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.

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.

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.

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.

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.

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.

Sandra comes up with a slogan for a new perfume, but she thinks it stinks when her ad-agency boss steals her idea. (tvguide.com)

Travis finds $250,000 left in his limo, and is convinced by Mary & Lester to turn the money in. If the money isn't claimed within 30 days, Travis may keep it. The next day, a beautiful woman named Eartha Kitten comes to the door and claims the money belongs to her boss, and is furious when he learns he turned the money in. Meanwhile, Mary & Lester are heading to Hawaii and have a Bon Voyage party the night before, but the party is interrupted when Eartha's boss (a mob boss) holds everyone hostage. Warren saves the day when he returns disguised as a woman, and pretends to romance Mr Big. Before Travis can return with Mr Big's money, Warren turns the tables on Mr Big and has him arrested.

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 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.

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

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.