Mary invites Sandra and her date, an eligible Congressman, to a dinner for Brenda's teacher who is attracted to the legislator.

Everyone goes to Atlantic City for a Luther Vandross concert for Pearl's birthday. While there, Mary goes on a lucky streak at gambling. Lester decided to go into business with Julian in owning part of a promising boxer. Pearl looks for Luther Vandross, but when a mob goes after Luther, her antique diamond brooch is stolen. Brenda & Calvin try sneaking into the casino in hopes of winning a new car. Travis finds out that his tickets for the Luther Vandross concert weren't ordered and decided to enter a comedy contest to win tickets for Pearl. Meanwhile Warren has planned a special weekend for Rose, and he asks her to marry him. When she goes to tell her friends, Warren make a pass at another woman and is spotted by Mary. But before Mary can tell Rose, Rose asks her to be her matron of honor.

Just before Brenda gets ready to graduate high school, Mary is rushed to the hospital with appendicitis. Mary gets a lesson in plastic surgery from her roomie; and Lester gives low marks to his father's girlfriend.

When the daughter of Lester's friend comes to stay with the Jenkins until the dorms at Howard University open, she gets a taste of the big city first hand. Sandra is behind on rent for three months and she decides to get a roommate. Sweet, shy, quiet Donna becomes her roommate after the dorm overbooked. She takes a lesson from Sandra and begins dressing, walking, talking, and acting like her. She steals Sandra's boyfriend and when Mary talks to her about the new Donna, she gets upset and leaves. Then her parents show up to check on their ""baby."" Mary stalls until finally Donna comes back. They talk privately and Donna apologizes and admits that she was not ready for ""life in the fast lane.""

Mary and Lester go to a toy store to purchase toys for kids in the hospital. When they get there, the guy lets them in even though the sign on the door says closed. The Jenkins discover that he is attempting to rob the place. Pee Wee Herman comes into the store to purchase some things, so he is taken ""hostage"" along with Mary and Lester. Later on, Sandra comes and she is also escorted to the back of the store. The entire gang is tied up. They think of ways to escape. Their plan for Sandra to entice the robber changes courses a little when Pee Wee actually saves the day by throwing bubbles into his eyes.

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

Lester's construction company has the chance to be purchased by a multi-national company. The lawyer that is over the proposed merger sub leases the apt and next door, and he and Mary start off on the wrong foot from the beginning. He requests tickets to see the Pointer Sisters, makes Mary cook a steak, (after she'd already made fish) mistakes her for the maid and tells her to clean his apt for $3.00 and hour. When Mary can't get tickets, she, Rose and Sandra dress up as the Pointer Sisters and host a party for Thurmond. Lester decides that he does not want to sell.

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.

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.

Mary's luck runs out in Atlantic City and she loses all of her winnings, including $3000 she promised Lester. Meanwhile, Warren and the mystery woman meet again and Rose spots them in a compromising position. She breaks off the engagement, but since neither will accept the ring, Mary takes it for safe-keeping. Travis gets stage fright at the comedy show and Dylan takes his place. He wins, but is disqualified because he never officially entered making Pearl lose out on seeing Luther. After confessing to Lester she lost all her money, Mary notices Rose's ring has been stolen. Mary stops the woman and it turns out she is the woman Warren had been seeing. Warren admits he was seeing her because he knew she was the jewel thief who stole Pearl's brooch, and even Luther Vandross' watch, so she would let her guard down. Rose & Warren get married in Atlantic City afterall. At the wedding, Luther comes to thank Mary for getting him his watch back, and in return he agrees to sing at the wed

The Social Security office says that Pearl is dead, and the resulting protest lands Pearl, Mary and Rose in jail.

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.

Sandra is writing a romance novel whose characters resemble the residents of 227: Marie, Rosita, and Pearlie Mae. With Mary up against Emma Johnson for the presidency of the Ladies' Auxiliary, she becomes nervous when Emma receives a copy of Sandra's book. She and the Rev. come to the Jenkins' home when Sandra drops by and gives Emma the newest chapter of her book, introducing a new character: Emily (who resembles Emma). Emma changes her mind about blabbing to the Rev. and resigns from the running for president. Mary becomes president.

