sandra, who feel as though she has been cheated by Justin. Sandra, Mary, Pearl and Rose are ""the teens"" who are in the pageant, and when the time arrives for the bikini competition, the cable guy and Justin tear the contract up, saying that they didn't want to see a senior citizen in a bikini! They go on with ""Plan B"" which is where the teens actually come out on stage for the eveni

Sandra's cousin Conchita (also played by Jackee) comes to visit, and her finacee follows her to America. Conchita does not want to marry Carlos in an arranged marriage so she asks Sandra to tell him for her. The two go back and forth with whether or not they want to marry each other, until finally Conchita realizes that she does love Carlos and they decide to get married.

Brenda is a star track star and her coach comes over to the Jenkins' for a cup of coffee and brings a friend of his-- Willie Amakye from Ghana. Willie needs to raise money to stay in America and train for the Olympics so Mary suggests a neighborhood marathon. He even gets his friend Florence Griffith Joyner to participate. Mary solicits all of the sponsors, but when Brenda loses a track race, she loses her confidence also. She decides not to run and Flo Jo tries to convince her that you can't give up because of one loss. When the snow causes all runners to quit, Willie continues runninig because he says he has to raise the money. When Brenda sees his determination, she decides to run alongside him.

Mary is a star player of ""Family Feud""... in her house. She decides to try out for the show when it visits Washington D.C. Sandra also decides to try out, and when she and Mary argue during the interview, the producers decide to air a Neighbor's version of ""Family Feud."" She and Sandra pick teams from a hat and Sandra's team wins on the show. But in the final round, they only make 199 points-- one point away from 200, which was needed to win. Sandra decides to split the money they won (almost $1000) among everyone on both teams.

Lester and Raymond decide to buy a Jaoanese Restaurant together. Pearl and Rose each put in $500 and receive a stock of the restaurant. When the deal is sealed, the kitchen staff all quit, right before a Japanese tour group arrive to eat. They all hustle to try to serve them but it is a disaster, as Pearl cannot cook (or understand) Japanese food and the ladies are horrible waitresses. The chef returns and decides to buy the restaurant from Lester and Raymond at the same price they bought it for.

When Mary throws pictures of Sandra, Rose and Pearl away, they each find them and reminisce over the past 3 227 seasons.

Alexandria doesn't celebrate Christmas so everyone tries to get her to feel the spirit of the holiday. Sandra meets a Santa on the street and brings him upstairs to meet Alexandria. But when everyone leaves the room, he steals all of their presents. Mary, Lester, Sandra, Rose and Pearl each decide seperately to dress up as Santa and bring gifts to make Alexandria think that Santa had a change of heart. However, since the police is looking for Santa thieves, they all end up in jail as suspects. Brenda, Calvin and Alexandria come to the precinct to get them all out and the real Santa is caught. He still has their presents. And Alexandria realizes how far everyone went to get her into the holiday spirit and she appreciates it.

Sandra gets a job as a meter maid. When Pearl gets her purse snatched while on her way to the bank with Mary and Rose's dues, Sandra and Mary hatch up an idea to stage a stake-out in the park. Rose and Mary pose as elderly women. They become suspicious when a skater continues to skate past them and suspect that he is the mugger. An older man comes and sits on the bench with Mary and Rose. He eventually snatches their purses and the skater, who is an undercover cop tries to handcuff him. Sandra decides to be the hero when she jumps in, but she handcuffs the skater instead and the mugger gets away. When they get home, Pearl realizes that the dues money wasn't in her purse but pinned inside another bra.

When Mary and Lester are on their way to the airport their tickets are stolen by a pick pocket who is running from the cops. As Lester and the police officer go after the man Mary waits in the cab and imagines their lives as the movie Casablanca. In the end, Lester gets the tickets back and they go off to the airport.

