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.

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

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

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 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 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.

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.

Sandra begins dating a basketball player who rubs Mary the wrong way from their first meeting. He comes across as rude and arrogant. Calvin idolizes him and mimics his attitude. Brenda doesn't like hanging around the ""new"" Calvin. When Calvin hears how the Rocketman talks to Sandra in an argument, and hears the Rocketman call him ""some dumb kid,"" he changes his opinion of Rocketman and realizes that he was acting like a jerk.

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.

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.

On the way home from running errands, Mary hits a BMW, breaking the tail light. From the persuasion of Rose, she decides to leave a note on the car. The next day, after no one has arrived to see the car, Mary wants to remove her note. However, another car comes by and nearly totals it, but then drives away. Before Mary can get to the car and remove her note, the owner comes out of an apartment and sees her note. Sandra tells Mary that she needs to use her "femininity" to get out of paying for the total damages. Mary says that she can't do that, so Sandra poses as Mary when the owner comes by to talk to Mary about the damages. Everything goes well until Lester comes home and their lie unfolds. Everything gets straightened out between Mary, Lester, and the car owner (Marvin), ending with a date for Sandra and a new friend for the Jenkins. Meanwhile, Mary tells Brenda that she cannot go skating with Calvin because she lied.

Lester's old boss comes to visit the Jenkins from Hawaii. While there, Rose hires him as the building repairman and lets him live an efficiency on the third floor. Pearl begins to notice that people go up to visit Lou and never return. She and Mary investigate and find out that Lou is homeless and his homeless friends are the ones that have come to live with Lou. It turns out his business in Hawaii went belly-up, and Lou lost everything. Mary has sympathy for them and feeds them, while trying to keep the news from Rose, because she would have to put them out based on the housing codes that they are breaking. Lester finds out about an abandoned building that his company will fix-up so the homeless people will have some place to live. This will also give Lou the chance to get back into business again.

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.

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

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 the landlord dies, everyone believes that Sandra will become the new landlord, including Sandra. She assures Mary that once she becomes the new landlord that Mary will have to find a new place to live after her lease runs out. The tenants all go to the will reading and it is discovered that he actually leaves the building to Rose. However, when Mary thought that Sandra would get ownership of the building, she called a building inspector to check out 227. He states that 227 is in need of numerous repairs, more than the tenants can afford.

While reading the newspaper, Rose and Pearl choose 6 numbers related to an article that is in it. However, Mary thinks the lottery's a waste of time and money. But with a big jackpot, Rose & Pearl don't care. Mary preaches to the girls what a waste of time it is, so the girls agreed. Lester buys Mary a scratch off ticket and she wins $10. However, while waiting in line to redeem it, she gets a lottery play slip and gets numbers from the same newspaper article. Sandra spots her and then she know she's in trouble. Rose & Pearl enter Mary's apartment and were mad that after she preached about the evil of playing the lottery, she buys a ticket for herself. So she offers to split any winnings should it be a winning ticket. The Pick 6 is a winning ticket and that not only Mary won, but many people in the 227 apartment building won, as well as much of Washington DC! The big jackpot turns out to be worth $266 & that Mary, Rose & Pearl will each get $88.67!

When Brenda meets a cute boy she decides to invite him to her party Saturday night. After getting permission to actually have the party, she then hears Sandra tell a story about how when she was young and wanted to get to know a boy better, she would ""mistakenly"" tell him the wrong day of the party. Brenda tries the idea and invites Ken over for Friday night instead, hoping that when he gets there he will meet her parents and stay for dinner. But Mary and Lester decide to go out to eat and are not home when Ken arrives. Brenda decides to let him come in anyway, just to have a drink, but then Calvin shows up to drop off chairs for the party. When she tells them they need to leave, Mary and Lester arrive home and the boys hide. Mary and Lester eventually catch the boys in the house.

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.

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.

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.

When Sandra tells Mary how she can't keep a job because of jealous wives, Mary asks Lester if he knows of any job openings. He admits that his company needs a receptionist for their main office and Sandra gets the job. However, Pearl and Rose worry Mary so much about Sandra working with Lester that Mary becomes suspicious and jealous.

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.