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

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

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.

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.