Season Three of A Different World begins as Whitley (Jasmine Guy) flies back to Hillman after summer vacation. Her travelling companinon is her friend and fellow student Dwayne (Kadeem Hardison), who seems to have changed a great deal in the past few months. Upon arrival, Whitley and Dwayne finds out that Gilbert Hall has gone coed--with Walter (Sinbad) and Jaleesa (Dawnn Lewis) sharing resident-director responsibilities. With this episode, Lou Myers goes from recurring to regular status in the role of Vernon Gaines, owner of that popular campus hangout "The Pit"; also, Reuben Grundy makes his first appearance as incoming student Ernest Bennett.

In desperate need of a math credit to graduate from Hillman, Whitley (Jasmine Guy)j nervously enrolls in the dreaded calculus class run by Col. Taylor (Glynn Turman), aka "Dr. War." Despite his fearsome reputation, Taylor seems genuinely committed to helping Whitley survive the ordeal. And in another development, the friendship between Dwayne (Kadeem Hardison) and Ron (Darryl M. Bell) hits another speed bump when Dwayne accuses Ron of being a spendthrift, and Ron labels Dwayne a tightwad.

Campus discipline is the issue when Walter (Sinbad) temporarily lightens up on the rules governing the male residents of Gilbert Hall, whereupon Jaleesa (Dawnn Lewis) accuses him of exercising a double standard. Before long, all of the dorm residents have taken sides in the argument, divided strictly along gender lines. Meanwhile, Dwayne (Kadeem Hardison) and Freddie (Cree Summer) team up for a research paper, only to find that two heads are not always better than one as the deadline rapidly approaches.

Volunteering to teach dance classes at a community center, Whitley befriends a self-proclaimed poor child named Dion (Brandon Adams in his first regular series appearance)--an accomplished liar who specializes in playing on people's sympathies. Elsewhere, Col. Taylor fills in when Walter is unable to show up for his bowling team, whereupon the other bowlers begin planning a "mutiny" on the maladroit martinet. Appearing as team member "Norm" is former NBA star Norm Nixon, the husband of episode director Debbie Allen, while future Fresh Prince of Bel-Air costar James Avery is cast as the aptly named "Pin Punisher."

When Whitley (Jasmine Guy) announces plans to attend her father's wedding in New York, Dwayne (Kadeem Hardison) offers to drive her there. Actually, Dwayne's primary misison is to visit his former classmate Denise Huxtable (Lisa Bonet, in her first series appearance after leaving A Different World in 1987), hoping to persuade her to return to Hillman College. Ultimately, a depressed Whitley and a disheartened Dwayne find themselves trapped in a blizzard--a crisis that forces them to draw closer together than ever before.

Whitley (Jasmine Guy) had wanted an opera company to perform at an upcoming charity concert, but Dwayne (Kadeem Hardison) has booked the rap group Heavy D & The Boys. Outraged, Whitley organizes a protest--only to humiliate herself when she expresses her anger to the wrong person. Meanwhile, Ron (Darryl M. Bell) falls for his new study partner Elizabeth (Theresa Randle), who has quite a surprise in store for him. Heavy D & the Boys sing "Somebody for Me".

After winning a free honeymoon vacation in Hawaii, Walter (Sinbad) figures that it's time to find himself a wife--so he proposes to Jaleesa (Dawnn Lewis). Though fully aware that it would be merely a marriage of convenience, she accepts. . .and the couple ends up playing out the charade all the way to the altar. Elsewhere on the romantic scene, the relationship between Dwayne (Kadeem Hardison) and Whitley (Jasmine Guy) will never be the same after he kisses her--and she faints dead away.

Defying the wishes of her policeman father (guest star Richard Roundtree), Kim (Charnele Brown) attends the Freaknic music festival--only to be caught in the act when dear old dad shows up for the Hillman homecoming celebration. Kim is outraged by her father's strictness, but Whitley (Jasmine Guy) is curiously unsympathetic to her plight. Meanwhile, the phrase "four's a crowd" takes on a whole new meaning when Dwayne (Kadeem Hardison) and Ron (Darryl M. Bell) bring their respective dates home on the same night.

Just before midterms, Kim (Charnele Brown) receives word that her policeman father (Richard Roundtree) has been seriously wounded on the job. As Dwayne (Kadeem Hardison) and Freddie (Cree Summer) accompany Kim to the hospital, Freddie does her best to bolster Kim's faith in God. But her well-meaning efforts may prove futile when Kim is told the extent of her father's injuries.

Upset that her mother Marion (Diahann Carroll) would rather jet to Paris for Christmas than spend the holidays at home, Whitley takes out anger on her best friends. Thus the stage is set for a Diffreent World spin on "A Christmas Carol", as the Scroogelike Whitley is made to see the foolishness of her wrath during an elaborate Yuletide dream. On this occasion, Mr. Gaines (Lou Myers) is seen as the Ghost of Christmas Past, Walter (Sinbad) shows up as Christmas Present, and Jaleesa (Dawnn Lewis) impersonates Christmas Future.