When Mary and Lester go to parent's night a Brenda's school, Mary does not like the playfulness of her history teacher, or the fact that he does not give tests or homework. She asks the principal to monitor his class, but the principal fires him. When Brenda finds out that Mary was the ""loud-mouth"" parent that squealed, she is mad at Mary, but also feels sorry for Dylan, who she says is a good teacher. Meanwhile, Sandra is a sales representative for Luscious Lingerie, and when her door-to-door sales are not profitable, she asks Mary if she can host a lingerie party at her apt. Mary agrees, but only if Dylan can assist her, to make some money for himself. The party is successful, but Dylan says his heart is with teaching. When she finds out that Brenda and Calvin remember what Dylan's teaching them, she talks to the principal to get his job back. Dylan winds up moving into 227.

Sandra asks Rose to take her place on a blind date. Little does she know that her blind date is a Prince! The ladies each take turns trying to impress him, but it's Brenda who catches his attention. She agrees to marry him, thinking that maybe her parents won't think that her proposed trip to Europe that summer isn't so bad after all. The Jenkins decide to let her go through with the plan, but instead Calvin will be in a masked costume. They were thinking that Brenda will stop the ceremony before it's complete. But Brenda hears that plan and also decides not to stop the ceremony. The Prince finds out about the plan and his chauffeur grabs Calvin while the Prince takes his place in the ceremony. After the ceremony is complete everyone finds out that Brenda actually married the Prince. The Jenkins are furious, and so is Brenda. She apologizes for saying that she'd marry him just to make her parents mad, and they get a divorce.

Mary goes on a hike with the Buttercups, the group of young girls (like the Girl Scouts) that Alexandria wants to join. Sandra comes along also, thinking that the handsome leader would be there. They all get lost and decide to stay in a cabin until the next day. Brenda and Lester hear on the radio that a woman escaped from a mental institution and is on the loose in the park. The ladies later hear the same message. When the ladies meet Ranger Granger they assume she is the escaped lunatic disguised as a ranger. When she is sleeping, they tie her up. That's when the real lunatic showed up. The ladies wind up tying Lucinda Merkle up, and the police take her back to the asylum.

When Sandra goes on the Love Connection, she chooses Gary because he is the owner of a jewelry store. When he arrives, Mary is in Sandra's apt to greet him, because Sandra has gotten Mary's phone glued to her fingernail. They decide not to eat out, and Gary says that he will cook for Sandra. The problem is, Sandra doesn't have any food in her apt, so she goes to the Jenkins' to ""borrow"" food. While in the kitchen, Lester arrives with the loan officer. It turns out that the loan officer is Gary's ex-wife! Mary tries to keep Sandra and Gary in the kitchen until Cynthia leaves. When she finally leaves, the coast is clear...until Cynthia comes back and sees Gary in the apt. She tells Lester that the deal is off and throws a pie in Gary's face. She later returns to apologize for being unprofessional, but once again runs into Gary, this time kissing Sandra. She calls the deal off once again, and the entire group gets into an argument outside 227. Sandra later finds out that Gary is the owner

Mary's cookie sales at Brenda's school is putting Ed's Cookies out of business. He proposes that she go into business with him. They agree, but when Mary realizes that she isn't making more than she was when she was alone, she pulls out of the deal. Ed comes by the next day and offers Mary $15,000 for the recipe. She eventually sells it, but not before Lester comes in and shows her a headline that reads, Big Company to buy cookie recipe from local baker for $100,000. Mary devises a plan to get the recipe back. Before Ed can sell the recipe, she comes in with Sandra dressed as a nun and tells the buyer that the recipe actually belongs to ""Sister Sandra."" He doesn't want to cheat the convent out of their money so he decides not to buy from Sandra. Mary later finds out that her grandmother's cookie recipe is actually Famous Amos' recipe.

