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.

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.

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.

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.

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.

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

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.

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!

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.

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.

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.

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.

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 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.

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.

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.

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 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.