Continuing where they last left off, when J.T. believes that Grant is purposing to Janie at a jewelery store and Rita thinks that he should ask Shelly's hand in marriage, it comes down to the party. And after shockingly J.T. and Grant both dramatically propose to Shelly at her birthday party, she must weigh the qualities -- and engagement rings -- of both men in order to decide who she wants to marry and build a future with. Meanwhile, after skipping his flight back to England and staying in the U.S. illegally, Donovan shows up on J.T. and Nick's doorstep, looking for help as he decides what to do next with his life.
After accepting J.T.'s proposal, Shelly giddily starts making plans for the wedding, that is until her mother Beverly (guest star Penny Johnson Jerald) shows up unexpectedly, determined to convince her daughter that marriage is a bad decision. Meanwhile, J.T. gets accepted to medical school. Later, Donovan receives an interesting offer that could allow him to stay in the U.S.
After putting on weight and not being able to fit into her own gown, Shelly decides to wear a client's dress on a date with Jalen (guest star Robert Horry) to the Black and White Ball, only to get caught in it by the customer. Meanwhile, the gang pledges to go on a diet together, but their resolve is put to the test when Janie enlists their help in preparing for her church bake sale.
After Shelly gives Janie a dollar to play the lottery and she wins $5,000, the pair's argument over the money escalates, putting their long friendship in jeopardy. Later, when bad weather forces everyone to stay indoors, the gang's discussion causes some to reevaluate their relationships and beliefs.
When Shelly and Janie refuse to let Rita be the new face of DivaStyle, she threatens to leave the partnership. Meanwhile, Donovan tries to help J.T. and Nick improve their looks by persuading them to use make-up.
As Shelly and Janie prepare to unveil their new DivaStyle clothing line at a big South Beach fashion show, they discover that their former partner Rita will be modeling for their biggest competitor. Meanwhile, Nick begins dating J.T.'s new anatomy class tutor -- against his wishes.
While being interviewed by local news reporter Aramanda De La Cruz (guest star Lauren Sanchez), the girls find out that the manufacturer of their new "DivaStyle Ready To Wear" clothing line runs a sweatshop. Now it's up to the girl's to stop the crazy madness and situation or else they'll be in bigger and more trouble. Meanwhile, Donovan convinces J.T. and Nick to help him sell make-up, motivating them to compete against each other for the biggest sale.
Shelly's return home for Christmas hits an icy patch when she discovers that her mother Beverly (guest star Penny Johnson Jerald) has taken in her favorite student and allowed the teen to move into her old room, make sweeping changes to the family’s holiday traditions and seemingly usurp her relationship with her mom. Meanwhile, J.T., Nick and Donovan decide to skip the hassle of the holidays to watch football, but come to realize how much they miss the yuletide traditions.
J.T.'s new girlfriend gets jealous of his relationships with other women and forces him to choose between her and his friends. Meanwhile, Janie becomes self-conscious about her appearance after a waitress mistakes her for Shelly's mother.
Shelly believes she's unfit to ever be a mother when Janie brings her cousin's infant to DivaStyle and Shelly drops the child. Meanwhile, Nick plays for an all-gay basketball team, but hurts his teammates with his insensitivity.
After each receive a big check from their accountant now that business is booming at DivaStyle, Shelly and Rita try to decide how to spend their sudden windfall, but Janie's dreams of buying something frivolous are put on hold when her husband tells her that he wants to quit his job. Meanwhile, hit with medical school tuition, books and more expenses, J.T. turns to Nick for a loan when he comes up a little short on cash for the month.
Janie's brother Paul visits and makes it evident that he has a crush on Shelly, who, because of their long history, thinks of him as a brother.
Still fond of him and can't get over him, Shelly takes her ex, Grant, the man she almost married, to lunch in an effort to be friends, but finds this a monumental task after he informs her that he's newly engaged and introduces her to his new love. Meanwhile, Nick and J.T. start to hang out with a youngster through a local Big Buddies program, and soon clash over their very different mentoring styles. Later, Rita moves into her new loft.
As if flunking his anatomy exam wasn't enough, an embarrassed J.T. must deal with his cranky instructor Professor Dunson after J.T.'s mother Frances drops by the medical school to beg for a make-up test for her son. But after Shelly advices j.T. to amke his own choice and stand up to his mother, Frances comes to confront Shelly but then the two both decide to work together to get J.T. the chance to take the test over. Meanwhile, after showing promise in a local tournament, Nick tries to convince Janie's husband, Marty, to pursue his dream of being a professional bowler. Later, Shelly tries to help Rita set up her new apartment.
After Rita is trying to persuade a department store buyer, Brenda, to stock their clothing line "Diva Style," Shelly and Jane discover that the buyer is Rita's ex-lesbian lover, so they try to convince Rita to romance her former flame in order to expand their business. Also, after losing an expensive bet to J.T., Donovan enlists Nick's help to win his money back in a rigged poker game.
Shelly's father, Yusef, shows up after years of absence to show his support for Shelly when she is named Miami's Designer of the Year; and to Shelly's surprise, her mother, Beverly, encourages her to give her father a second chance.
Meanwhile, when Janie's curiosity is piqued by the discovery of an unusually large amount of cash in Rita's purse, she decides to investigate the suspicious source of income.
Shelly's mother Beverly finally reveals to Yusef, Shelly's father, that she is pregnant with his child, and Shelly questions his ability to commit to the child.
Meanwhile, when Janie discovers that Rita is secretly hosting Botox parties at the store, she convinces Rita to cut her in on the deal, only to find out that the parties are illegal.