Sandra's new boyfriend keeps showering her with gifts. When everyone meets him, they are surprised-- he is Pearl's age! He asks Sandra to marry him and gives her a day to think about it. She tells him no, and he has a heart attack. In the hospital, Mary and Sandra pose as doctor and nurse because the rude desk nurse will not let them see him. Sandra decides to tell him that she will marry him, since she thinks that he is on his death bed and it would make him happy. The next day when they return to the hospital, Abner has made a recovery. It turns out that his ""heart attack"" was gas, and he says he is ready to get married to the nurse that raised his spirits. He thinks that nurse was the rude desk RN, nurse Grubb, and Sandra doesn't object. Meanwhile, Brenda, Calvin and Alexandria are trying to raise ticket money for a Prince concert.

Mary tells the kids that she has the hookup to get Run DMC to play at their prom, but the problem is the kids cannot afford the $5000 fee. Dylan takes their money and invests it in a stock, which goes belly-up. They end up losing all of their money and cannot afford to have the prom in a hotel anymore. Instead, it is held outside 227, much to the kids' displeasure. Both Mary and Dylan go where Run DMC is and dress up as rappers to convince them to come. Dylan succeeds and Run DMC show up to rap at the prom.

Both Mary and Sandra get commissioned to the same murder trial. There are 11 votes guilty and 1 vote not-guilty, Sandra choosing not-guilty. After hours, she still has not changed her vote and Mary is annoyed because her anniversary is that night. They vote one last time, and this time the 1 not-guilty vote is from Mary. The judge sequesters them for the evening in a hotel and Mary is going to miss her anniversary dinner with Lester. Lester sneaks into the hotel room and brings Mary caviar and champagne. The next day, Mary presents her theory of what actually happened (pertaining to the ""murder"" on the boat) and the jury agrees and they all vote not-guilty. Their verdict was the right one, because later the ""murdered victim"" was found on the French Riviera with her husband's best friend, which was stated in a voice-over.

Sandra bets Mary and Rose that she can stay away from men better than they can stick to their diet. They each send temptations the other's way but it all comes to a head when Lester's business partner comes over for dinner. He tells the Jenkins that he can get Sandra to kiss him so the bet will be over, but if he can't, then he will give Mary and Lester 2 weeks free hotel stay at a hotel that he owns in Jamaica. Well, now Mary is rooting for Sandra to stay away from men. Rose comes downstairs, but she wants Sandra to kiss Howard because she is tired of dieting. Finally, Howard tricks Sandra and kisses her, but both she and Rose are relieved because now they can both do what they want!

Lester hires a young ex-con from the persuasion on Mary. They both admit that he is doing a great job and are happy with him until he asks Brenda out. They object and eventually tell Mike that he is not allowed to see Brenda. He feels dejected and decides he may as well not take the GED test as planned, because people will always see him as an ex-con. The real Joe Clark of the ""Lean on Me"" fame comes and gives him words of encouragement and he decides to take the test. The Jenkins apologize for the way they treated him.

When Pearl, Mary, Rose and Sandra get locked into the laundry room, they all reminisce about how they each arrived at 227. Pearl moved in with her mother, Rose lived across the hall from a loud rock band, and Lester had just lost his job at a construction site, while Mary was pregnant with Brenda. Lester eventually finds them all in the laundry room and opens the door so they can leave. By that time Brenda and Calvin had joined the 4 ladies.

Sandra has moved to New York, but finds herself jobless after she finds out that the film company that she works for specializes in porn films! So once she find her apt., she meet a woman who tells her about a job opening at her job. Sandra goes with her the next day and gets the job at the spa. Sandra finds out that her new friend's boyfriend is using her, but when she tells her, she doesn't believe Sandra. Finally, when she hears it for herself, she cuts the boyfriends loose and her and Sandra are back on good terms.

Rose sells the building and a sister of Lester's friends comes to visit. She staying with the Jenkins and is driving them crazy. She gets hired as the building manager. The company that bought 227 wants to demolish it and the tenants become mad at Rose for selling the building. Eva found originally sheet music from John Philip Sousa and the building is declared a historical landmark, so it can't get torn down.