Calvin befriends a new kid named Ron who says that his money comes from his rich uncle. He buys Calvin a new pair of shoes and offers to take Calvin and Brenda to a Stevie Wonder Concert. Mary doesn't like the way Ron is ""trying to buy friends."" For $50, Ron gets Calvin to give someone a sealed package and in return he receives $1000 to give back to Ron. Once Pearl and Mary find out, they conclude that Ron is a drug dealer. Mary goes to talk to Ron's mother about his free spending and the fact that he is a drug dealer, but his mother refuses to believe Mary. Calvin confronts Ron about using him to deliver drugs and Ron admits that he used Calvin and all it cost him was a pair of shoes. Later that day at a drug meeting, Ron's mother shows up and tells the 227 residents that Ron was stabbed to death in a drug deal gone bad.

Sandra overhears how Mitchell interacts with his students and she tells him that he needs to continue teaching because he needs the kids and much as they need him. Sandra and Mitchell confide in the Jenkins separately that they are not ready to get married. When the minister asks if anyone objects, they both raise their hands. They decide that they are not the that the other should marry and need more time to decide whether or not they are ready to get married. Meanwhile, the ladies try to teach Sandra how to cook.

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!

Mary dreams that she's homeless after misinterpreting a plea for help from a street person (homeless advocate Theodore Hayes) as a threat to her safety.

When Lester decides to rent a hotel room for the weekend, Mary plans a cruise, and the ladies plan a surprise party for Mary and Lester's Anniversary, it's all Brenda can take to keep it a secret. She decides to tell them what the other's are planning for the weekend and they all agree to the party. When Lester and Mary's parents arrive they argue about everything. Lester ends up getting sick and the party ends up being cancelled. Lester and Mary decide to take a cruise later on to celebrate the anniversary.

When Sandra meets Brenda's math teacher at the Jenkins' apt., they begin dating and he gets more serious than Sandra. Then, Sandra comes by the Jenkins' with her new rich date, while Mitchell is visiting. To get Sandra back, he spends all his money trying to wine and dine her. One night at the Piano Bar he announces that he is going to begin working as a computer executive, thereby making more money. Mary talks to Sandra and says that Mitchell loves being a teacher and is only giving it up for Sandra and to make more money. He and Sandra talk and the show closes with Sandra announcing their engagement.

When Mary goes to a seminar about success, she meets a business man who wants to build a $50 million museum. She tells him that Lester is a big time contractor and sets up a meeting date. She uses Sandra's boyfriend's penthouse across the street to prove to Mr. Mortimer that she and Lester have lots of money. When Sandra's boyfriend comes home early, Mary's plan begins to fall apart. She admits what was going on to Mr. Mortimer and his wife. They understand, because Mrs. Mortimer says she, too, would do almost anything to aid in her husband's success. They end up using Lester's company for a smaller project.

When Mary's high school friend comes to visit, everyone is excited to meet her because she is a famous writer, psychologist, and romance adviser (like Dr. Ruth). Mary imagines what it would be like to be that famous and well liked. She begins to get jealous when Brenda tells her that she wants to be like Dr. Butler. She tells Lester how she feels and he admits that he thinks Thelma may be jealous of Mary and her stable life. Mary and Thelma get in an argument about who is jealous of whom and they bring up a lot of things that happened in the past. They wind up laughing about how silly they were acting and make up.

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

Mary decides to invite her landlord Julian to her Christmas Eve bash in hopes of livening things up.

Brenda's grandfather arrives with a Wailing Eddie record in tow. While letting Brenda listen to it, she accidentally scratches it and her grandfather is devastated. She doesn't understand what's so special about the blues anyway. Mary and Lester find another rare copy, and it too is ruined accidentally by Brenda. This episode is cut with scenes of Sandra and Rose singing the blues and narrated by Brenda. Towards the end of the episode, she finally understands what the blue is all about, because she has them. Her grandfather is upset with her and everyone is coming down hard on her about the broken record. She and her grandfather reconcile and Pearl gets Wailing Eddie to come to the Jenkins' and sing.

Lester is informed that he has an inheritance coming to him. But before he can collect it, he has to live with some distant relatives and discovers that they are country folk and white.