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

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 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.

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.

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.

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.

When Mary tries to convince the landlord to order her a new refrigerator, he refuses. Mary then agrees to loan Sandra her apartment for a extravagant party if Sandra will "persuade" the landlord to get Mary a new refrigerator.

The tenants have a sidewalk sale to pay for the repairs needed to fix up 227. Lester asks Mary not to sell his aunt's old, ugly lamp, but she does anyway, for $5. When Lester finds out, he is upset, but for more reasons than one. The lamp is where he hid the profits of the sale. The tenants get upset with Mary and outcast her. Luckily for her, the wife of the gentleman who bought the lamp comes by her apartment to give it back to Mary, because she did not like the lamp either. They buy it back from the couple for $50 and got the money back to save 227.

Mary is in charge of the church's charity show, and it's like divine providence when the Temptations show up at her door.

When Lester goes to watch the game at a friend's house, Mary and the ladies decide to have a girl's night out. They go to a club/bar where Pearl meets man. They hit it off. When Pearl comes home, she tells Mary that she and Felix are engaged. Mary seems to be the only one concerned about it, while Rose and Sandra want to throw her a bridal shower. Mary thinks that he is after Pearl's money. Pearl doesn't care what Mary thinks, and she and Felix get married any way. When she returns from her honeymoon, Mary apoligizes, but Pearl has bad news. Felix passed away. She admits to Mary that they knew that he was dying. Because she loved him and didn't want him to be lonely, they married so soon.

When Sandra sees a pillow that Mary is making for Brenda, she is impressed. She tells Mary that they could go into business and make lots of money. So Mary agrees to a 50/50 deal with Sandra. Eventually, things become too overwhelming for Mary as she is the one doing all the work and Sandra is the one eating expensive lunches and arranging buyers. Mary insists that she go on the next business lunch with Sandra, and the buer requests 10,000 pillows for his stores. Mary admits to him that they are a small company and they make a deal, with him as a third partner, to build a factory. He decides to build the factory in Taiwan, minus Sandra and Mary. In the end, Sandra ends up owing Mary money because she spent all of the profits.

Rose tries a video-dating service, but wonders if she can live up to the image Sandra creates for her.

When Mary and Rose come home from the movie theater, they see JoJo spray painting his gang tag underneath Pearl's window. Pearl hits him with her pillow, Rose grabs the spray can and accidentally sprays his shirt, and Mary grabs hims, but tries to talk sense into him. JoJo tells his mother everything that happened, while leaving out the part about him spray painting on the building. They decide to sue the ladies, and use Sandra as a witness, who was in the car on a date. When they get in court, his mother and the Judge eventually find out the truth and JoJo is made to clean up his damage. His mother apologizes to the ladies and the ladies are fined 10 cents each.

The 227 residents are worried when Calvin's free-spending new friend offers him a chance to make 50 dollars for doing what ""sounds like a Miami Vice drug deal.""

When Mary's brother Lewis comes to town on business, she decides to set him up on a date with Rose. The next day when Rose won't give Mary any details about the date, they get in to an argument where Rose finally admits that she thinks Mary's brother is "self-centered" and "egotistical". They stop speaking. Meanwhile, Lewis asks Sandra out on a date, and Mary fears that Sandra may be her future sister-in-law.

When Ms. clark uses her feminine wiles to get Brenda a part-time job at Billy Bob's Burgers, Brenda's parents are divided: she wants Brenda to study full time, while he is delighted at her new sense of responsibility.

Sandra is very upset when she learns that her mother is coming to visit. She feels as though her mother doesn't love her because she is so different from her ""normal"" siblings and family members. Sandra changes her appearance to look ""dull"" because she thinks that is what her mother willl approve of. That same weekend, a male friend of hers also comes to visit. Sandra and Mary try to keep the two from meeting. Finally Sandra admits to her mother that she thinks her mother does not love her. Her mom admits that she was just like Sandra before she got married, but calmed down so she could fit in with Sandra's father (who is a minister) and that she loves Sandra just the same because there is never a dull moment with Sandra around. Mop and her mother end up meeting anyway, and they all go dancing.